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

被引：561

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 46期

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

页码：18566 / 18569

页数：4

共 30 条

[1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
Alberico, Dino
Scott, Mark E.
Lautens, Mark
[J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
[2] Theoretical Investigation into the Mechanism of Reductive Elimination from Bimetallic Palladium Complexes
Ariafard, Alireza
Hyland, Christopher J. T.
Canty, Allan J.
Sharma, Manab
Yates, Brian F.
[J]. INORGANIC CHEMISTRY, 2011, 50 (14) : 6449 - 6457
[3] PHOTOCATALYSIS OF THE PSCHORR REACTION BY TRIS-(2,2'-BIPYRIDYL)RUTHENIUM(II) IN THE PHENANTHRENE SERIES
CANOYELO, H
DERONZIER, A
[J]. 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
CANOYELO, H
DERONZIER, A
[J]. 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
CANOYELO, H
DERONZIER, A
[J]. 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
CANOYELO, H
DERONZIER, A
[J]. 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
Chen, Xiao
Engle, Keary M.
Wang, Dong-Hui
Yu, Jin-Quan
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) : 5094 - 5115
[9] Catalytic C-C coupling through C-H arylation of arenes or heteroarenes
Chiusoli, Gian Paolo
Catellani, Marta
Costa, Mirco
Motti, Elena
Della Ca', Nicola
Maestri, Giovanni
[J]. 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
Daugulis, Olafs
[J]. C-H ACTIVATION, 2010, 292 : 57 - 84

← 1 2 3 →