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 (free Supporting Information)
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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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T. Moriya, S. Yoneda, K. Kawana, R. Ikeda, T. Konakahara, N. Sakai, J. Org. Chem., 2013, 78, 10642-10650.
T. Moriya, K. Shoji, S. Yoneda, R. Ikeda, T. Konakahara, N. Sakai, Synthesis, 2013, 45, 3233-3238.