Organic letters

Controlled Synthesis of 2-and 3-Substituted Benzo [b] furans

T Pei, C Chen, L DiMichele, IW Davies

Index: Pei, Tao; Chen, Cheng-Yi; Dimichele, Lisa; Davies, Ian W. Organic Letters, 2010 , vol. 12, # 21 p. 4972 - 4975

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Citation Number: 21

Abstract

A controlled regioselective synthesis of either C-2 or C-3 substituted benzo [b] furans from readily accessible 1-(2-hydroxyphenyl)-2-chloroethanones is described. Addition of a range of Grignard reagents to the α-chloro ketones generates alkoxide intermediates, which can form either 2-substituted benzo [b] furans via a [1, 2]-aryl migration or 3-substituted benzo [b] furans via a direct cyclization and dehydration sequence. A temperature-dependent [1, 2]- ...