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Metal‐Free Deoxygenation of Amine N ‐Oxides: Synthetic and Mechanistic Studies
Author(s) -
Lecroq William,
Schleinitz Jules,
Billoue Mallaury,
Perfetto Anna,
Gaumont AnnieClaude,
Lalevée Jacques,
Ciofini Ilaria,
Grimaud Laurence,
Lakhdar Sami
Publication year - 2021
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.202100108
Subject(s) - deoxygenation , amine gas treating , phenylsilane , chemistry , reactivity (psychology) , metal , redox , combinatorial chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Abstract 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.