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.
HSiCl3-mediated Reduction of Nitro-derivatives to Amines : Is Tertiary amine-stabilized SiCl2 the Actual Reducing Species? / M. Orlandi, M. Benaglia, F. Tosi, R. Annunziata, F. Cozzi. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 81:7(2016), pp. 3037-3041.
HSiCl3-mediated Reduction of Nitro-derivatives to Amines : Is Tertiary amine-stabilized SiCl2 the Actual Reducing Species?
M. Orlandi;M. Benaglia;R. Annunziata;F. Cozzi
2016
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.
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