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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

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, J. Org. Chem., 2013, 78, 10642-10650.

DOI: 10.1021/jo401529j (free Supporting Information)


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Abstract

A highly effective indium(III)-catalyzed reductive bromination or iodination of various carboxylic acids with 1,1,3,3-tetramethyldisiloxane (TMDS) and a halogen source tolerates many functional groups. This indium catalytic system is also applicable to the reductive iodination of aldehyded, acyl chlorides, and esters. Furthermore, this reducing system can be applied to the one-pot synthesis of alkyl halides and amine derivatives.

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

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


Key Words

alkyl iodides, TMDS, indium, iodine


ID: J42-Y2013