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Issue 19, 2019
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A rhodium-catalysed Sonogashira-type coupling exploiting C–S functionalisation: orthogonality with palladium-catalysed variants

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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

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Publication details

The article was received on 04 Jan 2019, accepted on 25 Jan 2019 and first published on 14 Feb 2019


Article type: Communication
DOI: 10.1039/C9CC00092E
Citation: Chem. Commun., 2019,55, 2757-2760
  • Open access: Creative Commons BY license
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    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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