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Photoexcitation reactions and the applications of the Vapourtec UV-150 reactor

Photoexcitation is recognised as an underused synthesis tool. A brief look at published literature shows that only about 1% of the published papers in the field of organic syntheses involve a photochemical step. However, in photochemistry courses it is taught that because the chemistry of the excited singlet and triplet states are added to that of the ground state excitation by light multiplies by 3 the accessible reaction paths. It therefore appears that photochemical reactions are significantly less used as they could or should be.

It is Vapourtec’s belief that a major reason for the underutilisation of Photoexcitation is the poor suitability of most batch reaction techniques to photochemical reactions. Continuous Photochemical reactors of the falling film or micro-flow tube style are much better tuned to the photon penetration properties of a typical solution of reagent.

Advantages of Continuous Flow Photoexcitation Reactions

Vapourtec has now made available for both the E-Series and R-Series systems an advanced photochemical reactor intended for continuous flow operation, the UV-150. By eliminating the problems associated with traditional batch photoreactors Vapourtec’s UV-150 enables chemists to take full advantage of the powerful reactions and synthetic routes offered by photo chemical reactions.

The main advantages of flow photoexcitation reactors over conventional batch systems are; consistent light penetrations, controlled exposure times, precise temperature control and removal of the photochemical products from the irradiated area. These features typically result in higher conversions or yields, improved selectivity, enhanced energy efficiencies and reductions of solvent volumes and consequently waste.

Application areas for the Innovative UV-150 Reactor

The UV-150 is a versatile continuous flow photochemical reactor having a broad range of application areas:

Synthesis of Novel Building Blocks
Drug Discovery
Agrochemical Development
Flavours and Flavourings
Research into Solar Chemistry (Artificial Photosynthesis)
Degradation Studies
UV initiated polymerizations
Supramolecular Organic Photochemistry

Full list of photochemical publications citing Vapourtec

Examples of published literature for Photoexcitation reactions and the applications of the Vapourtec UV-150 reactor

Visible-Light-Mediated TiO2-Catalyzed Aerobic Dehydrogenation of N-Heterocycles in Batch and Flow

Junghoon Noh^a, Jun-Young Cho^a, Mincheol Park^b, and Boyoung Y. Park^a

^aDepartment of Fundamental Pharmaceutical Science, Kyung Hee University, Seoul 02447, South Korea

^bDepartment of Biomedical and Pharmaceutical Sciences, Kyung Hee University, Seoul 02447, South Korea

View abstract

Modular Photochemical Flow Synthesis of Structurally Diverse Benzyne and Triazine Precursors

Jorge García-Lacuna^a, Marcus Baumann^a

^aSchool of Chemistry, University College Dublin, Science Centre South, Belfield, Dublin 4, Dublin, Ireland

View abstract

Photo- and Electrochemical Cobalt Catalysed Hydrogen Atom Transfer for the Hydrofunctionalisation of Alkenes

Samikshan Jana¹, Victor Jose Mayerhofer¹, Christopher Teskey²

¹RWTH: Rheinisch-Westfalische Technische Hochschule Aachen, Institute of Organic Chemistry, GERMANY

²RWTH Aachen: Rheinisch-Westfalische Technische Hochschule Aachen, Institute of Organic Chemistry, Landoltweg 1, 52074, Aachen, GERMANY

View abstract

Photochemical Synthesis of Pyrazolines from Tetrazoles in Flow

Adam Burke^a, Silvia Spiccio^a, Mara Di Filippo^a, Marcus Baumann^a

^aSchool of Chemistry, University College Dublin, Science Centre South, D04 N2E2, Dublin, Ireland

View abstract

Flow photochemistry — from microreactors to large-scale processing

Mengxue Zhang^a, Philippe Roth^a

^aCorning SAS, 7 bis avenue de Valvins, CS 70156 Samois sur Seine, 77215 Avon Cedex, France

View abstract

Membrane-based TBADT recovery as a strategy to increase the sustainability of continuous-flow photocatalytic HAT transformations

Zhenghui Wen^a, Diego Pintossi^a, Manuel Nuño^b, Timothy Noël^a

^aFlow Chemistry Group, Van ‘t Hoff Institute for Molecular Sciences, Faculty of Science, University of Amsterdam, Science Park 904, 1098 XH, Amsterdam, The Netherlands

^bVapourtec Ltd., Park Farm Business Centre, Fornham St Genevieve, Bury St Edmunds, Suffolk, IP28 6TS, UK

View abstract

Intraligand Charge Transfer Enables Visible-Light-Mediated Nickel-Catalyzed Cross-Coupling Reactions

Cristian Cavedon^a,b, Sebastian Gisbertz^a,b,Susanne Reischauer^a,b, Sarah Vogl^c, Eric Sperlich^d, John H. Burke^e, Rachel F. Wallick^e, Stefanie Schrottke^f, Wei-Hsin Hsu^a, Lucia Anghileri^a,b, Yannik Pfeifer^d, Noah Richter^a, Christian Teutloff^f, Henrike Müller-Werkmeister^d, Dario Cambié^a, Peter H. Seeberger^a,b, Josh Vura-Weis^e, Renske M. van der Veen^e,g, Arne Thomas^c, Bartholomäus Pieber^a

^aDepartment of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany

^bDepartment of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin, Germany

^cDepartment of Chemistry, Functional Materials, Technische Universität Berlin, Hardenbergstraße 40, 10623 Berlin, Germany

^dInstitute of Chemistry, University of Potsdam, Karl-Liebknecht-Strasse 24–25, 14476 Potsdam, Germany

^eDepartment of Chemistry, University of Illinois Urbana-Champaign, Urbana, Illinois, 61801 USA

^fDepartment of Physics, Freie Universität Berlin, Arnimallee 22, 14195 Berlin, Germany

^gHelmholtz Zentrum Berlin für Materialien und Energie GmbH, Hahn-Meitner-Platz 1, 14109 Berlin, Germany

View abstract

Taming photocatalysis in flow: easy and speedy preparation of α-aminoamide derivatives

Ricardo I. Rodríguez^a, Marina Sicignano^a, Montaña J. García^a, Rodrigo G. Enríquez^a, Silvia Cabrera^b,c, José Alemán^a,c,d

^aOrganic Chemistry Department, Science Faculty, Universidad Autónoma de Madrid, Madrid-28049, Spain

^bInorganic Chemistry Department, Science Faculty, Universidad Autónoma de Madrid, Madrid-28049, Spain

^cInstitute for Advanced Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, 28049 Madrid, Spain

^dCenter for Innovation in Advanced Chemistry (ORFEO-CINQA), Universidad Autónoma de Madrid, Spain

View abstract

Flow synthesis of photocatalytic semiconductor–metal hybrid nanocrystals

Tal Cohen^a,b, Nir Waiskopf^a,b, Adar Levi^a,b, David Stone^a,b, Sergei Remennik^b, Uri Banin^a,b

^aThe Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem 91904, Israel

^bThe Center for Nanoscience and Nanotechnology, The Hebrew University of Jerusalem, Jerusalem 91904, Israel

View abstract

Statistical optimization modeling of organic dye photodegradation process using slag nanocomposite

Kingsley Safo^a, Hussien Noby^a,b, Mitsuhara Matatoshi^c, Hiroshi Naragino^c, Ahmed H. El-Shazly^a,d

^aDepartment of Chemical and Petrochemicals Engineering, Egypt-Japan University of Science and Technology, New Borg Al-Arab City, Alexandria, Egypt

^bMaterials Engineering and Design, Faculty of Energy Engineering, Aswan University, Aswan, Egypt

^cInterdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasuga Kouen, Kasuga, Fukuoka, 816-8580, Japan

^dDepartment of Chemical Engineering, Faculty of Engineering, Alexandria University, Alexandria, Egypt

View abstract

Heterogeneous metallaphotoredox catalysis in a continuous-flow packed bed reactor

Wei-Hsin Hsu^a,b, Susanne Reischauer^a,b, Peter H Seeberger^a,b, Bartholomäus Pieber^a, Dario Cambié^a

^aMax Planck Institute of Colloids and Interfaces, Biomolecular Systems Department, Am Mühlenberg 1, 14476 Potsdam, Germany

^bFreie Universität Berlin, Institute for Chemistry and Biochemistry, Arnimallee 22, 14195 Berlin, Germany

View abstract

Total Synthesis of Phytotoxic Radulanin A Facilitated by the Photochemical Ring Expansion of a 2,2-Dimethylchromene in Flow

Bruce Lockett-Walters^a, Simon Thuillier^a,b, Emmanuel Baudouin^b, Bastien Nay*^a

^aLaboratoire de Synthèse Organique, Ecole Polytechnique, CNRS, Institut Polytechnique de Paris, 91128 Palaiseau, France

^bInstitut de Biologie Paris-Seine (IBPS), Laboratoire de Biologie du Développement, Sorbonne Université, CNRS, UMR7622, F-75005 Paris, France

View abstract

Practical Ferrioxalate Actinometry for the Determination of Photon Fluxes in Production-Oriented Photoflow Reactors

Bavo Vandekerckhove^a, Nicola Piens^b, Bert Metten^b, Christian V. Stevens^a, Thomas S. A. Heugebaert*^a

^aSynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium

^bAjinomoto Bio-Pharma Services, Cooppallaan 91, 9230 Wetteren, Belgium

View abstract

Total synthesis of phytotoxic radulanin A facilitated by the photochemical ring expansion of a 2,2-dimethylchromene in flow

Bruce Lockett-Walters¹, Simon Thuillier^1,2, Emmanuel Baudouin², Bastien Nay*¹

¹Laboratoire de Synthèse Organique, Ecole Polytechnique, CNRS, Institut Polytechnique de Paris, 91128 Palaiseau, France

²Sorbonne Université, CNRS, Institut de Biologie Paris-Seine (IBPS), Laboratoire de Biologie du Développement, UMR7622, F-75005, Paris, France

View abstract

Selective Photochemical Continuous Flow Benzylic Monochlorination

Robbie Radjagobalou^a, Miguel Imbratta^b, Julie Bergraser^b, Marion Gaudeau^b, Gildas Lyvinec^b, Dominique Delbrayelle^b, Olivier Jentzer^b, Jérémy Roudin^a, Benjamin Laroche^a, Stéphanie Ognier^a, Michael Tatoulian^a, Janine Cossy^a, Pierre-Georges Echeverria^b

^aParis FLOW Tech − PSL, ENSCP, 11 rue Pierre et Marie Curie, Paris 75005, France

^bMinakem Recherche, 145 Chemin des Lilas, Beuvry-La-Forêt 59310, France

View abstract

Photocatalytic Approach to α,α-Difluoroalkyl Alcohols

Georgii Kachkovskyi^a, Marcin Cieślak^a, Piotr Graczyk^a, Przemysław Zawadzki^a, Justyna Kalinowska-Tłuścik^b, Mateusz Werłos^a,b

^aSelvita SA., Bobrzyńskiego 14, 30-348 Kraków, Poland

^bFaculty of Chemistry Jagiellonian University, Gronostajowa 2, 30-387 Krakow, Poland

View abstract

Continuous-Flow Synthesis of Alkyl Zinc Sulfinates for the Direct Photofunctionalization of Heterocycles

José Luis Nova-Fernández^a,b, Montaña J. García^a, Leonardo Mollari^a, Gustavo Pascual-Coca^b, Silvia Cabrera^c,d,e, José Alemána^d,e

^aOrganic Chemistry Department, M1, Universidad Autónoma de Madrid, 28049, Madrid, Spain.

^bSynthelia Organics Labs, C/ Faraday, 7, Labs 2.05 and 0.03, Parque Científico de Madrid, 28049, Madrid, Spain.

^cInorganic Chemistry Department, M7, Universidad Autónoma de Madrid, 28049, Madrid, Spain.

^dInstitute for Advanced Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, 28049, Madrid, Spain.

^eCenter for Innovation in Advanced Chemistry (ORFEO-CINQA), Universidad Autónoma de Madrid.

View abstract

Chip-Scale Solar-Thermal-Electrical Power Generation

Zhihang Wang¹, Zhenhua Wu², Zhiyu Hu², Jessica Orrego-Hernandez¹, Erzhen Mu³, Zhao-Yang Zhang⁴, Martyn Jevric¹, Yang Liu², Xuecheng Fu⁵, Fengdan Wang⁵, Tao Li⁴, Kasper Moth-Poulsen¹

¹Chalmers University of Technology - Department of Chemistry and Chemical Engineering

²Shanghai Jiao Tong University (SJTU) - National Key Laboratory of Science and Technology on Micro/Nano Fabrication

³Henan Polytechnic University - School of Materials Science and Engineering

⁴Shanghai Jiao Tong University (SJTU) - Shanghai Key Laboratory of Electrical Insulation and Thermal Aging

⁵Shanghai Jiao Tong University (SJTU) - Center for Advanced Electronic, Materials and Devices (AEMD)

View abstract

Photoredox Iridium–Nickel Dual Catalyzed Cross-Electrophile Coupling: From a Batch to a Continuous Stirred-Tank Reactor via an Automated Segmented Flow Reactor

Rohit Duvadie^a, Alexander Pomberger^b, Yiming Mo^b, Erhan I. Altinoglu^c, Hsiao-Wu Hsieh^a, Kakasaheb Y. Nandiwale^a, Victor L. Schultz^b, Klavs F. Jensen^b, Richard I. Robinson^a

^aGlobal Discovery Chemistry, Novartis Institutes for Biomedical Research, 250 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States

^bDepartment of Chemical Engineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States

^cChemical and Pharmaceutical Profiling, Novartis Global Drug Development, 700 Main Street South, Cambridge, Massachusetts 02139, United States

View abstract

Optimizing the Performance of the Meso-Scale Continuous-Flow Photoreactor for Efficient Photocatalytic CO2 Reduction with Water Over Pt/TiO2/RGO Composites

Samar Nabil^a, Elsayed A. Shalaby^a, Marwa F. Elkady^b,c, Yoshihisa Matsushita^d, Ahmed H. El-Shazly^b,e

^aDepartment of Environmental Studies, Institute of Graduate Studies and Research, Alexandria University, Alexandria, 21526, Egypt

^bChemical and Petrochemicals Engineering Department, Egypt-Japan University of Science and Technology, Alexandria, 21934, Egypt

^cFabrication Technology Department, Advanced Technology and New Materials Research Institute (ATNMRI), City of Scientific Research and Technological Applications, Alexandria, Egypt

^dEgypt-Japan University of Science and Technology, 179 New Borg El‐Arab, Alexandria, 21934, Egypt

^eChemical Engineering Department, Faculty of Engineering, Alexandria University, Alexandria, 21544, Egypt

View abstract

Dimeric cyclobutane formation under continuous flow conditions using organophotoredox catalysed [2+2]-cycloaddition

Helena F. Grantham^a, Marc C. Kimber^a

^aSchool of Science, Department of Chemistry, Loughborough University, LE11 3TU, UK

View abstract

Synthesis of 2H-Indazoles via the Cadogan Reaction in Batch and Flow Mode

Matilda Duffy^a, Mara Di Filippo^a, Marcus Baumann^a

^aUniversity College Dublin, School of Chemistry, Science Centre South, Dublin D04 N2E5, Ireland

View abstract

Photocatalysis in the Life Science Industry

Lisa Candish^a, Karl D. Collins^b, Gemma C. Cook^c, James J. Douglas^d, Adrián Gómez-Suárez^e, Anais Jolit^f, Sebastian Keess^f

^aDrug Discovery Sciences, Pharmaceuticals, Bayer AG, 42113 Wuppertal, Germany

^bBayer Foundation, Public Affairs, Science and Sustainability, Bayer AG, 51368 Leverkusen, Germany

^cDiscovery High-Throughput Chemistry, Medicinal Science and Technology, GlaxoSmithKline, Stevenage SG1 2NY, U.K.

^dEarly Chemical Development, Pharmaceutical Sciences, R&D, AstraZeneca, Macclesfield SK10 2NA, U.K.

^eOrganic Chemistry, Bergische Universität Wuppertal, 42119 Wuppertal, Germany

^fMedicinal Chemistry Department, Neuroscience Discovery Research, AbbVie Deutschland GmbH & Co. KG, 67061 Ludwigshafen, Germany

View abstract

Photoredox-Catalyzed Multicomponent Petasis Reaction in Batch and Continuous Flow with Alkyl Boronic Acids

Monica Oliva¹, Prabhat Ranjan¹, Serena Pillitteri¹, Guglielmo Attilio Coppola¹, Monica Messina¹, Erik V. Van der Eycken^1,2, Upendra Kumar Sharma¹

¹Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven B-3001, Belgium

²Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya street 6, Moscow RU-117198, Russia

View abstract

Photoredox-Catalyzed Dehydrogenative Csp3–Csp2 Cross-Coupling of Alkylarenes to Aldehydes in Flow

Oliver M. Griffiths^a, Henrique A. Esteves^a, Yiding Chen^a, Karin Sowa^a,b, Oliver S. May^a, Peter Morse^c, David C. Blakemore^c, Steven V. Ley*^a

^aYusuf Hamied Department of Chemistry, University of Cambridge, CB2 1EW Cambridge, U.K.

^bDepartment of Chemistry, University of Münster, 48149 Münster, Germany

^cMedicine Design, Pfizer, Inc., Groton, Connecticut 06340, United States

View abstract

Homogeneous Catalytic C(sp3 )–H Functionalization of Gaseous Alkanes

Antonio Pulcinella^a, Daniele Mazzarella^a, Timothy Noël^a

^aFlow Chemistry Group, Van ’t Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam

View abstract

Unlocking the Accessibility of Alkyl Radicals from Boronic Acids through Solvent-Assisted Organophotoredox Activation

Prabhat Ranjan^a, Serena Pillitteri^a, Guglielmo Coppola^a, Monica Oliva^a, Erik V. Van der Eycken^a,b, Upendra K. Sharma^a

^aLaboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, B-3001 Leuven, Belgium

^bPeoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya Street 6, 117198 Moscow, Russia

View abstract

Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

Laura Buglioni^a,b, Fabian Raymenants^a, Aidan Slattery^a, Stefan D. A. Zondag^a, Timothy Noël^a

^aFlow Chemistry Group, van ’t Hoff Institute for Molecular Sciences (HIMS), Universiteit van Amsterdam (UvA), Science Park 904, 1098 XH, Amsterdam, The Netherlands

^bMicro Flow Chemistry and Synthetic Methodology, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, Het Kranenveld, Bldg 14—Helix, 5600 MB, Eindhoven, The Netherlands

View abstract

Scalability of photochemical reactions in continuous flow mode

Kian Donnelly^a, Marcus Baumann^a

^aSchool of Chemistry, Science Centre South, University College Dublin, D04 N2E2, Dublin, Ireland

View abstract

(Trifluoromethylselenyl)methylchalcogenyl as Emerging Fluorinated Groups: Synthesis under Photoredox Catalysis and Determination of the Lipophilicity

Kevin Grollier^[a], Arnaud De Zordo-Banliat^[b], Flavien Bourdreux^[b], Bruce Pegot^[b], Guillaume Dagousset^[b], Emmanuel Magnier^*[b], Thierry Billard*^{[a, c]}

^[a]Institute of Chemistry and Biochemistry (ICBMS, UMR CNRS 5246) Univ Lyon, Universite Lyon 1, CNRS,CPE, INSA43 Bd du 11 novembre 1918, 69622 Villeurbanne (France)

^[b]InstitutLavoisierdeVersailles (UMR CNRS 8180)Universit Paris-Saclay,UVSQ,CNRS78035 Versailles (France)

^[c]CERMEP-In vivo imaging59 Bd Pinel, 69677 Lyon (France)

View abstract

A revised 1D equivalent model for the determination of incident photon flux density in a continuous-flow LED-driven spiral-shaped microreactor using the actinometry method with Reinecke’s salt

Robbie Radjagobalou^a, Victoria Dias Da Silva Freitas^a, Jean-François Blanco^a, Fabrice Gros^b, Jérémy Dauchet^b, Jean-François Cornet^b, Karine Loubiere^a

^aLaboratoire de Génie Chimique (LGC), Université de Toulouse, CNRS, INPT, UPS, 4 allée Emile Monso, CS 84234, 31 432, Toulouse, France

^bUniversité Clermont Auvergne, Clermont Auvergne INP, CNRS, Institut Pascal, F-63000, Clermont-Ferrand, France

View abstract

Discrete Ti−O−Ti Complexes: Visible-Light-Activated, Homogeneous Alternative to TiO2 Photosensitisers

Kira Behm^a, Dr. Eszter Fazekas^a, Prof. Martin J. Paterson^a, Dr. Filipe Vilela^a, Dr. Ruaraidh D. McIntosh^a

^aInstitute of Chemical Sciences, Heriot-Watt University, Edinburgh, EH14 4AS UK

View abstract

Radical alpha-Trifluoromethoxylation of Ketones by Means of Organic Photoredox Catalysis

Thibaut Duhail^[a]†, Tommaso Bortolato^[b]†, Javier Mateos^[b], Elsa Anselmi^[a,c], Benson Jelier^[d], Antonio Togni^[d], Emmanuel Magnier^[a], Guillaume Dagousset^[a], Luca Dell’Amico^[b]

^[a] Université Paris-Saclay, UVSQ, CNRS, UMR 8180, Institut Lavoisier de Versailles, 78035 Versailles Cedex (France)

^[b]Department of Chemical Sciences, University of Padova, Via Marzolo 1, 35131, Padova (Italy)

^[c] Université de Tours, Faculté des Sciences et Techniques, 37200 Tours (France)

^[d]Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zurich, Vladimir-Prelog-Weg 2, 8093 Zurich (Switzerland)

View abstract

Rapid Optimization of Photoredox Reactions for Continuous-Flow Systems Using Microscale Batch Technology

María González-Esguevillas^a, David F. Fernández^a, Juan A. Rincón^b, Mario Barberis^b, Oscar de Frutos^b, Carlos Mateos^b, Susana García-Cerrada^b, Javier Agejas^b, David W. C. MacMillan*^a

^aMerck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States

^bCentro de Investigación Eli Lilly, S. A., Avda. de la Industria 30, 28108 Alcobendas, Madrid, Spain

View abstract

Modular allylation of C(sp3)−H bonds by combining decatungstate photocatalysis and HWE olefination in flow

Luca Capaldo¹, Stefano Bonciolini¹, Antonio Pulcinella¹, Manuel Nuño², Timothy Noël¹

¹ Flow Chemistry Group, van ’t Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands

²Vapourtec Ltd., Park Farm Business Centre, Fornham St Genevieve, Bury St Edmunds, Suffolk IP28 6TS, United Kingdom

View abstract

A continuous flow synthesis of [1.1.1]propellane and bicyclo[1.1.1]pentane derivatives

Kian Donnelly, Marcus Baumann

School of Chemistry, University College Dublin, Science Centre South, Belfield, Ireland

View abstract

Development of a Continuous Photochemical Benzyne-Forming Process

Cormac Bracken^a, Andrei S. Batsanov^b, Marcus Baumann^a

^aSchool of Chemistry, University College Dublin, Science Centre South, D04 N2E2, Dublin, Ireland

^bDepartment of Chemistry, University of Durham, South Road, DH1 3LE, Durham, UK

View abstract

A scalable continuous photochemical process for the generation of aminopropylsulfones

Stefano Bonciolini^a, Mara Di Filippo^a, Marcus Baumann^a

^aSchool of Chemistry, University College Dublin, Science Centre South, Belfield, Ireland

View abstract

Continuous Flow Photo-RAFT and Light-PISA

Jian Wang^a,c, Xin Hu^b,c, Ning Zhu^a,c, Kai Guo^c

^aCollege of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing, Jiangsu 211800, China

^bCollege of Materials Science and Engineering, Nanjing Tech University, Nanjing, Jiangsu 211800, China

^cState Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, Nanjing, Jiangsu 211800, China

View abstract

Photochemical Flow Oximation of Alkanes

Oliver M. Griffiths^{a, b}, Michele Ruggeri^a, Ian R. Baxendale∗^a

^aDepartment of Chemistry, University of Durham, South Road, Durham, Durham, DH1 3LE, UK

^bDepartment of Chemistry, Cambridge University, South Road, Cambridge, Cambridgeshire, CB2 1EW, UK

View abstract

Continuous Flow Synthesis of Quinolines via a Scalable Tandem Photoisomerization-Cyclization Process

Mara Di Filippo, Marcus Baumann

School of Chemistry, University College Dublin, Science Centre South, Belfield, Dublin D04 N2E2, Ireland

View abstract

Two Colour Photoflow Chemistry for Macromolecular Design

Matthias Van De Walle, Kevin De Bruycker, James P. Blinco, Christopher Barner-Kowollik

Centre for Materials Science, School of Chemistry and Physics, Queensland University of Technology (QUT)2 George St., Brisbane, QLD 4000 (Australia)

View abstract

C(sp3)–H functionalizations of light hydrocarbons using decatungstate photocatalysis in flow

Gabriele Laudadio^1*, Yuchao Deng^1,2,3,*, Klaas van der Wal¹, Davide Ravelli⁴, Manuel Nuño⁵, Maurizio Fagnoni⁴, Duncan Guthrie⁵, Yuhan Sun^2,3, Timothy Noël^1,†

¹Micro Flow Chemistry and Synthetic Methodology, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, Eindhoven, Netherlands.

²School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, P. R. China.

³Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201210, P. R. China.

⁴PhotoGreen Lab, Department of Chemistry, University of Pavia, Pavia 27100, Italy.

⁵Vapourtec, Fornham St Genevieve, Bury St Edmunds, Suffolk IP28 6TS, UK.

^†Corresponding author. Email: [email protected]

^*These authors contributed equally to this work.

View abstract

Visible Light Mediated N-Desulfonylation of N-Heterocycles using a Heteroleptic Copper (I) Complex as a Photocatalyst

Cameron J. Hunter, Michael J. Boyd, Gregory D. May, Robert Fimognari*

Vertex Pharmaceuticals Incorporated, 50 Northern Avenue, Boston, Massachusetts 02210, United States

View abstract

Photocatalytic α‐Tertiary Amine Synthesis via C–H Alkylation of Unmasked Primary Amines

Alison S. H. Ryder^a, William B. Cunningham^b, George Ballantyne^b, Tom Mules^b, Anna G. Kinsella^b, Jacob Turner-Dore^b, Catherine M. Alder^c, Lee J. Edwards^c, Blandine S. J. McKay^c, Matthew N. Grayson^b, Alexander J. Cresswell^b*

^aCentre for Sustainable Chemical Technologies, 1 South, University of Bath, Claverton Down, Bath, BA2 7AY (UK)

^bDepartment of Chemistry, 1 South, University of Bath, Claverton Down, Bath, BA2 7AY (UK)

^cMedicines Design, GSK Medicines Research Centre, Gunnels Wood Rd, Stevenage, SG1 2NY (UK)

View abstract

Photon Equivalents as a Parameter for Scaling Photoredox Reactions in Flow: Translation of Photocatalytic C−N Cross‐Coupling from Lab Scale to Multikilogram Scale

Emily B. Corcoran^*a, Jonathan P. McMullen^*b, François Lévesque^b, Michael K. Wismer^c, John R. Naber^b

^aProcess Research & Development, Merck & Co., Inc., Boston, MA 02115 (USA)

^bProcess Research & Development, Merck & Co., Inc., Rahway, NJ 07065 (USA)

^cScientific Engineering & Design, Merck & Co., Inc., Kenilworth, NJ 07033 (USA)

View abstract

Continuous Flow Photochemistry for the Preparation of Bioactive Molecules

Mara Di Filippo, Cormac Bracken, Marcus Baumann*

School of Chemistry, University College Dublin, Science Centre South, Belfield, Dublin 4, Ireland

View abstract

Development of a Continuous Flow Photoisomerization Reaction Converting Isoxazoles into Diverse Oxazole Products

Cormac Bracken, Marcus Baumann*

School of Chemistry, University College Dublin, Science Centre South, Belfield, Dublin 4, Ireland

View abstract

Development of a Continuous Flow Photoisomerization Reaction Converting Isoxazoles into Diverse Oxazole Products

Cormac Bracken, Marcus Baumann

School of Chemistry, University College Dublin, Science Centre South, Belfield, Dublin 4, Ireland

View abstract

Continuous Flow Enables Metallaphotoredox Catalysis in a Medicinal Chemistry Setting: Accelerated Optimization and Library Execution of a Reductive Coupling between Benzylic Chlorides and Aryl Bromides

Zachary G. Brill, Casey B. Ritts, Umar Faruk Mansoor, Nunzio Sciammetta

Department of Discovery Chemistry, MRL, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, MA 02115 USA

View abstract

Metal‐Free Visible‐Light‐Mediated Hydrotrifluoromethylation of Unactivated Alkenes and Alkynes in Continuous Flow

Anne‐Laure Barthelemy Guillaume Dagousset Emmanuel Magnier

View abstract

Lilly Research Award Program (LRAP): A Successful Academia–Industry Partnership Model in the Context of Flow Chemistry for Drug Discovery

Mateos, Carlos
View abstract

Photochemical flow synthesis of 3‐hydroxyazetidines

Michele Ruggeri¹, Amanda Worthy Dombrowski², Stevan W. Djuric², Ian Richard Baxendale¹

¹University of Durham, Department of Chemistry, South Road, DH1 3LE Durham, UNITED KINGDOM

²AbbVie, Inc., 1 North Waukegan Road, North Chicago, IL 60064 Chicago, UNITED STATES

View abstract

Visible‐Light‐Mediated Cross‐Couplings and C–H Activation via Dual Photoredox/Transition‐Metal Catalysis in Continuous‐Flow Processes

Soo Dong Kim, Jonghyun Lee, Nam-Jung Kim, Boyoung Park

Kyung Hee University, Department of Pharmacy, Kyungheedaero 26, 02447 Seoul, Republic of Korea

View abstract

A Photoredox Coupling Reaction of Benzylboronic Esters and Carbonyl Compounds in Batch and Flow

Yiding Chen^†, Oliver May^†, David C. Blakemore^‡, and Steven V. Ley^†*

^† Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, U.K.

^†‡ Medicine Design, Pfizer Inc., Eastern Point Road, Groton, Connecticut 06340, United States

View abstract

Conjugated porous polymers for photocatalytic applications

Y. L. Wong^a, J. M. Tobin^b, Z. Xu^a, F. Vilela^*b

^aDepartment of Biology and Chemistry, City University of Hong Kong, 83 Tat Chee Avenue, Kowloon, Hong Kong

^bSchool of Engineering and Physical Sciences, Heriot Watt University, Edinburgh, UK

View abstract

A Simple and Efficient Flow Preparation of Pyocyanin a Virulence Factor of Pseudomonas aeruginosa

Frederik B. Mortzfeld^a,b, Jörg Pietruszka^b, Ian R. Baxendale*^a

^aDepartment of Chemistry, University of Durham, South Road, Durham, Durham, DH1 3LE, UK

^bInstitut für Bioorganische Chemie, Heinrich‐Heine‐Universität Düsseldorf im Forschungszentrum Jülich, 52425, Jülich, Deutschland

View abstract

Visible light‐promoted Fe‐catalyzed Csp2‐Csp3 Kumada cross‐coupling in flow

Xiao-Jing Wei^a, Irini Abdiaj^b, Carlo Sambiagio^a, Chenfei Li^c, Eli Zysman-Colman^c, Jesús Alcázar^b, Timothy Noël^a

^a Department of Chemical Engineering and Chemistry Micro Flow Chemistry and Synthetic Methodology Eindhoven University of Technology Den Dolech 2, 5612 AZ Eindhoven (The Netherlands)

^b Discovery Sciences, Janssen Research and Development Jannsen-Cilag, S.A. Jarama 75A, 45007 Toledo (Spain)

^c Organic Semiconductor Center, EaStCHEM School of ChemistryUniversity of St Andrews, St Andrews, Fife, KY16 9ST (UK).

View abstract

Practical and regioselective amination of arenes using alkyl amines

Alessandro Ruffoni ¹, Fabio Juliá ¹, Thomas D. Svejstrup ¹, Alastair J. McMillan ¹, James J. Douglas ², Daniele Leonori ¹

¹ School of Chemistry, University of Manchester, Manchester, UK.

² Early Chemical Development, Pharmaceutical Sciences, IMED Biotech Unit,AstraZeneca, Macclesfield, UK

View abstract

Additive manufacturing of photoactive polymers for visible light harvesting

Adilet Zhakeyev^ac, John Tobin^a, Huizhi Wang^b, Filipe Vilela^a, Jin Xuan^ac

^a School of Engineering and Physical Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, UK

^b Department of Mechanical Engineering, Imperial College London, Exhibition Road, South Kensington Campus, London, SW7 2AZ, UK

^c Department of Chemical Engineering, Loughborough University, Loughborough, UK

View abstract

Protection‐Group‐Free Synthesis of Sequence‐Defined Macromolecules via Precision λ‐Orthogonal Photochemistry

Waldemar Konrad^1,2, Christian Fengler^1,2, Sarrah Putwa¹, Christopher Barner-Kowollik^1,2

¹Macromolecular Architectures, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, 76131 Karlsruhe, Germany

²School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology (QUT), 2 George Street, QLD, 4000 Brisbane, Australia

View abstract

Decarboxylative Intramolecular Arene Alkylation Using N-(Acyloxy)phthalimides, an Organic Photocatalyst, and Visible Light

Trevor C. Sherwood^*†, Hai-Yun Xiao^*†, Roshan G. Bhaskar^†, Eric M. Simmons^‡, Serge Zaretsky^‡, Martin P. Rauch^§, Robert R. Knowles^§, T. G. Murali Dhar^†

^† Research and Development, Bristol-Myers Squibb Company, P.O. Box 4000, Princeton, New Jersey 08543-4000, United States

^‡ Chemical and Synthetic Development, Bristol-Myers Squibb, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States

^§Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States

View abstract

Visible Light‐Promoted Beckmann Rearrangements: Separating Sequential Photochemical and Thermal Phenomena in a Continuous Flow Reactor

Yuesu Chen, David Cantillo, C. Oliver Kappe

Karl-Franzens-Universitat Graz, Institute of Chemistry, 8010 Graz, AUSTRIA

View abstract

Towards a Scalable Synthesis of 2‐Oxabicyclo[2.2.0]hex‐5‐en‐3‐one Using Flow Photochemistry

Jason D. Williams^a,b, Yuma Otake^a, Guilhem Coussanes^c, Iakovos Saridakisc^c, Nuno Maulidec^c, C. Oliver Kappea^a,b

^a Center for Continuous Flow Synthesis and Processing (CC FLOW), Research Center Pharmaceutical Engineering GmbH (RCPE), Inffeldgasse 13, 8010 Graz, Austria

^b Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, 8010 Graz, Austria

^c Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090 Vienna, Austria

View abstract

Rapid Photochemical Reaction Studies under Continuous-flow Conditions in the Vapourtec UV-150 Reactor-A Technical Note

Richard Hunter^a, Sam Josland^a, Joseph Moore^b, Duncan Guthrie^b, Mark J. Robertson^a, Michael Oelgemöller^a

^a College of Science and Engineering, James Cook University, Townsville, QLD 4911, Australia

^b Vapourtec Ltd, Park Farm Business Centre, Fornham St Genevieve, Bury St Edmunds, Suffolk, IP28 6TS, UK

View abstract

Enabling synthesis in fragment-based drug discovery by reactivity mapping: photoredox-mediated cross-dehydrogenative heteroarylation of cyclic amines

Rachel Grainger^*a, Tom D. Heightman^a, Steven V. Ley^b, Fabio Lima^b,c, Christopher N. Johnson^*a

^a Astex Pharmaceuticals, 436 Cambridge Science Park, Milton Road, Cambridge, UK

^b Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK

^c Novartis Pharma AG, Novartis Campus, 4002 Basel, Switzerland

View abstract

A Laser Driven Flow Chemistry Platform for Scaling Photochemical Reactions with Visible Light

Kaid C. Harper, Eric G. Moschetta, Shailendra V. Bordawekar, Steven J. Wittenberger

Process Research and Development, AbbVie Inc., 1 North Waukegan Road, North Chicago, Illinois 60064, United States

View abstract

De novo design of organic photocatalysts: bithiophene derivatives for the visible‐light induced C‐H functionalization of heteroarenes

Cecilia Bottecchia¹, Raul Martin², Irini Abdiaj³, Ettore Crovini⁴, Jesus Alcazar³, Jesus Jorduna, Maria Blesa, Jose Carrillo³, Pilar Prieto, Timothy Noel¹

¹ TU Eindhoven, Netherlands

² Universidad de Castilla-La Mancha Facultad de Ciencias y Tecnologias Quimicas de Ciudad Real, Spain

³ Janssen Research and Development, Spain

⁴ University of Saint Andrews School of Chemistry, United Kingdom

View abstract

Recent Advances in Photodecarboxylations Involving Phthalimides

Saira Mumtaz, Mark J. Robertson, Michael Oelgemöller

James Cook University, College of Science and Engineering, Townsville, Qld 4811, Australia.

View abstract

C–H functionalisation of aldehydes using light generated, non-stabilised diazo compounds in flow

Paul Dingwall ^a, Andreas Greb ^a, Lorène N. S. Crespin ^a, Ricardo Labes ^a, Biagia Musio ^a, Jian-Siang Poh ^a, Patrick Pasau ^b, David C. Blakemore ^c, Steven V. Ley ^*a

^a Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK.

^b UCB Biopharma SPRL, Chemical Research R5, Chemin du Foriest 1420, Braine-L’Alleud, Belgium

^c Medicine Design, Pfizer Inc., Eastern Point Road, Groton, Connecticut 06340, USA

View abstract

Photoinduced Palladium Negishi Cross-Coupling Through Visible Light Absorption of Palladium-Organozinc complexes

Irini Abdiaj ^a, Lena Huck ^a,b, José Miguel Mateo ^b, Antonio de la Hoz ^b, M. Victoria Gomez ^c, Angel Díaz-Ortiz ^b, Jesús Alcázar ^a

^a Lead Discovery, Janssen Research and Development, Janssen-Cilag, S.A., Jarama 75A, 45007 Toledo, Spain

^b Facultad de Ciencias y Tecnologías Químicas, Universidad de Castilla-La Mancha, Av. Camilo José Cela 10, 13071 Ciudad Real, Spain

^c Instituto Regional de Investigación Científica Aplicada, Universidad de Castilla-La Mancha, Av. Camilo José Cela, sn, 13071 Ciudad Real, Spain

View abstract

Three-Component Assembly of Multiply Substituted Homoallylic Alcohols and Amines Using a Flow Chemistry Photoreactor

Yiding Chen ^†, David Blakemore ^‡, Patrick Pasau ^§, Steven V. Ley ^†

^† Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, U.K.

^‡ Medicine Design, Pfizer Inc., Eastern Point Road, Groton, Connecticut 06340, United States

^§ UCB Biopharma SPRL, Chemical Research R5, Chemin du Foriest, 1420 Braine-L’Alleud, Belgium

View abstract

Continuous Flow Photochemical Benzylic Bromination of a Key Intermediate in the Synthesis of a 2‐Oxazolidinone

Yuesu Chen^{a, b}, Oscar de Frutos^c, Carlos Mateos^c, Juan A. Rincon^c, David Cantillo^{*a, b}, C. Oliver Kappe^{*a, b}

^a Center for Continuous Flow Synthesis and Processing (CC FLOW), Research Center Pharmaceutical Engineering GmbH (RCPE), Inffeldgasse 13, 8010 Graz (Austria)

^b Institute of Chemistry, University of Graz, Heinrichstrasse 28, 8010, Graz (Austria)

^c Centro de Investigacin Lilly S. A. Avda. de la Industria 30, 28108 Alcobendas-Madrid (Spain)

View abstract

Native Chemical Ligation–Photodesulfurization in Flow

Timothy S. Chisholm, Daniel Clayton, Luke J. Dowman, Jessica Sayers, Richard J. Payne

School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia

View abstract

Combining CH functionalisation and flow photochemical heterocyclic metamorphosis (FP-HM) for the synthesis of benzo [1, 3] oxazepines

Jasraj S. Babra, Andrew T. Russell, Christopher D. Smith, Yuxiong Zhang

Department of Chemistry, University of Reading, Whiteknights, Reading, RG6 6AD, UK

View abstract

Studies toward the scaling of gas‐liquid photocycloadditions

Dr. Emily B. Corcoran, Dr. François Lévesque, Dr. Jonathan P. McMullen, Dr. John R. Naber

Department of Process Research and Development, Merck Sharp & Dohme Corp., Rahway, USA

View abstract

Photooxygenation in an advanced led-driven flow reactor module: Experimental investigations and modelling

Robbie Radjagobalou^ab, Jean-François Blanco^a, Odile Dechy-Cabaret^b, Michael Oelgemöller^c, Karine Loubière^a

^a Laboratoire de Génie Chimique LGC, Université de Toulouse, CNRS, Toulouse, France

^b Laboratoire de Chimie de Coordination LCC, CNRS, Toulouse, France

^c James Cook University, College of Science and Engineering, Townsville, Queensland 4811, Australia

View abstract

Dichlorophenylacrylonitriles as AhR Ligands displaying selective breast cancer cytotoxicity in vitro

Jennifer R Baker¹, Jayne Gilbert², Stefan Paula³, Xiao Zhu³, Jennette A Sakoff², Adam McCluskey¹

¹ The University of Newcastle, Chemistry, Newcastle, Australia

² Calvary Mater Hospital, Medical Oncology, Newcastle, Australia

³ Purdue University, Chemistry, West Lafayette, United States

View abstract

Combining C-H functionalisation and flow photochemical heterocyclic metamorphosis (FP-HM) for the synthesis of benzo[1,3]oxazepines

Jasraj S. Babra, Andrew T. Russell, Christopher D. Smith, Yuxiong Zhang

Department of Chemistry, University of Reading, Whiteknights, Reading, RG6 6AD, UK

View abstract

Photochemical Synthesis of Heterocycles: Merging Flow Processing and Metal-Catalyzed Visible Light Photoredox Transformations

T Glasnov

Institute of Chemistry, University of Graz, Graz, Austria

View abstract

Photoredox Iridium–Nickel Dual-Catalyzed Decarboxylative Arylation Cross-Coupling: From Batch to Continuous Flow via Self-Optimizing Segmented Flow Reactor

Hsiao-Wu Hsieh^†, Connor W. Coley^‡, Lorenz M. Baumgartner^‡, Klavs F. Jensen^*‡, Richard I. Robinson^*†

^† Global Discovery Chemistry − Chemical Technology Group, Novartis Institutes for Biomedical Research, 250 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States

^‡ Department of Chemical Engineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States

View abstract

Generation of Diversity Sets with High sp3 Fraction Using the Photoredox Coupling of Organotrifluoroborates and Organosilicates with Heteroaryl/Aryl Bromides in Continuous Flow

Kevin D Raynor, Gregory D May, Upul K. Bandarage, and Michael J. Boyd

Vertex Pharmaceuticals Inc., 50 Nothern Avenue, Boston, Massachusetts 02210, United States

View abstract

Exploring effects of intermittent light upon visible light promoted water oxidations

Dominic Walsh^*a, Pascaline Patureau^a, Karen Robertson^a, Shaun Reeksting^b, Anneke Lubben^b, Salvador Eslava^c, Mark T. Wellera^a

^a Department of Chemistry, University of Bath, Bath, BA2 7AY, UK. E-mail: [email protected]

^b Chemical Characterization and Analysis Facility, University of Bath, Bath, BA2 7AY, UK

^c Department of Chemical Engineering, University of Bath, BA2 7AY, UK

View abstract

A nanoporous graphene analog for superfast heavy metal removal and continuous-flow visible-light photoredox catalysis

Ran Xiao^a, John Michael Tobin^b, Meiqin Zha^a, Yunlong Hou^a, Jun He^c, Filipe Vilela^*b, Zhengtao Xu^*a

^a Department of Chemistry, City University of Hong Kong, 83 Tat Chee Avenue, Kowloon, Hong Kong

^b School of Engineering and Physical Sciences, Heriot-Watt University, Edinburgh, UK

^c School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China

View abstract

Visible-light-induced trifluoromethylation of highly functionalized arenes and heteroarenes in continuous flow

Irini Abdiaj^a, Cecilia Bottecchia^b, Jesus Alcazar^*a, Timothy Noёl^*b

^a Janssen Research & Development, Jarama 75A, 45007 Toledo, Spain

^b Department of Chemical Engineering and Chemistry, Micro Flow Chemistry & Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ Eindhoven, The Netherlands

View abstract

Singlet oxygen oxidations in homogeneous continuous flow using a gas–liquid membrane reactor

Antonia Kouridaki, Kevin Huvaere

EcoSynth NV, Industrielaan 12, 9800 Deinze, Belgium

View abstract

High throughput photo-oxidations in a packed bed reactor system

Caleb J. Kong, Daniel Fisher, Bimbisar K. Desai,. Yuan Yang, Saeed Ahmad, Katherine Belecki, B. Frank Gupton

Department of Chemistry and Department of Chemical and Life Science Engineering, Virginia Commonwealth University, 601 W. Main St. Richmond, VA 23220, USA

View abstract

Polymer-supported photosensitizers for oxidative organic transformations in flow and under visible light irradiation

John M. Tobin^†, Timothy J. D. McCabe^‡, Andrew W. Prentice^†, Sarah Holzer^†, Gareth O. Lloyd^†, Martin J. Paterson^†, Valeria Arrighi^†, Peter A. G. Cormack^‡, Filipe Vilela^†

^† School of Engineering and Physical Sciences, Heriot-Watt University, Edinburgh, EH14 4AS Scotland, United Kingdom

^‡ WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Thomas Graham Building, 295 Cathedral Street, Glasgow, G1 1XL Scotland, United Kingdom

View abstract

Continuous Flow α-Arylation of N,N-Dialkylhydrazones under Visible-Light Photoredox Catalysis

Juan A. Vega, José Manuel Alonso, Gabriela Méndez, Myriam Ciordia, Francisca Delgado, Andrés A. Trabanco

Neuroscience Medicinal Chemistry, Janssen Research & Development, Jarama 75A, 45007 Toledo, Spain

View abstract

Active Site-Mapping of Xylan-Deconstructing Enzymes with Arabinoxylan Oligosaccharides Produced by Automated Glycan Assembly

Deborah Senf, Colin Ruprecht, Goswinus de Kruijff, Sebastian Simonetti, Frank Schuhmacher, Peter Seeberger, Fabian Pfrengle

Max-Planck-Institute of Colloids and Interfaces, Biomolecular Systems, Potsdam, Germany

View abstract

Mixed-Linkage Glucan Oligosaccharides Produced by Automated Glycan Assembly Serve as Tools to Determine the Substrate Specificity of Lichenase

Pietro Dallabernardina, Frank Schuhmacher, Peter H Seeberger, Fabian Pfrengle

Max-Planck-Institute of Colloids and Interfaces, Biomolecular Systems, Potsdam, Germany

View abstract

Improving the throughput of batch photochemical reactions using flow: Dual photoredox and nickel catalysis in flow for C(sp2) C(sp3) cross-coupling

Irini Abdiaj, Jesús Alcázar

Janssen Research and Development, Janssen-Cilag, S.A., C/Jarama 75, 45007 Toledo, Spain

View abstract

Synthesis of Cycloalkyl Substituted 7-Azaindoles via Photoredox Nickel Dual Catalytic Cross-Coupling in Batch and Continuous Flow

Natalie Palaychuk, Travis J. DeLano, Michael J. Boyd, Jeremy Green, and Upul K. Bandarage

Vertex Pharmaceuticals Incorporated, 50 Northern Avenue, Boston, Massachusetts 02210, United States

View abstract

Acridinium-Based Photocatalysts: A Sustainable Option in Photoredox Catalysis

Amruta Joshi-Pangu^†, François Lévesque^†, Hudson G. Roth^‡, Steven F. Oliver^†, Louis-Charles Campeau^†, David Nicewicz^‡, Daniel A. DiRocco^†

^† Process Research & Development, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, United States

^‡ Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States

View abstract

Application of the Photoredox Coupling of Trifluoroborates and Aryl Bromides to Analog Generation Using Continuous Flow

Travis J. DeLano, Upul K. Bandarage, Natalie Palaychuk, Jeremy Green, and Michael J. Boyd

Vertex Pharmaceuticals Incorporated, 50 Northern Avenue, Boston, Massachusetts 02210, United States

View abstract

Expedited access to thieno[3,2-c]quinolin-4(5H)-ones and benzo[h]-1,6-naphthyridin-5(6H)-ones via a continuous flow photocyclization method

Y. Fang^a, G. K. Tranmer^*ab

^* Corresponding author

^a College of Pharmacy, Faculty of Health Science, University of Manitoba, Winnipeg, Canada

^b Department of Chemistry, Faculty of Science, University of Manitoba, Winnipeg, Canada

View abstract

BODIPY-based conjugated microporous polymers as reusable heterogeneous photosensitisers in a photochemical flow reactor

J. M. Tobin^a, J. Liu^b, H. Hayes^a, M. Demleitner^a, D. Ellis^a, V. Arrighi^a, Z. Xu^*b, F. Vilela^*a

^* Corresponding author

^a School of Engineering and Physical Sciences, Heriot-Watt University, Edinburgh, UK

^b Department of Biology and Chemistry, City University of Hong Kong, 83 Tat Chee Avenue, Kowloon, China

View abstract

Visible light activation of Boronic Esters enables efficient photoredox C(sp2)–C(sp3) cross-couplings in flow

Fabio Lima^a, Dr. Mikhail A. Kabeshov^a, Dr. Duc N. Tran^a, Dr. Claudio Battilocchio^a, Dr. Joerg Sedelmeier^b, Dr. Gottfried Sedelmeier^b, Dr. Berthold Schenkel^b, S. V. Ley^*a

^* Corresponding author

^a Department of Chemistry, University of Cambridge, Cambridge, UK

^b Novartis Pharma AG, Basel, Switzerland

View abstract

A laboratory-scale continuous flow chlorine generator for organic synthesis

Franz J. Strauss^a, David Cantillo^*ab, Javier Guerra^c, C. Oliver Kappe^*ab

^* Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, Graz, Austria

^a Research Center Pharmaceutical Engineering GmbH (RCPE), Inffeldgasse 13, 8010 Graz, Austria

^b Crystal Pharma, Gadea Pharmaceutical Group, A Division of AMRI, Parque Tecnológico de Boecillo, Valladolid, Spain

View abstract

Aryl amination using ligand-free Ni(II) salts and photoredox catalysis

Emily B. Corcoran¹, Michael T. Pirnot², Shishi Lin³, Spencer D. Dreher³, Daniel A. DiRocco³, Ian W. Davies³, Stephen L. Buchwald^2,*, David W. C. MacMillan^1,*

¹ Merck Center for Catalysis at Princeton University, Princeton, NJ 08544, USA

² Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA

³ Department of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065, USA

View abstract

Metal-free borylation of electron-rich aryl(pseudo)halides under continuous-flow photolytic conditions

Kai Chen^a, Man Sing Cheung^b, Zhenyang Lin^*b, Pengfei Li^*a

^a Center for Organic Chemistry, Frontier Institute of Science and Technology (FIST) and Frontier Institute of Chemistry, Xi'an Jiaotong University, 99 Yanxiang Road, Xi'an, China

^b Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, China

View abstract

A scalable and operationally simple radical trifluoromethylation

Joel W. Beatty¹, James J. Douglas^1,2, Kevin P. Cole², Corey R. J. Stephenson¹

¹ Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA

² Small Molecule Design and Development, Lilly Research Laboratoires, Eli Lilly and Company, Indianapolis, Indiana 46285, USA

View abstract

Photoactive and metal-free polyamide-based polymers for water and wastewater treatment under visible light irradiation

Junjie Shen^a, Roman Steinbach^a, John Tobin^a, Mayumi Mouro Nakata^a, Matthew Bower^b, Martin McCoustra^a, Helen Bridle^a, Valeria Arrighi^a, Filipe Vilela^a

^a School of Engineering and Physical Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, United Kingdom

^b Drinking Water Quality Regulator for Scotland, Edinburgh, EH6 6WW, United Kingdom

View abstract

Continuous flow photo-initiated RAFT polymerisation using a tubular photochemical reactor

James Gardiner ^a, Christian H. Hornung ^a, John Tsanaktsidis ^a, Duncan Guthrie ^b

^a CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia

^b Vapourtec Ltd, Park Farm Business Centre, Bury St Edmunds IP28 6TS, United Kingdom

View abstract

Continuous-flow photochemistry: a need for chemical engineering

Karine Loubière ^a,b, Michael Oelgemöller ^c, Tristan Aillet ^a,b, Odile Dechy-Cabaret ^a,d, Laurent Prat ^a,b

^a CNRS, Laboratoire de Génie Chimique (LGC UMR 5503), 4 allée Emile Monso, BP 84234, 31432 Toulouse, France

^b Université de Toulouse, INPT, ENSIACET, F-31432 Toulouse, France

^c James Cook University, College of Science, Technology and Engineering, Townsville, Queensland 4811, Australia

^d CNRS, Laboratoire de Chimie de Coordination (LCC UPR 8241), 205 route de Narbonne, BP 44099, F-31077 Toulouse, France

View abstract

Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions

Kai Chen, Shuai Zhang, Pei He, Pengfei Li ^*

Center for Organic Chemistry, Frontier Institute of Science and Technology (FIST), Xi'an Jiaotong University, 99 Yanxiang Road, Xi'an, Shaanxi 710054, China

View abstract

Continuous flow photochemistry as an enabling synthetic technology: synthesis of substituted-6(5H)-phenanthridinones for use as poly(ADP-ribose) polymerase inhibitors

Y. Fang ^a, G. K. Tranmer ^*a,b

^* Corresponding authors ^a College of Pharmacy, Faculty of Health Sciences, University of Manitoba, Winnipeg, Canada

^b Department of Chemistry, Faculty of Science, University of Manitoba, Winnipeg, Canada

View abstract

Visible-light photoredox catalysis using a macromolecular ruthenium complex: reactivity and recovery by size-exclusion nanofiltration in continuous flow

Javier Guerra ^ab, David Cantillo ^a, C. Oliver Kappe ^*a, Antonio Macchiarulo ^a, Antimo Gioiello ^*a

^a Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, A-8010 Graz, Austria

^b Crystal Pharma, Gadea Pharmaceutical Group, a division of AMRI, Parque Tecnológico de Boecillo, Valladolid, 47151, Spain

View abstract

Continuous photochemistry: the flow synthesis of ibuprofen via a photo-Favorskii rearrangement

M. Baumann^a, Ian R. Baxendale^{* a}

^a Department of Chemistry, University of Durham, South Road, Durham, UK

View abstract

Automated glycan assembly of xyloglucan oligosaccharides

Pietro Dallabernardina^{a b}, Frank Schuhmacher^{a b}, Peter H. Seeberger^{a b}, Fabian Pfrengle^{* a b}

^a Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany

^b Freie Universität Berlin, Institute of Chemistry and Biochemistry, Arnimallee 22, 14195 Berlin, Germany

View abstract

Photodecarboxylations in an advanced meso-scale continuous flow photoreactor

Sam Josland¹, Saira Mumtaz², Michael Oelgemöller^{2 *}

¹ University of Southampton, Department of Chemistry, University Road, Southampton, SO17 1BJ, United Kingdom

² James Cook University, College of Science, Technology and Engineering, Townsville, QLD 4811, Australia

View abstract

Photodecarboxylative Benzylations of N-Methoxyphthalimide under Batch and Continuous-Flow Conditions

Hossein Mohammadkhani Pordanjani ^A ^B, Christian Faderl ^A ^C, Jun Wang ^A, Cherie A. Motti ^D, Peter C. Junk ^A, Michael Oelgemöller ^A ^E

^A James Cook University, College of Science, Technology and Engineering, Townsville, Qld 4811, Australia.

^B Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran.

^C Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, D-93053 Regensburg, Germany.

^D Australian Institute of Marine Science (AIMS), Biomolecular Analysis Facility, Townsville, Qld 4810, Australia.

^E Corresponding author. Email: [email protected]

View abstract

Light-Induced C-H Arylation of (Hetero)arenes by In Situ Generated Diazo Anhydrides

Dr. David Cantillo¹, Dr. Carlos Mateos², Dr. Juan A. Rincon², Dr. Oscar de Frutos^{2 *}, Prof. Dr. C. Oliver Kappe^{1 *}

¹ Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, 8010 Graz (Austria)

² Centro de Investigación Lilly S. A. Avda. de la Industria 30, 28108 Alcobendas-Madrid (Spain)

View abstract

Factors Influencing the Regioselectivity of the Oxidation of Asymmetric Secondary Amines with Singlet Oxygen

Dr. Dmitry B. Ushakov ^{1 †}, Matthew B. Plutschack ^{1 †}, Dr. Kerry Gilmore ^{1 *}, Prof. Dr. Peter H. Seeberger ¹

¹ Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam (Germany)

View abstract

Electroactive and Photoactive Poly[Isoindigo-alt-EDOT] Synthesized Using Direct (Hetero)Arylation Polymerization in Batch and in Continuous Flow

François Grenier ^†, Badrou Réda Aïch ^{† ‡}, Yu-Ying Lai ^§, Maxime Guérette ^†, Andrew B. Holmes ^§, Ye Tao ^‡, Wallace W. H. Wong ^{* §}, Mario Leclerc ^{* †}

^† Département de Chimie, Université Laval, Québec City, Qc G1V 0A6, Canada

^‡ Information and Communications Technologies Portfolio, National Research Council of Canada, Ottawa, ON K1A 0R6, Canada

^§ School of Chemistry, Bio21 Institute, the University of Melbourne, 30 Flemington Road, Parkville, Victoria 3010, Australia

View abstract

Reevaluation of the 2-nitrobenzyl protecting group for nitrogen containing compounds: an application of flow photochemistry

Chloe I. Wendell, Michael J. Boyd

Vertex Pharmaceuticals Inc., 50 Northern Avenue, Boston, MA, United States

View abstract

Consecutive Oxygen-based Oxidations Convert Amines to a-Cyanoepoxides

Dmitry B. Ushakov^a, Kerry Gilmore^*a, Peter H. Seeberger^*a,b

^aMax Planck Institute of Colloids and Interfaces, Potsdam, Germany

^bInstitute of Chemistry and Biochemistry, Freie Universität Berlin, Berlin, Germany

View abstract

Synthesis of a Carprofen Analogue Using a Continuous Flow UV-Reactor

Antoine Caron, Augusto C. Hernandez-Perez, Shawn K. Collins^*

Department of Chemistry and Centre for Green Chemistry and Catalysis, Université de Montréal, Québec, Canada.

View abstract

Continuous Synthesis of Artemisinin-Derived Medicines

Kerry Gilmore^a, Daniel Kopetzki^a, Ju Weon Lee^b, Zoltan Horvath^b, D. Tyler McQuade^a, Andreas Seidel-Morgenstern^b,c, Peter H. Seeberger^a,d

^aMax-Planck-Institute of Colloids and Interfaces, Department of Biomolecular Systems, Germany

^bMax-Planck-Institute for Dynamics of Complex Technical Systems, Germany

^cOtto-von-Guericke-University, Chair for Chemical Process Technology, Germany

^dFreie Universität Berlin, Institute of Chemistry and Biochemistry, Berlin, Germany

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Continuous-Flow Oxidative Cyanation of Primary and Secondary Amines Using Singlet Oxygen

Dmitry B. Ushakov, Kerry Gilmore, Daniel Kopetzki, D. Tyler McQuade, Peter H. Seeberger

¹Department für Biomolekulare Systeme, Max-Planck-Institut für Kolloid- und Grenzflächenforschung, Potsdam, Germany

²Institut für Chemie und Biochemie, Freie Universität Berlin, Berlin, Germany

³Department of Chemistry and Biochemistry, Florida State University, Tallahassee, USA

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Synthesis of Carbohydrate-Functionalised Sequence-Defined Oligo(amidoamine)s by Photochemical ThiolEne Coupling in a Continuous Flow Reactor

Felix Wojcik^1,2, Alexander G. O'Brien^1,2, Sebastian Götze^1,2, Peter H. Seeberger^1,2, Laura Hartmann^1,2

¹Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Potsdam (Germany)

²Institute for Chemistry and Biochemistry, Freie Universität Berlin, Berlin (Germany)

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Visible Light-Initiated Preparation of Functionalized Polystyrene Monoliths for Flow Chemistry

Farhan R. Bou-Hamdan¹, Kathleen Krüger¹, Klaus Tauer¹, Tyler McQuade^1,3 , Peter H. Seeberger ^1,2

¹Max Planck Institute of Colloids and Interfaces Potsdam, Germany.

²Institute of Chemistry and Biochemistry, Freie Universität Berlin , Germany.

³Department of Chemistry and Biochemistry, Florida State University, USA.

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Continuous-Flow Synthesis of the Anti-Malaria Drug Artemisinin

François Lévesque¹, Peter H. Seeberger^1,2

¹Department for Biomolecular Systems, Max-Planck Institute for Colloids and Interfaces, Germany

²Institute for Chemistry and Biochemistry, Freie Universität Berlin, Germany

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Continuous flow photolysis of aryl azides: Preparation of 3H-azepinones

Farhan R. Bou-Hamdan, François Lévesque, Alexander G. O'Brien, Peter H. Seeberger

Max Planck Institute of Colloids and Interfaces, Berlin, Germany

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Application Notes regarding Photoexcitation reactions and the applications of the Vapourtec UV-150 reactor

Application Note 71: Photochemistry – Process development and scale up to kilos / day

This application note demonstrates a 385 % increase in throughput in the ene-like reaction of singlet oxygen with citronellol, by increasing the photon molar output. By using Vapourtec’s UV-150 photochemical reactor equipped with a 420 nm High Power LED, a throughput of 59 g/h (1.4 kg/day or over half a tonne a year) can be achieved.

This application note demonstrates a 230 % increase in throughput on the direct [2+2] cycloaddition of maleic anhydride with ethene to form a cyclobutane motif by using the new Vapourtec’s 365 nm High Power LED.

Application-note-62-low-pressure-mercury-photochemistry

After the Ley group, of the University of Cambridge, published a fascinating method of generating nonstabilised diazo compounds using a photochemical method,1,2 the team at New Path Molecular Research have applied the method to increase the product throughput of the synthesis of a pharmaceutical intermediate, using a newly developed high-power low-pressure mercury lamp.

This application note describes:

The use of a 28 W low-pressure mercury
lamp at 310 nm
The effective, 3-fold increase in product
throughput of a pharmaceutical
intermediate

A Vapourtec E-Series with V-3 Pumps and the UV-150 Photochemical Reactor

In this application note, we demonstrate how to safely use solutions of bromine under a wide range of reaction conditions. This is achieved with the versatility of the Vapourtec E-series, V-3 pumps and our UV-150 photochemical reactor.

This application describes:

Safe and easy pumping of an elemental bromine solution
Effective and repeatable photobromination in a UV-150 photochemical reactor
Rapid scale-up to over 10 g/hr

Safer Handling of Bromine

Elemental bromine is an efficient reagent for incorporating bromine into a range of benzyl, allylic and heterocyclic bromomethyl compounds but can present a hazard for handling in the laboratory. The resultant bromomethyl benzenes are often toxic and lachrymatory, and careful handling to avoid exposure is needed. Using the E-Series and UV-150 photochemical reactor it has been possible to carry out a range of photochemical brominations without needing to handle bromine, beyond making a stock solution.

Improved reaction rates

In the chemical literature, we found an example that required a significantly longer reaction time than any other example in the paper. Using the E-Series and UV-150 photochemical reactor, we have been able to reduce the reaction time from 7.5 minutes to 1 minute, with improved reaction yields (from 69% to 89%).

In our application note 59 we found an unexpected photohydration taking place, instead of a cycloaddition during a photochemical library synthesis of [2+2] cycloadducts. Investigating further, we learned that it has not been reported in continuous flow in the literature before. We decided to explore this reaction further in this application note, which describes:

– Efficient and clean functionalisation of a candidate for an anti-cancer pharmaceutical

– New reaction for continuous flow

– Rapid investigation of reaction conditions, enabling double the throughput

– Optimisation of a photochemical reaction

– Throughput of 0.67 g/hr from a photochemical reaction

– Isolated yield of 80% with 99% purity

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