Inhibition of (dppf)nickel-catalysed Suzuki-Miyaura cross-coupling reactions by α-halo-N-heterocycles

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Cooper, Alasdair K. and Greaves, Megan E. and Donohoe, William and Burton, Paul M. and Ronson, Thomas O. and Kennedy, Alan R. and Nelson, David J. (2021) Inhibition of (dppf)nickel-catalysed Suzuki-Miyaura cross-coupling reactions by α-halo-N-heterocycles. Chemical Science, 12 (42). pp. 14074-14082. ISSN 2041-6539 (https://doi.org/10.1039/D1SC04582B)

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Abstract

A nickel/dppf catalyst system was found to successfully achieve the Suzuki-Miyaura cross-coupling reactions of 3- and 4-chloropyridine and of 6-chloroquinoline but not of 2-chloropyridine or of other α-halo-N-heterocycles. Further investigations revealed that chloropyridines undergo rapid oxidative addition to [Ni(COD)(dppf)] but that α-halo-N-heterocycles lead to the formation of stable dimeric nickel species that are catalytically inactive in Suzuki-Miyaura cross-coupling reactions. However, the corresponding Kumada-Tamao-Corriu reactions all proceed readily, which is attributed to more rapid transmetalation of Grignard reagents.

ORCID iDs

Cooper, Alasdair K., Greaves, Megan E., Donohoe, William, Burton, Paul M., Ronson, Thomas O., Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015 and Nelson, David J. ORCID logoORCID: https://orcid.org/0000-0002-9461-5182;
  • Item type:Article
    ID code:78182
    Dates:
    Date
    Event
    14 November 2021
    Published
    11 October 2021
    Published Online
    10 October 2021
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:15 Oct 2021 09:20
    Last modified:11 Nov 2024 13:16
    URI:https://strathprints.strath.ac.uk/id/eprint/78182
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