The Development of Visible-Light Photoredox Catalysis in Flow

被引:134
作者
Garlets, Zachary J. [1 ]
Nguyen, John D. [1 ]
Stephenson, Corey R. J. [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
关键词
Photochemistry; Radicals; Radical reactions; Redox chemistry; C-H FUNCTIONALIZATION; ORGANIC-SYNTHESIS; PHOTOCHEMISTRY; REAGENT; REACTOR; SYSTEM; BATCH;
D O I
10.1002/ijch.201300136
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Visible-light photoredox catalysis has recently emerged as a viable alternative for radical reactions otherwise carried out with tin and boron reagents. It has been recognized that by merging photoredox catalysis with flow chemistry, slow reaction times, lower yields, and safety concerns may be obviated. While flow reactors have been successfully applied to reactions carried out with UV light, only recent developments have demonstrated the same potential of flow reactors for the improvement of visible-light-mediated reactions. This review examines the initial and continuing development of visible-light-mediated photoredox flow chemistry by exemplifying the benefits of flow chemistry compared with conventional batch techniques.
引用
收藏
页码:351 / 360
页数:10
相关论文
共 36 条
[1]   A Photoflow Reactor for the Continuous Photoredox-Mediated Synthesis of C-Glycoamino Acids and C-Glycolipids [J].
Andrews, R. Stephen ;
Becker, Jennifer J. ;
Gagne, Michel R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (17) :4140-4143
[2]   Visible-light-mediated photochemistry: accelerating Ru(bpy)32+-catalyzed reactions in continuous flow [J].
Bou-Hamdan, Farhan R. ;
Seeberger, Peter H. .
CHEMICAL SCIENCE, 2012, 3 (05) :1612-1616
[3]   Continuous flow photolysis of aryl azides: Preparation of 3H-azepinones [J].
Bou-Hamdan, Farhan R. ;
Levesque, Francois ;
O'Brien, Alexander G. ;
Seeberger, Peter H. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :1124-1129
[4]   A biomolecule-compatible visible-light-induced azide reduction from a DNA-encoded reaction-discovery system [J].
Chen, Yiyun ;
Kamlet, Adam S. ;
Steinman, Jonathan B. ;
Liu, David R. .
NATURE CHEMISTRY, 2011, 3 (02) :146-153
[5]   Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization [J].
Condie, Allison G. ;
Gonzalez-Gomez, Jose C. ;
Stephenson, Corey R. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) :1464-+
[6]   Visible-light-mediated conversion of alcohols to halides [J].
Dai, Chunhui ;
Narayanam, Jagan M. R. ;
Stephenson, Corey R. J. .
NATURE CHEMISTRY, 2011, 3 (02) :140-145
[7]   Functionally Diverse Nucleophilic Trapping of Iminium Intermediates Generated Utilizing Visible Light [J].
Freeman, David B. ;
Furst, Laura ;
Condie, Allison G. ;
Stephenson, Corey R. J. .
ORGANIC LETTERS, 2012, 14 (01) :94-97
[8]   Visible Light-Mediated Intermolecular C-H Functionalization of Electron-Rich Heterocycles with Malonates [J].
Furst, Laura ;
Matsuura, Bryan S. ;
Narayanam, Jagan M. R. ;
Tucker, Joseph W. ;
Stephenson, Corey R. J. .
ORGANIC LETTERS, 2010, 12 (13) :3104-3107
[9]   NOVEL REAGENT SYSTEM FOR CONVERTING A HYDROXY-GROUP INTO AN IODO-GROUP IN CARBOHYDRATES WITH INVERSION OF CONFIGURATION [J].
GAREGG, PJ ;
SAMUELSSON, B .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (22) :978-980
[10]   Development of an Automated Microfluidic Reaction Platform for Multidimensional Screening: Reaction Discovery Employing Bicyclo[3.2.1]octanoid Scaffolds [J].
Goodell, John R. ;
McMullen, Jonathan P. ;
Zaborenko, Nikolay ;
Maloney, Jason R. ;
Ho, Chuan-Xing ;
Jensen, Klavs F. ;
Porco, John A., Jr. ;
Beeler, Aaron B. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) :6169-6180