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Synthesis of α-heterosubstituted ketones through sulfur mediated difunctionalization of internal alkynes.

Research paper by Zhong Z Zhang, Yuzheng Y Luo, Hongguang H Du, Jiaxi J Xu, Pingfan P Li

Indexed on: 13 Jun '19Published on: 12 Jun '19Published in: Chemical Science



Abstract

Synthesis of α-heterosubstituted ketones was achieved through sulfur mediated difunctionalization of internal alkynes in one pot. The reaction design involves: phenyl substituted internal alkyne attacking triflic anhydride activated diphenyl sulfoxide to give a sulfonium vinyl triflate intermediate, hydrolysis to give an α-sulfonium ketone, and then substitution with various nucleophiles. This method provides a unified route to access α-amino ketones, α-acyloxy ketones, α-thio ketones, α-halo ketones, α-hydroxy ketones, and related heterocyclic structures, in a rapid fashion.