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

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.

SUBMITTER: Zhang Z 

PROVIDER: S-EPMC6524669 | biostudies-other | 2019 May

REPOSITORIES: biostudies-other