Electrochemical synthesis of isoxazolines : method and mechanism

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:11 Nov 2024 13:22
    URI:https://strathprints.strath.ac.uk/id/eprint/79471
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