Issue 19, 2019

A rhodium-catalysed Sonogashira-type coupling exploiting C–S functionalisation: orthogonality with palladium-catalysed variants

Abstract

This report concerns the development of an efficient Sonogashira-type coupling of arylmethylsulfides and terminal alkynes to generate aryl alkyne motifs. Orthogonal reactivity between traditional Pd catalysts, and the Rh catalysts employed, results in the ability to selectively activate either the C–S bond or C–X bond through catalyst choice. The Rh–bisphosphine catalyst has further been shown to be able to effect a hydroacylation-Sonogashira tandem sequence, and in combination with further onward reactions has been used in the synthesis of heterocycles and polycyclic systems.

Graphical abstract: A rhodium-catalysed Sonogashira-type coupling exploiting C–S functionalisation: orthogonality with palladium-catalysed variants

Supplementary files

Article information

Article type
Communication
Submitted
04 Jan 2019
Accepted
25 Jan 2019
First published
14 Feb 2019
This article is Open Access
Creative Commons BY license

Chem. Commun., 2019,55, 2757-2760

A rhodium-catalysed Sonogashira-type coupling exploiting C–S functionalisation: orthogonality with palladium-catalysed variants

M. Arambasic, M. K. Majhail, R. N. Straker, J. D. Neuhaus and M. C. Willis, Chem. Commun., 2019, 55, 2757 DOI: 10.1039/C9CC00092E

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