Tetrahedron

[1, 2]-Aryl migration in the synthesis of substituted indoles: scope, mechanism, and high throughput experimentation

T Pei, DM Tellers, EC Streckfuss, C Chen, IW Davies

Index: Pei, Tao; Tellers, David M.; Streckfuss, Eric C.; Chen, Cheng-yi; Davies, Ian W. Tetrahedron, 2009 , vol. 65, # 16 p. 3285 - 3291

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Citation Number: 20

Abstract

A mild regioselective synthesis of substituted indoles from readily accessible 1-(2- aminophenyl)-2-chloroethanones is described. Addition of a range of carbon nucleophiles to α-chloro acetophenones 1 generates 2-substituted indoles 2 in moderate to excellent yields. A reaction mechanism involving a [1, 2]-aryl migration is proposed. This useful transformation is further examined using high throughput experimentation.