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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

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

Zhang Zhong Z Luo Yuzheng Y Du Hongguang H Xu Jiaxi J Li Pingfan P

Chemical science 20190416 19

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 ke ...[more]

PMID: 31183068

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