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
收藏
页码：2052 / 2055
页数：4
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