期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 28, 期 13, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202103728
关键词
density functional calculations; electrochemistry; isoxazoline; mechanisms
资金
- Strathclyde-GlaxoSmithKline (GSK) Doctoral Training partnership
- Leverhulme Trust
- EPRSC [EP/S035990/1]
An electrochemical method for the synthesis of substituted isoxazoline cores is presented, which can efficiently convert both aryl and alkyl aldoximes. In-situ reaction monitoring and theoretical calculations support the mechanism and reaction pathway.
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.
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