Copper-Catalyzed Synthesis of Benzo[b]thiophenes and Benzothiazoles Using Thiocarboxylic Acids as a Coupling Partner

Hui Yu*, Meishu Zhang and Yuzhe Li

*Department of Chemistry, Tongji University, 1239 Siping Road, Yangpu, Shanghai 200092, PR China, Email: yuhuitongji.edu.cn

H. Yu, M. Zhang, Y. Li, J. Org. Chem., 2013, 78, 8898-8899.

DOI: 10.1021/jo401353w

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Abstract

In the presence of CuI and 1,10-phen, and n-Pr₃N as the base, (2-iodobenzyl)triphenylphosphonium bromide and (2-iodophenylimino)triphenylphosphorane reacted efficiently with thiocarboxylic acids to give benzo[b]thiophenes and benzothiazoles in good yields via sequential Ullmann-type C-S bond coupling and subsequent Wittig reaction.

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Key Words

benzothiophenes, benzothiazoles, Ullmann coupling, Wittig reaction

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ID: J42-Y2013