Iron-catalyzed oxidative homo-coupling of indoles via C-H cleavage

被引：44
作者：
Niu, Tianmin [1 ]
Zhang, Yuhong [1 ]
机构：
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 52期
关键词：
3,3 '-Biindolyl; Iron catalyst; C-H activation; Homo-coupling; ARYL HALIDES; DIRECT FUNCTIONALIZATION; DIRECT ARYLATION; BOND FORMATION; N-ARYLATION; DERIVATIVES; ACTIVATION; BROMIDES; ALKYLATION; ALDEHYDES;
D O I：
10.1016/j.tetlet.2010.10.088
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new method for the homo-coupling of indoles has been developed by the use of FeCl3 as catalyst and molecular oxygen as the only oxidant. The protocol provides a practical and straightforward approach toward 3,3'-biindolyls. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6847 / 6851
页数：5
相关论文
共 78 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]   Palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes.: An approach to 2-substituted 3-alkynylindoles and 2-substituted 3-acylindoles [J].
Arcadi, A ;
Cacchi, S ;
Fabrizi, G ;
Marinelli, F ;
Parisi, LM .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6213-6217
[3]   THE CHLORINATION OF INDOLES BY COPPER(II) CHLORIDE [J].
BALOGHHERGOVICH, E ;
SPEIER, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (12) :2305-2308
[4]   Synthesis and resolution of 2,2'-bis-diphenylphosphino[3,3']biindolyl; A new atropisomeric ligand for transition metal catalysis [J].
Berens, U ;
Brown, JM ;
Long, J ;
Selke, R .
TETRAHEDRON-ASYMMETRY, 1996, 7 (01) :285-292
[5]   Iron-catalyzed reactions in organic synthesis [J].
Bolm, C ;
Legros, J ;
Le Paih, J ;
Zani, L .
CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254
[6]   Iron-catalyzed intramolecular O-arylation:: Synthesis of 2-aryl benzoxazoles [J].
Bonnamour, Julien ;
Bolm, Carsten .
ORGANIC LETTERS, 2008, 10 (13) :2665-2667
[7]   Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides [J].
Brasche, Gordon ;
Garcia-Fortanet, Jorge ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2008, 10 (11) :2207-2210
[8]   2,2'-DIPHENYL-DELTA-3,3'-BI-3H-INDOLE-1,1'-DIOXIDE - COMPETITIVE DEMETHYLATION AND REDOX REACTIONS [J].
BRUNI, P ;
CONTI, C ;
TOSI, G .
MONATSHEFTE FUR CHEMIE, 1988, 119 (11) :1311-1316
[9]   2-substituted 3-aryl- and 3-heteroarylindoles by the palladium-catalyzed reaction of o-trifluoroacetanilides with aryl bromides and triflates [J].
Cacchi, S ;
Fabrizi, G ;
Lamba, D ;
Marinelli, F ;
Parisi, LM .
SYNTHESIS-STUTTGART, 2003, (05) :728-734
[10]   Biaryl synthesis via direct arylation: Establishment of an efficient catalyst for intramolecular processes [J].
Campeau, LC ;
Parisien, M ;
Leblanc, M ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9186-9187
12345678