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Electrochemical Synthesis of Isoxazolines: Method and Mechanism.

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.

SUBMITTER: Holman SDL

PROVIDER: S-EPMC9303936 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature

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Electrochemical Synthesis of Isoxazolines: Method and Mechanism.

Holman Samuel D L SDL Wills Alfie G AG Fazakerley Neal J NJ Poole Darren L DL Coe Diane M DM Berlouis Leonard A LA Reid Marc M

Chemistry (Weinheim an der Bergstrasse, Germany) 20220210 13

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 ki ...[more]

PMID: 35076117

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