Electrochemical Synthesis of Isoxazolines: Method and Mechanism.
density functional calculations
electrochemistry
isoxazoline
mechanisms
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
01 Mar 2022
01 Mar 2022
Historique:
received:
03
02
2022
pubmed:
26
1
2022
medline:
3
3
2022
entrez:
25
1
2022
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 35076117
doi: 10.1002/chem.202103728
pmc: PMC9303936
doi:
Substances chimiques
Alkenes
0
Isoxazoles
0
Oximes
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202103728Subventions
Organisme : Engineering and Physical Sciences Research Council
ID : EP/S035990/1
Organisme : Leverhulme Trust
ID : ECF2016264
Informations de copyright
© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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