Metal‐Free Deoxygenation of Amine N ‐Oxides: Synthetic and Mechanistic Studies

William Lecroq (1) , Jules Schleinitz (2) , Mallaury Billoue (1) , Anna Perfetto (3) , Annie-Claude Gaumont (1) , Jacques Lalevée (4) , Ilaria Ciofini (3) , Laurence Grimaud (2, 5) , Sami Lakhdar (6)

1 ENSICAEN - École Nationale Supérieure d'Ingénieurs de Caen
2 ENS-PSL - École normale supérieure - Paris
3 ENSCP - Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL
4 Université de Haute-Alsace (UHA) - Université de Haute-Alsace (UHA) Mulhouse - Colmar
5 LBM UMR 7203 - Laboratoire des biomolécules
6 UT3 - Université Toulouse III - Paul Sabatier

We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal–free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides. Supporting information for this article is given via a link at the end of the document.

Domaines: Catalyse

William Lecroq, Jules Schleinitz, Mallaury Billoue, Anna Perfetto, Annie-Claude Gaumont, et al.. Metal‐Free Deoxygenation of Amine N ‐Oxides: Synthetic and Mechanistic Studies. ChemPhysChem, 2021, 22 (12), pp.1237-1242. ⟨10.1002/cphc.202100108⟩. ⟨hal-03306177⟩