Application of metal-based reagents and catalysts in microstructured flow devices.

Over the years, organic synthesis has witnessed several improvements through the development of new chemical transformations or more efficient reagents for known processes. Likewise, technological advances, aiming at speeding up reactions and facilitating their work-up, have established themselves in academic as well as in industrial laboratories. In this Minireview, we highlight very recent developments in flow chemistry, focusing on organometallic reagents and catalysts. First, we describe reactions with homogeneous catalysts immobilized on different support materials using the concept of packed bed reactors. In the last chapter, we will discuss applications that utilize organometallic reagents.

[1]  Ryan L. Hartman,et al.  Deciding whether to go with the flow: evaluating the merits of flow reactors for synthesis. , 2011, Angewandte Chemie.

[2]  Andreas Kirschning,et al.  Ten key issues in modern flow chemistry. , 2011, Chemical communications.

[3]  Jun-ichi Yoshida,et al.  A flow-microreactor approach to protecting-group-free synthesis using organolithium compounds. , 2011, Nature communications.

[4]  Jun-ichi Yoshida,et al.  Green and sustainable chemical synthesis using flow microreactors. , 2011, ChemSusChem.

[5]  J. Yoshida,et al.  Asymmetric carbolithiation of conjugated enynes: a flow microreactor enables the use of configurationally unstable intermediates before they epimerize. , 2011, Journal of the American Chemical Society.

[6]  Jonathan P. McMullen,et al.  Palladium-catalyzed amination reactions in flow: overcoming the challenges of clogging via acoustic irradiation , 2011 .

[7]  T. Wirth,et al.  Intelligent microflow: development of self-optimizing reaction systems. , 2011, Angewandte Chemie.

[8]  Jun-ichi Yoshida,et al.  Cross-coupling in a flow microreactor: space integration of lithiation and Murahashi coupling. , 2010, Angewandte Chemie.

[9]  Jun-ichi Yoshida,et al.  A flow microreactor system enables organolithium reactions without protecting alkoxycarbonyl groups. , 2010, Chemistry.

[10]  Klavs F Jensen,et al.  An integrated microreactor system for self-optimization of a Heck reaction: from micro- to mesoscale flow systems. , 2010, Angewandte Chemie.

[11]  Oliver Reiser,et al.  Nanoparticles as semi-heterogeneous catalyst supports. , 2010, Chemistry.

[12]  D. O’Shea,et al.  Automated generation and reactions of 3-hydroxymethylindoles in continuous-flow microreactors. , 2010, Chemistry.

[13]  Sankaranarayanapillai Shylesh,et al.  Magnetisch abtrennbare Nanokatalysatoren: Brücken zwischen homogener und heterogener Katalyse , 2010 .

[14]  S. Shylesh,et al.  Magnetically separable nanocatalysts: bridges between homogeneous and heterogeneous catalysis. , 2010, Angewandte Chemie.

[15]  Daniele Vigo,et al.  Reaction of Grignard reagents with carbonyl compounds under continuous flow conditions , 2010 .

[16]  Steven V Ley,et al.  The application of flow microreactors to the preparation of a family of casein kinase I inhibitors. , 2010, Organic & biomolecular chemistry.

[17]  W. Leitner,et al.  Continuous Enantioselective Hydrogenation with a Molecular Catalyst in Supported Ionic Liquid Phase under Supercritical CO2 Flow , 2010 .

[18]  Klavs F. Jensen,et al.  Aminolysis of Epoxides in a Microreactor System: A Continuous Flow Approach to β-Amino Alcohols , 2010 .

[19]  W. Stark,et al.  Cu(II)−Azabis(oxazoline) Complexes Immobilized on Magnetic Co/C Nanoparticles: Kinetic Resolution of 1,2-Diphenylethane-1,2-diol under Batch and Continuous-Flow Conditions , 2010 .

[20]  Steven V Ley,et al.  Multi-step synthesis by using modular flow reactors: the preparation of yne--ones and their use in heterocycle synthesis. , 2010, Chemistry.

[21]  Norbert Kockmann,et al.  Harsh Reaction Conditions in Continuous‐Flow Microreactors for Pharmaceutical Production , 2009 .

[22]  Volker Hessel,et al.  Novel Process Windows – Gate to Maximizing Process Intensification via Flow Chemistry , 2009 .

[23]  J. Rolland,et al.  Continuous flow enantioselective arylation of aldehydes with ArZnEt using triarylboroxins as the ultimate source of aryl groups , 2009, Beilstein journal of organic chemistry.

[24]  Zheng Wang,et al.  Development of a continuous-flow system for asymmetric hydrogenation using self-supported chiral catalysts. , 2009, Chemistry.

[25]  Peter H Seeberger,et al.  Asymmetric reactions in continuous flow , 2009, Beilstein journal of organic chemistry.

[26]  P. Seeberger,et al.  5‐(Pyrrolidin‐2‐yl)tetrazol‐katalysierte Aldol‐ und Mannich‐Reaktionen: schnellere Reaktionen und niedrigere Katalysatorbeladung in einem Durchflussreaktor , 2009 .

[27]  P. Seeberger,et al.  5-(Pyrrolidin-2-yl)tetrazole-catalyzed aldol and mannich reactions: acceleration and lower catalyst loading in a continuous-flow reactor. , 2009, Angewandte Chemie.

[28]  G. Rowlands,et al.  Enantiospecific synthesis of [2.2]paracyclophane-4-thiol and derivatives , 2009, Beilstein journal of organic chemistry.

[29]  C. Oliver Kappe,et al.  Continuous‐Flow Microreactor Chemistry under High‐Temperature/Pressure Conditions , 2009 .

[30]  Klavs F. Jensen,et al.  Supercritical Continuous‐Microflow Synthesis of Narrow Size Distribution Quantum Dots , 2008 .

[31]  S. Loebbecke,et al.  Use of immobilized organic base catalysts for continuous-flow fine chemical synthesis , 2008 .

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

[33]  J. Ying,et al.  Siliceous Mesocellular Foam‐Supported Aza(bisoxazoline)‐Copper Catalysts , 2008 .

[34]  R. Haag,et al.  Continuous Application of Polyglycerol‐Supported Salen in a Membrane Reactor: Asymmetric Epoxidation of 6‐Cyano‐2,2‐dimethylchromene , 2008 .

[35]  C. Wiles,et al.  Continuous Flow Reactors, a Tool for the Modern Synthetic Chemist , 2008 .

[36]  P. Seeberger,et al.  Trimethylaluminium mediated amide bond formation in a continuous flow microreactor as key to the synthesis of rimonabant and efaproxiral. , 2008, Chemical communications.

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

[38]  Klavs F Jensen,et al.  Accelerating reactions with microreactors at elevated temperatures and pressures: profiling aminocarbonylation reactions. , 2007, Angewandte Chemie.

[39]  Paul Watts,et al.  Micro reactors: a new tool for the synthetic chemist. , 2007, Organic & biomolecular chemistry.

[40]  C. Oliver Kappe,et al.  Microwave‐Assisted Synthesis under Continuous‐Flow Conditions , 2007 .

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

[42]  F. Fülöp,et al.  Continuous enantioselective hydrogenation of activated ketones on a pt-cd chiral catalyst: use of h-cube reactor system , 2006 .

[43]  C. Bolm,et al.  Catalytic asymmetric approaches towards enantiomerically enriched diarylmethanols and diarylmethylamines. , 2006, Chemical Society reviews.

[44]  S. Morin,et al.  Catalysis in capillaries by Pd thin films using microwave-assisted continuous-flow organic synthesis (MACOS). , 2006, Angewandte Chemie.

[45]  Monica Brivio,et al.  Miniaturized continuous flow reaction vessels: influence on chemical reactions. , 2006, Lab on a chip.

[46]  A. Riisager,et al.  Supported Ionic Liquid Phase (SILP) Catalysis: An Innovative Concept for Homogeneous Catalysis in Continuous Fixed-Bed Reactors , 2006 .

[47]  S. Haswell,et al.  Asymmetric Catalysis in a Micro Reactor : Ce, Yb and Lu Catalysed Enantioselective Addition of Trimethylsilyl Cyanide to Benzaldehyde , 2004 .

[48]  Paul Watts,et al.  Benchmarking of Microreactor Applications , 2004 .

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

[50]  O. Reiser,et al.  Improved synthesis of aza-bis(oxazoline) ligands. , 2003, The Journal of organic chemistry.

[51]  Paul Watts,et al.  Continuous flow reactors for drug discovery. , 2003, Drug discovery today.

[52]  Paul Watts,et al.  Green chemistry: synthesis in micro reactors , 2003 .

[53]  M. Vicent,et al.  New supported beta-amino alcohols as efficient catalysts for the enantioselective addition of diethylzinc to benzaldehyde under flow conditions. , 2002, Organic letters.

[54]  Paul Watts,et al.  Micro reactors: principles and applications in organic synthesis , 2002 .

[55]  M. Lemaire,et al.  Aryl-aryl bond formation one century after the discovery of the Ullmann reaction. , 2002, Chemical reviews.

[56]  U. Hoffmann,et al.  PASSflow-Synthesen mit funktionalisierten monolithischen Polymer/Glas-Kompositen in Mikroreaktoren , 2001 .

[57]  Andreas Kirschning,et al.  PASSflow Syntheses Using Functionalized Monolithic Polymer/Glass Composites in Flow-Through Microreactors. , 2001, Angewandte Chemie.

[58]  Glos,et al.  Aza-bis(oxazolines): new chiral ligands for asymmetric catalysis , 2000, Organic letters.

[59]  Santiago V. Luis,et al.  Chemical reactions and processes under flow conditions , 2009 .

[60]  R. Mathies,et al.  Lawrence Berkeley National Laboratory Title : High-Temperature Microfluidic Synthesis of CdSe Nanocrystals in Nanoliter Droplets , 2009 .

[61]  Ferenc Darvas,et al.  Continuous-flow high pressure hydrogenation reactor for optimization and high-throughput synthesis. , 2006, Journal of combinatorial chemistry.

[62]  S. Buchwald,et al.  Industrial-Scale Palladium-Catalyzed Coupling of Aryl Halides and Amines –A Personal Account , 2006 .

[63]  Andreas Kirschning,et al.  Applications of immobilized catalysts in continuous flow processes. , 2004, Topics in current chemistry.

[64]  C. P. Mehnert.  Supported ionic liquid catalysis. , 2004, Chemistry.

[65]  Franck F. Lepifre,et al.  Combining the use of solid‐supported transition metal catalysis with microwave irradiation in solution‐phase parallel library synthesis , 2004, Molecular Diversity.

[66]  P. Hodge,et al.  Asymmetric synthesis of 1-phenylpropanol using polymer-supported chiral catalysts in simple bench-top flow systems† , 1999 .