Generation of Iminyl Copper Species from α-Azido Carbonyl Compounds and Their Catalytic C-C Bond Cleavage under an Oxygen Atmosphere

被引：103

作者：

Chiba, Shunsuke ^{[1
]}

Zhang, Line ^{[1
]}

Ang, Gim Yean ^{[1
]}

Hui, Benjamin Wei-Qiang ^{[1
]}

机构：

[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 09期

关键词：

PRIMARY AMIDES; VINYL AZIDES; NITRILES; ACIDS; TRANSFORMATION; DEHYDRATION; DERIVATIVES; CONVERSION; ALDOXIMES; CYANATION;

D O I：

10.1021/ol100522z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed reaction of a-azidocarbonyl compounds under an oxygen atmosphere is reported where nitriles are formed via C C bond cleavage of a transient Iminyl copper intermediate. The transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from alpha-azidocarbonyl compounds and their C C bond cleavage, where molecular oxygen (1 atm) is a prerequisite to achieve the catalytic process and one of the oxygen atoms of O-2 was found to be incorporated Into the beta-carbon fragment as a carboxylic acid.

引用

页码：2052 / 2055

页数：4

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