Synthesis 2015; 47(20): 3179-3185
DOI: 10.1055/s-0034-1378850
paper
© Georg Thieme Verlag Stuttgart · New York

Indium(III)-Catalyzed Reduction of Nitrobenzenes to Anilines: Scope and Limitations

Norio Sakai*
Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda, Chiba 278-8510, Japan   Email: sakachem@rs.noda.tus.ac.jp
,
Shun Asama
Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda, Chiba 278-8510, Japan   Email: sakachem@rs.noda.tus.ac.jp
,
Takeo Konakahara
Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda, Chiba 278-8510, Japan   Email: sakachem@rs.noda.tus.ac.jp
,
Yohei Ogiwara
Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda, Chiba 278-8510, Japan   Email: sakachem@rs.noda.tus.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 30 April 2015

Accepted after revision: 18 May 2015

Publication Date:
15 July 2015 (online)


Abstract

We have demonstrated that a combination of indium(III) iodide and 1,1,3,3-tetramethyldisiloxane (TMDS) effectively catalyzes the chemoselective reduction of nitrobenzenes with a variety of functional groups (halogens, alkyl, alkoxy, hydroxy, ester, amino, amide, cyanide, thiol, and an alkene moiety), producing the corresponding aniline derivatives.

Supporting Information

 
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