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 Nah 2023
Accepted
10 Agd 2023
First published
12 Agd 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements