Hydroxy-directed fluorination of remote unactivated C(sp
Journal
Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951
Informations de publication
Date de publication:
15 Jun 2022
15 Jun 2022
Historique:
received:
02
04
2022
accepted:
02
05
2022
entrez:
1
7
2022
pubmed:
2
7
2022
medline:
2
7
2022
Statut:
epublish
Résumé
We report a photochemically induced, hydroxy-directed fluorination that addresses the prevailing challenge of high diastereoselectivity in this burgeoning field. Numerous simple and complex motifs showcase a spectrum of regio- and stereochemical outcomes based on the configuration of the hydroxy group. Notable examples include a long-sought switch in the selectivity of the refractory sclareolide core, an override of benzylic fluorination, and a rare case of 3,3'-difluorination. Furthermore, calculations illuminate a low barrier transition state for fluorination, supporting our notion that alcohols are engaged in coordinated reagent direction. A hydrogen bonding interaction between the innate hydroxy directing group and fluorine is also highlighted for several substrates with
Identifiants
pubmed: 35774162
doi: 10.1039/d2sc01907h
pii: d2sc01907h
pmc: PMC9200124
doi:
Types de publication
Journal Article
Langues
eng
Pagination
7007-7013Informations de copyright
This journal is © The Royal Society of Chemistry.
Déclaration de conflit d'intérêts
The authors declare no competing financial interest.
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