Experimental and computational insights into the mechanism of the copper(I)-catalysed sulfonylative Suzuki-Miyaura reaction

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Hall, Callum G. J. and Sneddon, Helen F. and Pogány, Peter and Lindsay, David M. and Kerr, William J. (2023) Experimental and computational insights into the mechanism of the copper(I)-catalysed sulfonylative Suzuki-Miyaura reaction. Chemical Science, 14 (24). pp. 6738-6755. ISSN 2041-6539 (https://doi.org/10.1039/D3SC01337E)

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Abstract

A mechanistic study into the copper(I)-catalysed sulfonylative Suzuki-Miyaura reaction, incorporating sulfur dioxide, is described. Utilising spectroscopic and computational techniques, an exploration into the individual components of the competing catalytic cycles is delineated, including identification of the resting state catalyst, transmetalation of arylboronic acid onto copper(I), the sulfur dioxide insertion process, and the oxidative addition of aryl halide to CuI. Studies also investigated prominent side-reactions which were uncovered, including a competing copper(II)-catalysed mechanism. This led to an additional proposed and connected CuI/CuII/CuIII catalytic cycle to account for by-product formation.

ORCID iDs

Hall, Callum G. J., Sneddon, Helen F., Pogány, Peter, Lindsay, David M. ORCID logoORCID: https://orcid.org/0000-0003-4498-5094 and Kerr, William J. ORCID logoORCID: https://orcid.org/0000-0002-1332-785X;
  • Item type:Article
    ID code:85644
    Dates:
    Date
    Event
    28 June 2023
    Published
    31 May 2023
    Published Online
    30 May 2023
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:01 Jun 2023 08:28
    Last modified:12 Dec 2024 14:46
    URI:https://strathprints.strath.ac.uk/id/eprint/85644
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