Highly Regio- and Stereoselective Intermolecular Seleno- and Thioamination of Alkynes
Highly Regio- and Stereoselective Intermolecular Seleno- and Thioamination of Alkynes
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炔烃的高度区域和立体选择性分子间硒和硫胺化
DOI：
10.1002/chem.201504534
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发表时间：
2016
影响因子：
4.3
通讯作者：
Zhang Qian
中科院分区：
文献类型：
--
作者：
Zheng Guangfan;Zhao Jinbo;Li Zhanyu;Zhang Qiao;Sun Jiaqiong;Sun Haizhu;Zhang Qian
通过使用N-氟苯磺酰亚胺作为氧化剂和胺化试剂，我们实现了炔烃分子间硫属胺化的第一个例子，它可以轻松、高度区域和立体选择性地获得硫属烯酰胺。该反应具有条件温和、产率和选择性高、底物范围极广、官能团耐受性优异等特点。机理研究表明，原位生成的硫属亚胺酸盐是实际的活性物质，这反过来又阐明了相关转化的机制。这些反应代表了对炔烃的高选择性氨基双官能化的发展的显着补充。
By usingN‐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.