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 jan 2019
Accepted
15 apr 2019
First published
16 apr 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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