Photochemical Reactions and the Vapourtec UV-150 Photochemical Reactor

    Photochemistry 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 Photochemistry 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 Photochemical 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 photochemistry 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 photochemical 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

    Examples of published literature for Photochemical Reactions and the Vapourtec UV-150 Photochemical Reactor

    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. Wonga, J. M. Tobinb, Z. Xua, 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. Mortzfelda,b, Jörg Pietruszkab, 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 Weia, Irini Abdiajb, Carlo Sambiagioa, Chenfei Lic, Eli Zysman-Colmanc, Jesús Alcázarb, Timothy Noëla

    • 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 Zhakeyevac, John Tobina, Huizhi Wangb, Filipe Vilelaa, Jin Xuanac

    • 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 Konrad1,2, Christian Fengler1,2, Sarrah Putwa1, and Christopher Barner-Kowollik1,2

    • 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. Williamsa,b, Yuma Otakea, Guilhem Coussanesc, Iakovos Saridakiscc, Nuno Maulidecc, C. Oliver Kappeaa,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 Huntera, Sam Joslanda, Joseph Mooreb, Duncan Guthrieb, Mark J. Robertsona, Michael Oelgemöllera

    • 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. Heightmana, Steven V. Leyb, Fabio Limab,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 Chena, b, Oscar de Frutosc, Carlos Mateosc, Juan A. Rinconc, 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 Radjagobalouab, Jean-François Blancoa, Odile Dechy-Cabaretb, Michael Oelgemöllerc, Karine Loubièrea

    • 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 Transformati

    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 Patureaua, Karen Robertsona, Shaun Reekstingb, Anneke Lubbenb, Salvador Eslavac, Mark T. Welleraa

    • a Department of Chemistry, University of Bath, Bath, BA2 7AY, UK. E-mail: d.walsh2@bath.ac.uk
    • 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 Xiaoa, John Michael Tobinb, Meiqin Zhaa, Yunlong Houa, Jun Hec, 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 Abdiaja, Cecilia Bottecchiab, 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. Fanga, 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. Tobina, J. Liub, H. Hayesa, M. Demleitnera, D. Ellisa, V. Arrighia, 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 Limaa, Dr. Mikhail A. Kabeshova, Dr. Duc N. Trana, Dr. Claudio Battilocchioa, Dr. Joerg Sedelmeierb, Dr. Gottfried Sedelmeierb, Dr. Berthold Schenkelb, 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. Straussa, David Cantillo*ab, Javier Guerrac, 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. Buchwald2,*, David W. C. MacMillan1,*

    • 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 Chena, Man Sing Cheungb, 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. Douglas1,2, 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 Shena, Roman Steinbacha, John Tobina, Mayumi Mouro Nakataa, Matthew Bowerb, Martin McCoustraa, Helen Bridlea, Valeria Arrighia, Filipe Vilelaa

    • 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. Baumanna, Ian R. Baxendale* a

    • a Department of Chemistry, University of Durham, South Road, Durham, UK
    View abstract

    Automated glycan assembly of xyloglucan oligosaccharides

    Pietro Dallabernardinaa b, Frank Schuhmachera b, Peter H. Seebergera 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 Oelgemöller2 *

    • 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: michael.oelgemoeller@jcu.edu.au
    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 Frutos2 *, Prof. Dr. C. Oliver Kappe1 *

    • 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. Ushakova, 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 Gilmorea, Daniel Kopetzkia, Ju Weon Leeb, Zoltan Horvathb, D. Tyler McQuadea, Andreas Seidel-Morgensternb,c, Peter H. Seebergera,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
    View abstract

    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
    View abstract

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

    Felix Wojcik1,2, Alexander G. O'Brien1,2, Sebastian Götze1,2, Peter H. Seeberger1,2, Laura Hartmann1,2

    • 1Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Potsdam (Germany)
    • 2Institute for Chemistry and Biochemistry, Freie Universität Berlin, Berlin (Germany)
    View abstract

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

    Farhan R. Bou-Hamdan1, Kathleen Krüger1, Klaus Tauer1, Tyler McQuade1,3 , 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.
    View abstract

    Continuous-Flow Synthesis of the Anti-Malaria Drug Artemisinin

    François Lévesque1, Peter H. Seeberger1,2

    • 1Department for Biomolecular Systems, Max-Planck Institute for Colloids and Interfaces, Germany
    • 2Institute for Chemistry and Biochemistry, Freie Universität Berlin, Germany
    View abstract

    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
    View abstract

    Application Notes regarding Photochemical Reactions and the Vapourtec UV-150 Photochemical Reactor

    Application Note 66: 230% increase in throughput of a photocycloaddition demonstrated by Vapourtec High Power LED.

    high-power-led-vapourtec-E-Series

    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.

    Read more

    Application Note 62: Synthesis of pharmaceutical intermediate by cross-coupling with non-stabilised diazo compounds

    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
    Read more

    Application Note 61: Photochemical bromination with elemental bromine in continuous flow

    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%).

    Read more

    Application Note 60: Photochemical hydration and scale-up of an anti-cancer candidate

    Dichroic-mirror

    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

    Read more

    Application Note 59 – Automated photochemical library synthesis

    Photochemical-Library-Synthesis

    A synthesis of a library of compounds enables the chemist to rapidly screen possible chemistries and produce small quantities to be used for other screening processes. This application note describes:

    • Rapid synthesis of a library of 12 [2+2] photo-cycloadducts in 50 mg quantities
    • Rapid screening of a range of photosensitisers
    • Optimisation and scale-up of two products to several grams scale
    Read more

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