Issue 19, 2019

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.

Graphical abstract: Synthesis of α-heterosubstituted ketones through sulfur mediated difunctionalization of internal alkynes

Supplementary files

Article information

Article type
Edge Article
Submitted
31 1 2019
Accepted
15 4 2019
First published
16 4 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 5156-5161

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

Z. Zhang, Y. Luo, H. Du, J. Xu and P. Li, Chem. Sci., 2019, 10, 5156 DOI: 10.1039/C9SC00568D

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