Continuous Microflow [2 + 2] Photocycloaddition Reactions Using Energy-saving Compact Light Sources

Photocycloaddition of cyclohexenones with vinyl acetates or vinyl ethers, and the Paterno-Büchi reaction were carried out using photomicroreactors in combination with compact light sources such as low-power black lights and UV LEDs. The observed high efficiency holds promise as an energy-saving protocol for photoinduced [2 + 2] cycloaddition reactions.

[1]  Takehiko Kitamori,et al.  Photocatalytic redox-combined synthesis of l-pipecolinic acid with a titania-modified microchannel chip , 2005 .

[2]  Hajime Maeda,et al.  Intramolecular Photocycloaddition of 2-(2-Alkenyloxymethyl)naphthalene-1-carbonitriles Using Glass-Made Microreactors , 2007 .

[3]  Masaaki Sato,et al.  Continuous microflow synthesis of butyl cinnamate by a Mizoroki-Heck reaction using a low-viscosity ionic liquid as the recycling reaction medium , 2004 .

[4]  Jun-ichi Yoshida,et al.  Flash chemistry: fast chemical synthesis by using microreactors. , 2008, Chemistry.

[5]  Atsushi Sugimoto,et al.  An automated-flow microreactor system for quick optimization and production: application of 10- and 100-gram order productions of a matrix metalloproteinase inhibitor using a Sonogashira coupling reaction , 2009 .

[6]  T. Fukuyama,et al.  A copper-free Sonogashira coupling reaction in ionic liquids and its application to a microflow system for efficient catalyst recycling. , 2002, Organic Letters.

[7]  Tadashi Suzuki,et al.  N-Alkylation of amines by photocatalytic reaction in a microreaction system , 2008 .

[8]  Norbert Kockmann,et al.  Micro Process Engineering , 2006 .

[9]  K. Jensen,et al.  Photochemical reactions and on-line UV detection in microfabricated reactors. , 2001, Lab on a chip.

[10]  Peter H Seeberger,et al.  Microreactors as tools for synthetic chemists-the chemists' round-bottomed flask of the 21st century? , 2006, Chemistry.

[11]  M. Crimmins Synthetic Applications of Intramolecular Enone-Olefin Photocycloadditions , 1988 .

[12]  Volker Hessel,et al.  Chemical micro process engineering , 2003 .

[13]  Jun-ichi Yoshida,et al.  Flash chemistry: flow microreactor synthesis based on high-resolution reaction time control. , 2010, Chemical record.

[14]  H. Löwe,et al.  Chemistry in microstructured reactors. , 2004, Angewandte Chemie.

[15]  H. Girault,et al.  Monolithic and flexible polyimide film microreactors for organic microchemical applications fabricated by laser ablation. , 2010, Angewandte Chemie.

[16]  S. Schreiber,et al.  The Paterno–Büchi Reaction , 1991 .

[17]  T. Fukuyama,et al.  Adventures in Inner Space: Microflow Systems for Practical Organic Synthesis , 2008 .

[18]  Yanju Wang,et al.  Integrated Microfluidic Reactors. , 2009, Nano today.

[19]  T. Fukuyama,et al.  Diastereoselective [2 + 2] Photocycloaddition of Chiral Cyclic Enone and Cyclopentene Using a Microflow Reactor System , 2010 .

[20]  Robert C. R. Wootton,et al.  A Microfabricated Nanoreactor for Safe, Continuous Generation and Use of Singlet Oxygen , 2002 .

[21]  K. Mizuno,et al.  Enhanced Efficiency and Regioselectivity of Intramolecular (2π + 2π) Photocycloaddition of 1-Cyanonaphthalene Derivative Using Microreactors , 2005 .

[22]  Teijiro Ichimura,et al.  Photocatalytic Reduction in Microreactors , 2006 .

[23]  Andreas Kirschning,et al.  Continuous flow techniques in organic synthesis. , 2003, Chemistry.

[24]  Takahide Fukuyama,et al.  Spurring radical reactions of organic halides with tin hydride and TTMSS using microreactors. , 2008, Organic letters.

[25]  Atsushi Sugimoto,et al.  Microflow photo-radical reaction using a compact light source: application to the Barton reaction leading to a key intermediate for myriceric acid A , 2009 .

[26]  Wolfgang Ehrfeld,et al.  Microreactors: New Technology for Modern Chemistry , 2000 .

[27]  Atsushi Sugimoto,et al.  The Barton reaction using a microreactor and black light. Continuous-flow synthesis of a key steroid intermediate for an endothelin receptor antagonist , 2006 .

[28]  N. Ohba,et al.  Photocatalytic N-alkylation of benzylamine in microreactors , 2007 .

[29]  I. Ryu,et al.  Microflow photo-radical chlorination of cycloalkanes , 2011 .

[30]  Timothy F. Jamison,et al.  Continuous flow multi-step organic synthesis , 2010 .

[31]  Jeremy L. Steinbacher,et al.  Greener approaches to organic synthesis using microreactor technology. , 2007, Chemical reviews.

[32]  Michael Oelgemöller,et al.  Micro-photochemistry: photochemistry in microstructured reactors. The new photochemistry of the future? , 2008, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[33]  T. Fukuyama,et al.  Addition of allyl bromide to phenylacetylene catalyzed by palladium on alumina and its application to a continuous flow synthesis , 2009 .

[34]  T. Wirth,et al.  Advanced organic synthesis using microreactor technology. , 2007, Organic & biomolecular chemistry.

[35]  T. Fukuyama,et al.  Microflow radical carboaminoxylations with a novel alkoxyamine. , 2009, Organic letters.

[36]  N. R. Hunter,et al.  Cyclobutanes in organic synthesis. Part I. Fragmentation to 1,4-dicarbonyl compounds. General considerations , 1970 .

[37]  J. Winkler,et al.  2 + 2 PHOTOCYCLOADDITION/FRAGMENTATION STRATEGIES FOR THE SYNTHESIS OF NATURAL AND UNNATURAL PRODUCTS , 1995 .

[38]  T. Fukuyama,et al.  Quick Execution of [2+2] Type Photochemical Cycloaddition Reaction by Continuous Flow System Using a Glass-made Microreactor , 2004 .

[39]  David Linke,et al.  Application of microstructured reactor technology for the photochemical chlorination of alkylaromatics , 2002 .

[40]  Klavs F Jensen,et al.  Integrated microreactors for reaction automation: new approaches to reaction development. , 2010, Annual review of analytical chemistry.

[41]  Jun-ichi Yoshida,et al.  Photodimerization of Maleic Anhydride in a Microreactor Without Clogging , 2010 .

[42]  K. Nolan,et al.  From conventional to microphotochemistry: photodecarboxylation reactions involving phthalimides. , 2010, Organic letters.

[43]  Kosei Ueno,et al.  Photocyanation of pyrene across an oil/water interface in a polymer microchannel chip. , 2002, Lab on a chip.

[44]  K. Mizuno,et al.  One-step synthesis of benzotetra- and benzopentacyclic compounds through intramolecular [2+3] photocycloaddition of alkenes to naphthalene. , 2006, Angewandte Chemie.

[45]  T. Wirth,et al.  Microreactors in organic synthesis and catalysis , 2008 .

[46]  M. D’Auria Paternò–Büchi Reaction , 2012 .

[47]  Mark Pickworth,et al.  A practical flow reactor for continuous organic photochemistry. , 2005, The Journal of organic chemistry.

[48]  Paul Watts,et al.  Recent advances in synthetic micro reaction technology. , 2007, Chemical communications.

[49]  N. Hoffmann,et al.  Photochemical reactions as key steps in organic synthesis. , 2008, Chemical reviews.

[50]  K. Nolan,et al.  Photosensitized addition of isopropanol to furanones in a 365 nm UV-LED microchip , 2010, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[51]  Masaaki Sato,et al.  Low pressure Pd-catalyzed carbonylation in an ionic liquid using a multiphase microflow system. , 2006, Chemical communications.

[52]  T. Fukuyama,et al.  Radical carbonylations using a continuous microflow system , 2009, Beilstein journal of organic chemistry.

[53]  Hsing‐Jang Liu,et al.  Synthetic application of cyclobutanes V. α-Carbalkoxymethylation of α, β-unsaturated ketones , 1977 .

[54]  E. Corey,et al.  A Study of the Photochemical Reactions of 2-Cyclohexenones with Substituted Olefins , 1964 .

[55]  Toshiaki Murata,et al.  Recent progress on photoreactions in microreactors , 2007 .

[56]  P. Song,et al.  CRC handbook of organic photochemistry and photobiology , 2004 .

[57]  Volker Hessel,et al.  Micro process engineering : a comprehensive handbook , 2009 .