Radical Trifluoroacetylation of Alkenes Triggered by a Visible-Light-Promoted C-O Bond Fragmentation of Trifluoroacetic Anhydride.
late-stage functionalization
organofluorine compounds
photoredox
radical mechanisms
radical trifluoroacetylation
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
04 10 2021
04 10 2021
Historique:
received:
12
07
2021
pubmed:
22
7
2021
medline:
22
7
2021
entrez:
21
7
2021
Statut:
ppublish
Résumé
We report a mild and operationally simple trifluoroacylation strategy of olefines, that utilizes trifluoroacetic anhydride as a low-cost and readily available reagent. This light-mediated process is fundamentally different from conventional methodologies and occurs through a trifluoroacyl radical mechanism promoted by a photocatalyst, which triggers a C-O bond fragmentation. Mechanistic studies (kinetic isotope effects, spectroelectrochemistry, optical spectroscopy, theoretical investigations) highlight the evidence of a fleeting CF
Identifiants
pubmed: 34289531
doi: 10.1002/anie.202109235
pmc: PMC8518413
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
22487-22495Informations de copyright
© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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