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Synthesis of α-Heterosubstituted Ketones Through Sulfur Mediated Difunctionalization of Internal Alkynes

preprint
submitted on 24.01.2019 and posted on 25.01.2019 by Zhong Zhang, Hongguang Du, Jiaxi Xu, Pingfan Li
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 the triflic anhydride activated diphenyl sulfoxide to give a sulfonium vinyl triflate intermediate, hydrolysis to give the 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.

Funding

National Natural Science Foundation of China

Fundamental Research Funds for the Central Universities

History

Email Address of Submitting Author

lipf@mail.buct.edu.cn

Institution

Beijing University of Chemical Technology

Country

China

ORCID For Submitting Author

0000-0002-0056-9243

Declaration of Conflict of Interest

no conflict of interest

Exports