Radical Carbon-Carbon Bond Formations Enabled by Visible Light Active Photocatalysts

被引:29
作者
Wallentin, Carl-Johan [1 ]
Nguyen, John D. [1 ]
Stephenson, Corey R. J. [1 ]
机构
[1] Boston Univ, Dept Chem, Boston, MA 02215 USA
关键词
Carbon-carbon bond; Flow reactor; Photocatalysis; Radical; Visible light; C-H FUNCTIONALIZATION; PHOTOREDOX CATALYSIS; ELECTRON-TRANSFER; ELECTROCHEMISTRY; PHOTOCHEMISTRY; PHOTOPHYSICS; CYCLIZATION; HALIDES;
D O I
10.2533/chimia.2012.394
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This mini-review highlights the Stephenson group's contribution to the field of photoredox catalysis with emphasis on carbon-carbon bond formation. The realization of photoredox mediated reductive dehalogenation initiated investigations toward both intra- and intermolecular coupling reactions. These reactions commenced via visible light-mediated reduction of activated halogens to give carbon-centered radicals that were subsequently involved in carbon-carbon bond forming transformations. The developed protocols using Ru and Ir based polypyridyl complexes as photoredox catalysts were further tuned to efficiently catalyze overall redox neutral atom transfer radical addition reactions. Most recently, a simplistic flow reactor technique has been utilized to affect a broad scope of photocatalytic transformations with significant enhancement in reaction efficiency.
引用
收藏
页码:394 / 398
页数:5
相关论文
共 31 条
[1]  
Albini A., 2010, Handbook of synthetic photochemistry
[2]   OUTER-SPHERE DISSOCIATIVE ELECTRON-TRANSFER TO ORGANIC-MOLECULES - A SOURCE OF RADICALS OR CARBANIONS - DIRECT AND INDIRECT ELECTROCHEMISTRY OF PERFLUOROALKYL BROMIDES AND IODIDES [J].
ANDRIEUX, CP ;
GELIS, L ;
MEDEBIELLE, M ;
PINSON, J ;
SAVEANT, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3509-3520
[3]   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-+
[4]   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
[5]   Photocatalytic reductive cyclizations of enones: Divergent reactivity of photogenerated radical and radical anion intermediates [J].
Du, Juana ;
Espelt, Laura Ruiz ;
Guzei, Ilia A. ;
Yoon, Tehshik P. .
CHEMICAL SCIENCE, 2011, 2 (11) :2115-2119
[6]   Photochemistry and photophysics of coordination compounds: Iridium [J].
Flamigni, Lucia ;
Barbieri, Andrea ;
Sabatini, Cristiana ;
Ventura, Barbara ;
Barigelletti, Francesco .
PHOTOCHEMISTRY AND PHOTOPHYSICS OF COORDINATION COMPOUNDS II, 2007, 281 :143-203
[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]   Total Synthesis of (+)-Gliocladin C Enabled by Visible-Light Photoredox Catalysis [J].
Furst, Laura ;
Narayanam, Jagan M. R. ;
Stephenson, Corey R. J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (41) :9655-9659
[9]   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
[10]  
HEDSTRAND DM, 1978, TETRAHEDRON LETT, P1255