Speciation control during Suzuki-Miyaura cross-coupling of haloaryl and haloalkenyl MIDA boronic esters

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Fyfe, James W. B. and Valverde, Elena and Seath, Ciaran P. and Kennedy, Alan R. and Redmond, Joanna M. and Anderson, Niall A. and Watson, Allan J. B. (2015) Speciation control during Suzuki-Miyaura cross-coupling of haloaryl and haloalkenyl MIDA boronic esters. Chemistry - A European Journal, 21 (24). 8951–8964. ISSN 1521-3765 (https://doi.org/10.1002/chem.201500970)

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Abstract

Boronic acid solution speciation can be controlled during the Suzuki-Miyaura cross-coupling of haloaryl MIDA boronic esters to enable the formal homologation of boronic acid derivatives. The reaction is contingent upon control of the basic biphase and is thermodynamically driven: temperature control provides highly chemoselective access to either BMIDA adducts at room temperature or BPin products at elevated temperature. Control experiments and solubility analyses have provided some insight into the mechanistic operation of the formal homologation process.

ORCID iDs

Fyfe, James W. B. ORCID logoORCID: https://orcid.org/0000-0001-8501-9197, Valverde, Elena, Seath, Ciaran P. ORCID logoORCID: https://orcid.org/0000-0002-6774-128X, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Redmond, Joanna M., Anderson, Niall A. and Watson, Allan J. B.;
  • Item type:Article
    ID code:53424
    Dates:
    Date
    Event
    8 June 2015
    Published
    8 May 2015
    Published Online
    8 April 2015
    Accepted
    Notes:This is the peer reviewed version of the following article: Fyfe, J. W. B., Valverde, E., Seath, C. P., Kennedy, A. R., Redmond, J. M., Anderson, N. A., & Watson, A. J. B. (2015). Speciation control during Suzuki-Miyaura cross-coupling of haloaryl and haloalkenyl MIDA boronic esters. Chemistry - A European Journal, 21(24), 8951–8964, which has been published in final form at http://dx.doi.org/10.1002/chem.201500970 This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:18 Jun 2015 14:19
    Last modified:12 Dec 2024 03:25
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/53424
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