Metal-Free, Visible-Light-Mediated Direct C-H Arylation of Heteroarenes with Aryl Diazonium Salts

被引：680

作者：

Hari, Durga Prasad ^{[1
]}

Schroll, Peter ^{[1
]}

Koenig, Burkhard ^{[1
]}

机构：

[1] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 06期

关键词：

PHOTOREDOX CATALYSIS; EOSIN-Y; ARENEDIAZONIUM SALTS; FURAN-DERIVATIVES; ORGANIC-SYNTHESIS; PSCHORR REACTION; BOND ARYLATION; PHOTOCATALYSIS; ORGANOCATALYSIS; CYCLOADDITIONS;

D O I：

10.1021/ja212099r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Visible light along with 1 mol % eosin Y catalyzes the direct C-H bond arylation of heteroarenes with aryl diazonium salts by a photoredox process. We have investigated the scope of the reaction for several aryl diazonium salts and heteroarenes. The general and easy procedure provides a transition-metal-free alternative for the formation of aryl-heteroaryl bonds.

引用

页码：2958 / 2961

页数：4

共 67 条

[41] Intermolecular Atom Transfer Radical Addition to Olefins Mediated by Oxidative Quenching of Photoredox Catalysts
Nguyen, John D.
Tucker, Joseph W.
Konieczynska, Marlena D.
Stephenson, Corey R. J.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) : 4160 - 4163
[42] Merging photoredox catalysis with organocatalysis: The direct asymmetric alkylation of aldehydes
Nicewicz, David A.
MacMillan, David W. C.
[J]. SCIENCE, 2008, 322 (5898) : 77 - 80
[43] Mechanism of Meerwein Arylation of Furan Derivatives
Obushak, N. D.
Lesyuk, A. I.
Gorak, Yu. I.
Matiichuk, V. S.
[J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (09) : 1375 - 1381
[44] Padon KS, 2001, J POLYM SCI POL CHEM, V39, P715, DOI 10.1002/1099-0518(20010301)39:5<715::AID-POLA1043>3.0.CO
[45] 2-O
[46] Photoredox Catalysis: A Mild, Operationally Simple Approach to the Synthesis of α-Trifluoromethyl Carbonyl Compounds
Pham, Phong V.
Nagib, David A.
MacMillan, David W. C.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (27) : 6119 - 6122
[47] Hydroxy- and Aminophenyl Radicals from Arenediazonium Salts
Pratsch, Gerald
Anger, Christian A.
Ritter, Katharina
Heinrich, Markus R.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) : 4104 - 4108
[48] Functionalization of the 3-Position of Thiophene and Benzo[b]thiophene Moieties by Palladium-Catalyzed C-C Bond Forming Reactions using Diazonium Salts
Raduan, Monica
Padrosa, Joaquim
Pla-Quintana, Anna
Parella, Teodor
Roglans, Anna
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (11-12) : 2003 - 2012
[49] Rondestvedt C.S., 1976, ORG REACT N Y, V24, P225, DOI DOI 10.1002/0471264180.0R024.03
[50] Visible light mediated azomethine ylide formation-photoredox catalyzed [3+2] cycloadditions
Rueping, Magnus
Leonori, Daniele
Poisson, Thomas
[J]. CHEMICAL COMMUNICATIONS, 2011, 47 (34) : 9615 - 9617

← 1 2 3 4 5 6 7 →