Issue 10, 2023

Regio- and stereoselective oxidative conversion of alkynes to sulfenylated α,β-unsaturated carbonyls

Abstract

The synthesis of enone moieties via the oxidation of internal alkynes under varied conditions is known. The use of propargyl units as the precursors of α,β-unsaturated aldehydes is rare. Herein, we present the synthesis of α-sulfenylated α,β-unsaturated aldehydes from terminal alkynes through the selective addition of a suitable oxidant to the key thiirenium ion intermediates. The mild conditions of this protocol enable the conversion of a vast range of terminal alkynes, bearing various functionalities or derived from drug and bioactive molecules, to their α,β-unsaturated aldehyde analogues with excellent chemo-, regio- and stereoselectivities.

Graphical abstract: Regio- and stereoselective oxidative conversion of alkynes to sulfenylated α,β-unsaturated carbonyls

Supplementary files

Article information

Article type
Research Article
Submitted
16 feb 2023
Accepted
10 apr 2023
First published
12 apr 2023

Org. Chem. Front., 2023,10, 2416-2421

Regio- and stereoselective oxidative conversion of alkynes to sulfenylated α,β-unsaturated carbonyls

M. Tang, Y. Wang, S. Huang and L. Xie, Org. Chem. Front., 2023, 10, 2416 DOI: 10.1039/D3QO00236E

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