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

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• 作者：Tao Pei ; Cheng-yi Chen ; Lisa DiMichele ; Ian W. Davies
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：November 5, 2010
• 年：2010
• 卷：12
• 期：21
• 页码：4972-4975
• 全文大小：196K
• 年卷期：v.12,no.21(November 5, 2010)
• ISSN：1523-7052

文摘

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]-aryl migration mechanism for the formation of 2-substituted benzo[b]furan is proposed.