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 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

    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

    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 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

    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 Chemistr
    • 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 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

    Application Note 58 – Visible light singlet oxygen

    Application note 58 Singlet Oxygen

    In this application, the conversion of α-terpinene to ascaridole was used to indirectly detect the formation of singlet oxygen in continuous flow. The production of singlet oxygen in continuous flow was optimised using the two methods, and the heterogeneous photocatalyst stability was investigated. Once optimised, the singlet oxygen was used for the aerobic oxidation of boronic acids to phenols, and to degrade two environmental pollutants: bis-phenol A and cimetidine.

    This application note describes:

    • Production of singlet oxygen in continuous flow
    • The use of the UV-150 photochemical reactor for heterogeneous dispersions
    • Use of heterogeneous photocatalysts as slurries and packed beds in continuous flow
    • Easy handling of a complex flow stream of solid, liquid and gas
    Read more

    Application Note 56 – Photodecarboxylative addition of phenylacetic acid to N-methyl phthalimide

    Reaction-Scheme

    This application note illustrates the use of the Vapourtec UV-150 photochemical reactor for the photodecarboxylative benzylation of N-methyl phthalimide. The transformation has been systematically optimized in terms of reagent concentration and residence time. The optimized procedure was subsequently performed on large-scale, achieving a productivity of 1.34 g (88%) of product per hour (or 32.16 g per day). The reactor enabled continuous photochemistry in an easy-to-use, safe and efficient manner.

    Read more

    Application Note 48 – Photochemical synthesis of Cubanes

    Application-Note-48-Photochemical-Synthesis-of-a-Cubane

    This application note demonstrates the preparation of cage compound 2 from an advanced diene precursor 1, which can be prepared from cyclopentanone. After optimization, this key photochemical [2+2] photocycloaddition was successfully scaled up to multigram scale, and the cycloadduct was transformed to 1,4-cubane dicarboxylate 3.

    Read more

    Application Note 47 – [2+2] Photocycloaddition with wavelength specific low pressure mercury lamps

    Application-Note-47-Photocycoladdition-using-low-pressure-mercury-lamps

    This application note uses the photochemical reaction explored in application note 36, the photocycloaddition of maleimide and 1-hexyne, to explore the performance of Vapourtec’s new low pressure mercury lamps. For this reaction the low pressure lamps are used in place of the
    medium pressure lamp with filters. Three low pressure mercury lamps are tested, each with a specific and very narrow wavelength emission band.

    Read more

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