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An Unexpected Potassium Iodide‐Promoted Nucleophilic Substitution Reaction between 2‐Acyloxy‐2 H ‐azirines and Carboxylic Acids
Author(s) -
Duan Xiyan,
Yang Kun,
Liu Jianwei,
Kong Xianglei,
Liang Ju,
Zhou Dongju,
Zhou Huiyun,
Zhang Yanping,
Liu Ning,
Feng Shuxiao,
Gu Guangna,
Lu Jun,
Song Nazi,
Zhang Dongliang,
Ma Junying
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600435
Subject(s) - chemistry , nucleophilic substitution , nucleophile , iodide , potassium , iodine , medicinal chemistry , carboxylic acid , substitution reaction , organic chemistry , catalysis
The acyloxy group of 2‐acyloxy‐2 H ‐azirines has been displaced by carboxylic acids to generate the corresponding 2‐acyloxy‐2 H ‐azirines by using potassium iodide as a promotor. This metal‐free method can be performed with a wide scope of substrates readily generating products in moderate to high yields. It also represents an example of nucleophilic substitution between esters and carboxylic acids under metal‐free reaction conditions for the first time.