Amide Synthesis by Nucleophilic Attack of Vinyl Azides**

被引：93

作者：

Zhang, Feng-Lian ^{[1
]}

Wang, Yi-Feng ^{[1
]}

Lonca, Geoffroy Herve ^{[1
]}

Zhu, Xu ^{[1
]}

Chiba, Shunsuke ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 17期

关键词：

amides; nitrilium ions; nucleophilic attack; rearrangement; vinyl azides; TRACELESS STAUDINGER LIGATION; ASYMMETRIC SCHMIDT REACTION; RING-EXPANSION; BOND FORMATION; 1,3-DICARBONYL COMPOUNDS; HYDROXYALKYL AZIDES; DIVERGENT SYNTHESIS; COUPLING REAGENTS; ENOLATE ADDITIONS; MANNICH REACTIONS;

D O I：

10.1002/anie.201400938

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A method for the synthesis of amide-containing molecules was developed using vinyl azides as an enamine-type nucleophile towards carbon electrophiles, such as imines, aldehydes, and carbocations that were generated from alcohols in the presence of BF3OEt2. After nucleophilic attack of the vinyl azide, a substituent of the resulting iminodiazonium ion intermediate migrates to form a nitrilium ion, which is hydrolyzed to afford the corresponding amide.

引用

页码：4390 / 4394

页数：5

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