Copper(II)-Catalyzed Room Temperature Aerobic Oxidation of Hydroxamic Acids and Hydrazides to Acyl-Nitroso and Azo Intermediates, and Their Diels-Alder Trapping

被引：66

作者：

Chaiyaveij, Duangduan

Cleary, Leah

Batsanov, Andrei S.

Marder, Todd B. ^{[1
]}

Shea, Kenneth J.

Whiting, Andrew

机构：

[1] Univ Durham, Dept Chem, Ctr Sustainable Chem Proc, Sci Labs, Durham DH1 3LE, England

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 13期

基金：

英国工程与自然科学研究理事会;

关键词：

NITROSOCARBONYL COMPOUNDS; EFFICIENT; COMPLEX; BIS(METHOXYCARBONYLATION); FUNCTIONALIZATION; ACYLNITROSO; GENERATION; CHEMISTRY; ANALOGS;

D O I：

10.1021/ol201188d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

CuCl2, in the presence of a 2-ethyl-2-oxazoline ligand, is an effective catalyst for the room temperature, aerobic oxidation of hydroxamic acids and hydrazides, to acyl-nitroso and azo dienophiles respectively, which are efficiently trapped in situ via both inter- and intramolecular hetero-Diels-Alder reactions with dimes. Both inter- and intramolecular variants of the Diels-Alder reaction are suitable under the reaction conditions using a variety of solvents. Under the same conditions, an acyl hydrazide Was also oxidized to give an acyl-azo dienophile which was trapped intramolecularly by a diene.

引用

页码：3442 / 3445

页数：4

共 41 条

[1] The nitroso ene reaction: A regioselective and stereoselective allylic nitrogen functionalization of mechanistic delight and synthetic potential [J].