Zheng Guangfan, Zhao Jinbo, Li Zhanyu, Zhang Qiao, Sun Jiaqiong, Sun Haizhu, Zhang Qian
Department of Chemistry, Northeast Normal University, 5268 Renmin Rd, Changchun, Jilin, 130024, China.
Chemistry. 2016 Mar 1;22(10):3513-3518. doi: 10.1002/chem.201504534. Epub 2016 Feb 2.
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.
