Room-Temperature C-H Arylation: Merger of Pd-Catalyzed C-H Functionalization and Visible-Light Photocatalysis

被引:575
作者
Kalyani, Dipannita [1 ]
McMurtrey, Kate B. [1 ]
Neufeldt, Sharon R. [1 ]
Sanford, Melanie S. [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
关键词
ARYL BOND FORMATION; COUPLING REACTIONS; PSCHORR REACTION; DIAZONIUM SALTS; PHOTO-OXIDATION; PALLADIUM; ACTIVATION; COMPLEXES; SYSTEM; SERIES;
D O I
10.1021/ja208068w
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This communication describes the development of a room-temperature ligand-directed C-H arylation reaction using aryldiazonium salts. This was achieved by the successful merger of palladium-catalyzed C-H functionalization and visible-light photoredox catalysis. The new method is general for a variety of directing groups and tolerates many common functional groups.
引用
收藏
页码:18566 / 18569
页数:4
相关论文
共 30 条
[1]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[2]   Theoretical Investigation into the Mechanism of Reductive Elimination from Bimetallic Palladium Complexes [J].
Ariafard, Alireza ;
Hyland, Christopher J. T. ;
Canty, Allan J. ;
Sharma, Manab ;
Yates, Brian F. .
INORGANIC CHEMISTRY, 2011, 50 (14) :6449-6457
[3]   PHOTOCATALYSIS OF THE PSCHORR REACTION BY TRIS-(2,2'-BIPYRIDYL)RUTHENIUM(II) IN THE PHENANTHRENE SERIES [J].
CANOYELO, H ;
DERONZIER, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (06) :1093-1098
[4]   PHOTO-OXIDATION OF SOME CARBINOLS BY THE RU(II) POLYPYRIDYL COMPLEX ARYL DIAZONIUM SALT SYSTEM [J].
CANOYELO, H ;
DERONZIER, A .
TETRAHEDRON LETTERS, 1984, 25 (48) :5517-5520
[5]   PHOTO-OXIDATION OF TRIS(2,2'-BIPYRIDINE)RUTHENIUM(II) BY PARA-SUBSTITUTED BENZENE DIAZONIUM SALTS IN ACETONITRILE 2-COMPARTMENT PHOTOELECTROCHEMICAL CELL APPLICATIONS [J].
CANOYELO, H ;
DERONZIER, A .
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS I, 1984, 80 :3011-3019
[6]   PHOTOCATALYSIS OF THE PSCHORR REACTION BY RU(BPY)32+ IN THE FLUORENONE, FLUORENE AND DIBENZOFURAN SERIES [J].
CANOYELO, H ;
DERONZIER, A .
JOURNAL OF PHOTOCHEMISTRY, 1987, 37 (02) :315-321
[7]  
CANOYELO H, 1987, NEW J CHEM, V11, P479
[8]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[9]   Catalytic C-C coupling through C-H arylation of arenes or heteroarenes [J].
Chiusoli, Gian Paolo ;
Catellani, Marta ;
Costa, Mirco ;
Motti, Elena ;
Della Ca', Nicola ;
Maestri, Giovanni .
COORDINATION CHEMISTRY REVIEWS, 2010, 254 (5-6) :456-469
[10]   Palladium and Copper Catalysis in Regioselective, Intermolecular Coupling of C-H and C-Hal Bonds [J].
Daugulis, Olafs .
C-H ACTIVATION, 2010, 292 :57-84