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HSiCl3-Mediated Reduction of Nitro-Derivatives to Amines: Is Tertiary Amine-Stabilized SiCl2 the Actual Reducing Species?

作者信息

Orlandi Manuel, Benaglia Maurizio, Tosi Filippo, Annunziata Rita, Cozzi Franco

机构信息

Dipartimento di Chimica, Università degli Studi di Milano , Via Golgi 19, 20133 Milano, Italy.

出版信息

J Org Chem. 2016 Apr 1;81(7):3037-41. doi: 10.1021/acs.joc.6b00191. Epub 2016 Mar 10.

DOI:10.1021/acs.joc.6b00191
PMID:26937628
Abstract

The mechanism of a recently reported, highly chemoselective metal-free protocol of wide general applicability for the reduction of aromatic and aliphatic nitro-derivatives to amines has been investigated. The reaction is supposed to occur through the generation of a Si(II) reducing species; quantum mechanical calculations, and spectroscopic and experimental data strongly suggest the tertiary amine-stabilized dichlorosilylene to be the most probable reducing agent.

摘要

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