Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation

Fyfe, James W. B. and Fazakerley, Neal J. and Watson, Allan J. B. (2016) Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation. Angewandte Chemie International Edition. ISSN 1433-7851 (In Press)

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Abstract

Chemoselective Suzuki-Miyaura cross-coupling generally requires a designed deactivation of one nucleophile towards transmetallation. Here we show that boronic acids can be chemoselectively reacted in the presence of ostensibly equivalently reactive boronic acid pinacol (BPin) esters by kinetic discrimination during transmetallation. Simultaneous electrophile control allows sequential chemoselective cross-couplings in a single operation in the absence of protecting groups.

ORCID iDs

Fyfe, James W. B. ORCID logoORCID: https://orcid.org/0000-0001-8501-9197, Fazakerley, Neal J. and Watson, Allan J. B.;
  • Item type:Article
    ID code:58949
    Dates:
    Date
    Event
    2 December 2016
    Published
    2 December 2016
    Accepted
    Notes:This is the peer reviewed version of the following article: Fyfe, J. W. B., Fazakerley, N. J., & Watson, A. J. B. (2016). Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation. Angewandte Chemie International Edition, which will be published in final form at http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
    Keywords:multinucleophile systems, chemical synthesis, chemoselectivity, organoborons, arylboron nucleophiles, transmetallation, kinetic discrimination, Suzuki-Miyaura reaction, boron, cross-coupling, palladium, Chemistry, Chemistry(all)
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:05 Dec 2016 09:40
    Last modified:18 Mar 2023 04:00
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/58949
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