Electrochemical synthesis of isoxazolines : method and mechanism

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Holman, Samuel D. L. and Wills, Alfie G. and Fazakerley, Neal J. and Poole, Darren L. and Coe, Diane M. and Berlouis, Leonard and Reid, Marc (2022) Electrochemical synthesis of isoxazolines : method and mechanism. Chemistry - A European Journal, 28 (13). e202103728. ISSN 1521-3765 (https://doi.org/10.1002/chem.202103728)

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Abstract

An electrochemical method for the green and practical synthesis of a broad range of substituted isoxazoline cores is presented. Both aryl and more challenging alkyl aldoximes are converted to the desired isoxazoline in an electrochemically enabled regio- and diastereoselective reaction with electron-deficient alkenes. Additionally, in-situ reaction monitoring methods compatible with electrochemistry equipment have been developed in order to probe the reaction pathway. Supporting analyses from kinetic (time-course) modelling and density functional theory support a stepwise, radical-mediated mechanism, and discounts hypothesised involvement of closed shell [3+2] cycloaddition pathways.

ORCID iDs

Holman, Samuel D. L., Wills, Alfie G., Fazakerley, Neal J., Poole, Darren L., Coe, Diane M., Berlouis, Leonard ORCID logoORCID: https://orcid.org/0000-0002-7217-1680 and Reid, Marc ORCID logoORCID: https://orcid.org/0000-0003-4394-3132;
  • Item type:Article
    ID code:79471
    Dates:
    Date
    Event
    1 March 2022
    Published
    25 January 2022
    Published Online
    25 January 2022
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:04 Feb 2022 10:06
    Last modified:21 Nov 2024 05:37
    URI:https://strathprints.strath.ac.uk/id/eprint/79471
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