Electrochemical synthesis of isoxazolines: method and mechanism

Samuel D. L. Holman, Alfie G. Wills, Neal J. Fazakerley, Darren L. Poole, Diane M. Coe, Leonard Berlouis, Marc Reid

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)
37 Downloads (Pure)

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.

Original languageEnglish
Article numbere202103728
Number of pages13
JournalChemistry - A European Journal
Volume28
Issue number13
Early online date25 Jan 2022
DOIs
Publication statusPublished - 1 Mar 2022

Keywords

  • isoxazoline
  • electrochemistry
  • cycloaddition
  • DFT
  • electrochemical method

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