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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.
Original language | English |
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Article number | e202103728 |
Number of pages | 13 |
Journal | Chemistry - A European Journal |
Volume | 28 |
Issue number | 13 |
Early online date | 25 Jan 2022 |
DOIs | |
Publication status | Published - 1 Mar 2022 |
Keywords
- isoxazoline
- electrochemistry
- cycloaddition
- DFT
- electrochemical method
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