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