Literature DB >> 26937628

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

Manuel Orlandi1, Maurizio Benaglia1, Filippo Tosi1, Rita Annunziata1, Franco Cozzi1.   

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.

Entities:  

Year:  2016        PMID： 26937628     DOI： 10.1021/acs.joc.6b00191

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  3 in total

1.  Continuous-flow synthesis of primary amines: Metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane.

Authors:  Riccardo Porta; Alessandra Puglisi; Giacomo Colombo; Sergio Rossi; Maurizio Benaglia
Journal:  Beilstein J Org Chem       Date:  2016-12-05       Impact factor: 2.883

2.  A one pot protocol to convert nitro-arenes into N-aryl amides.

Authors:  Elisabetta Massolo; Margherita Pirola; Alessandra Puglisi; Sergio Rossi; Maurizio Benaglia
Journal:  RSC Adv       Date:  2020-01-23       Impact factor: 4.036

3.  Enantioselective Flow Synthesis of Rolipram Enabled by a Telescoped Asymmetric Conjugate Addition-Oxidative Aldehyde Esterification Sequence Using in Situ-Generated Persulfuric Acid as Oxidant.

Authors:  Bence S Nagy; Patricia Llanes; Miquel A Pericas; C Oliver Kappe; Sándor B Ötvös
Journal:  Org Lett       Date:  2022-01-20       Impact factor: 6.005
  3 in total

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