Indium-Catalyzed Reductive Bromination of Carboxylic Acids Leading to Alkyl Bromides

Toshimitsu Moriya, Shinichiro Yoneda, Keita Kawana, Reiko Ikeda, Takeo Konakahara and Norio Sakai*

*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

T. Moriya, S. Yoneda, K. Kawana, R. Ikeda, T. Konakahara, N. Sakai, Org. Lett., 2012, 14, 4842-4845.

DOI: 10.1021/ol302168q

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Abstract

The combination of 1,1,3,3-tetramethyldisiloxane (TMDS) and trimethylbromosilane (Me₃SiBr) enabled a direct bromination of carboxylic acids in the presence of indium bromide (InBr₃) as catalyst. The reducing system was tolerant to several functional groups and produced the corresponding alkyl bromides in very good yields.

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Indium(III)-Catalyzed Reductive Bromination and Iodination of Carboxylic Acids to Alkyl Bromides and Iodides: Scope, Mechanism, and One-Pot Transformation to Alkyl Halides and Amine Derivatives

T. Moriya, S. Yoneda, K. Kawana, R. Ikeda, T. Konakahara, N. Sakai, J. Org. Chem., 2013, 78, 10642-10650.

Indium(III)-Catalyzed One-Pot Synthesis of Alkyl Cyanides from Carboxylic Acids

T. Moriya, K. Shoji, S. Yoneda, R. Ikeda, T. Konakahara, N. Sakai, Synthesis, 2013, 45, 3233-3238.

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Key Words

alkyl bromides, TMDS, Indium

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ID: J54-Y2012-3060