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Highly Regio‐ and Stereoselective Intermolecular Seleno‐ and Thioamination of Alkynes
Author(s) -
Zheng Guangfan,
Zhao Jinbo,
Li Zhanyu,
Zhang Qiao,
Sun Jiaqiong,
Sun Haizhu,
Zhang Qian
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504534
Subject(s) - stereoselectivity , amination , chemistry , reagent , chalcogen , intermolecular force , combinatorial chemistry , substrate (aquarium) , functional group , stereochemistry , organic chemistry , catalysis , molecule , polymer , oceanography , geology
By using N ‐fluorobenzenesulfonimide as both the oxidant and the amination reagent, we have realized the first example of the intermolecular chalcogenative amination of alkynes, which grants facile, highly regio‐ and stereoselective access to chalcogenated enamides. The reaction features mild conditions, high yields and selectivities, remarkably broad substrate scope, and excellent functional group tolerance. Mechanistic studies indicate the in situ generated chalcogen imidates to be the actual reactive species, which in turn, has clarified the mechanism of related transformations. These reactions represent significant additions to the development of the highly selective amino bisfunctionalization of alkynes.