Copper-Catalyzed Aerobic Oxidative Cross-Dehydrogenative Coupling of Amine and α-Carbonyl Aldehyde: A Practical and Efficient Approach to α-Ketoamides with Wide Substrate Scope

被引：170
|
作者：
Zhang, Chun [2 ]
Zong, Xiaolin [2 ]
Zhang, Liangren [2 ]
Jiao, Ning [1 ]
机构：
[1] Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
[2] Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 13期
基金：
美国国家科学基金会;
关键词：
O-O BOND; MOLECULAR-OXYGEN; DIRECT ACCESS; PALLADIUM; AMIDATION; DIOXYGEN; REACTIVITY; COMPLEXES; ESTERIFICATION; ACYLATION;
D O I：
10.1021/ol301130u
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper-catalyzed aerobic oxidative cross-dehydrogenative coupling (CDC) of amine with alpha-carbonyl aldehyde has been developed. Many types of amines are tolerant in this transformation leading to various alpha-ketoamides compounds. Wide substrate scope, CDC strategy and using air as oxidant make this transformation highly efficient and practical. Molecular oxygen acts not only as the oxidant, but also as an initiator to trigger this catalytic process. Furthermore, mechanism studies show that carbonyl group of a-carbonyl aldehyde plays a role as the directing group to facilitate this chemical process.
引用
收藏
页码：3280 / 3283
页数：4
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