Selective arylation of 2-substituted indoles towards 1,2-and 2,3-functional indoles directed through the catalytic system

被引：24

作者：

Djakovitch, Laurent ^{[1
]}

Rouge, Pascal ^{[1
]}

Zaidi, Rabah ^{[1
]}

机构：

[1] Univ Lyon 1, IRCELYON, CNRS, UMR 5256, F-69626 Villeurbanne, France

来源：

CATALYSIS COMMUNICATIONS | 2007年 / 8卷 / 11期

关键词：

palladium; substituted indoles; N-arylation; C-arylation; O-ALKYNYLTRIFLUOROACETANILIDES; 2,3-DISUBSTITUTED INDOLES; ARYL BROMIDES; PALLADIUM; HETEROCYCLES; CYCLIZATION; ANNULATION; AMINATION;

D O I：

10.1016/j.catcom.2007.01.009

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A simple palladium catalysed procedure for the synthesis of 1,2- and 2,3-disubstituted indoles is reported. It was found that the selectivity of the reaction, i.e. the N1-versus the C3-arylation of 2-functional indoles was mainly directed by electronic factors. Fine tuning of the reaction conditions and the right choice of the substrates allowed a full selective N1-(ArI,[Pd(OAc)(2)], PPh3) or C3 (ArBr, [Pd(OAc)(2)], AgBF4) arylation. Using only 1 mol% Pd-catalyst gave up to 92% isolated yield of expected compound. (c) 2007 Elsevier B.V. All rights reserved.

引用

页码：1561 / 1566

页数：6

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