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

被引：3

作者：

Lecroq, William ^{[1
]}

Schleinitz, Jules ^{[2
]}

Billoue, Mallaury ^{[1
]}

Perfetto, Anna ^{[3
]}

Gaumont, Annie-Claude ^{[1
]}

Lalevee, Jacques ^{[4
]}

Ciofini, Ilaria ^{[3
]}

Grimaud, Laurence ^{[2
]}

Lakhdar, Sami ^{[5
]}

机构：

[1] Normandie Univ, LCMT, ENSICAEN, UNICAEN,CNRS, 6 Blvd Marechal Juin, F-14000 Caen, France

[2] PSL Univ, Sorbonne Univ, Lab Biomol, LBM,Dept Chim,Ecole Normale Super,CNRS, F-75005 Paris, France

[3] PSL Univ, Inst Chem Life & Hlth Sci I CLeHS, Chim ParisTech, CNRS, 11 Rue P&M Curie, F-75005 Paris, France

[4] Univ Haute Alsace, CNRS, UMR 7361, IS2 M, F-68100 Mulhouse, France

[5] Univ Paul Sabatier, Lab Heterochim Fondamentale & Appl LHFA, UMR 5069, 118 Route Narbonne, F-31062 Toulouse 09, France

来源：

CHEMPHYSCHEM | 2021年 / 22卷 / 12期

基金：

欧洲研究理事会;

关键词：

deoxygenation; mechanisms; photochemistry; organocatalysis; selectivity; DENSITY-FUNCTIONAL METHODS; ALKYLATION; SULFOXIDES; REDUCTION; ENERGIES; ESTERS;

D O I：

10.1002/cphc.202100108

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

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.

引用

页码：1237 / 1242

页数：6

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