Deoxygenative trifluoromethylthiolation of carboxylic acids.
Journal
Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951
Informations de publication
Date de publication:
07 Nov 2019
07 Nov 2019
Historique:
received:
09
07
2019
accepted:
26
08
2019
entrez:
15
2
2020
pubmed:
15
2
2020
medline:
15
2
2020
Statut:
epublish
Résumé
Here we describe a deoxygenative trifluoromethylthiolation method that yields trifluoromethyl thioesters from readily available carboxylic acids. The method is built upon an "umpolung" strategy where triphenylphosphine is used to first activate an electrophilic trifluoromethylthiolating reagent and then serves as an oxygen acceptor for the deoxygenation. The method is mild, efficient, broad-scope, and tolerant. It can be applied for the late-stage functionalization of numerous natural products and drug molecules containing a carboxylic acid group. The trifluoromethyl thioesters can be converted into trifluoromethyl thioethers by Pd-catalyzed decarbonylation.
Identifiants
pubmed: 32055327
doi: 10.1039/c9sc03396c
pii: c9sc03396c
pmc: PMC6979494
doi:
Types de publication
Journal Article
Langues
eng
Pagination
9555-9559Informations de copyright
This journal is © The Royal Society of Chemistry 2019.
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