Single-Step Thioetherification by Indium-Catalyzed Reductive Coupling of Carboxylic Acids with Thiols

Norio Sakai*, Takahiro Miyazaki, Tomohiro Sakamoto, Takuma Yatsuda, Toshimitsu Moriya, Reiko Ikeda and Takeo Konakahara

*Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda, Chiba 278-8510, Japan, Email: sakachemrs.noda.tus.ac.jp

N. Sakai, T. Miyazaki, T. Sakamoto, T. Yatsuda, T. Moriya, R. Ikeda, T. Konakahara, Org. Lett., 2012, 14, 4366-4369.

DOI: 10.1021/ol302109v

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Abstract

A reducing system combined with InBr₃ and 1,1,3,3-tetramethyldisiloxane (TMDS) enables a direct thioetherification of various aromatic carboxylic acids and thiols in a one-pot procedure, whereas a system combined with InI₃ and TMDS underwent thioetherification of aliphatic carboxylic acids with thiols.

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Key Words

benzylation, alkylation, 1,1,3,3-tetramethyldisiloxane

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ID: J54-Y2012-2800