Syntheses and Synthetic Applications of Functionalized Propargylic and Allylic Fluorides.
allylic fluoride
fluorinated heterocycles
organocatalysis
propargylic fluoride
transition-metal catalysis
Journal
Chemical record (New York, N.Y.)
ISSN: 1528-0691
Titre abrégé: Chem Rec
Pays: United States
ID NLM: 101085550
Informations de publication
Date de publication:
Sep 2023
Sep 2023
Historique:
revised:
25
02
2023
received:
20
01
2023
medline:
14
3
2023
pubmed:
14
3
2023
entrez:
13
3
2023
Statut:
ppublish
Résumé
This account presents the synthesis and application of propargylic and allylic fluorides containing hydroxy or carbonyl functional groups. In particular, the Barbier-type reaction of difluoropropargyl bromides with aldehydes or chloroformates provides versatile propargylic fluorides, and the organocatalytic fluorination of dienamine intermediates has been demonstrated as an effective method to obtain allylic fluorides stereoselectively. Additionally, mechanistic insights into such reactions are discussed with the aid of density functional theory calculations. The report also describes the preparation of fluorinated 1,7-diyne or 1,7-enyne derivatives of these compounds. These propargylic and allylic fluorides can be used as building blocks for fluorinated heterocycles, such as fluorinated furans, tetrahydrofurans, and lactams. Additionally, fluorinated bi- or tri-heterocyclic compounds can be synthesized via transition-metal-catalyzed reactions with fluorinated 1,7-diyne or 1,7-enyne derivatives.
Identifiants
pubmed: 36912721
doi: 10.1002/tcr.202300021
doi:
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300021Subventions
Organisme : JSPS KAKENHI
ID : 25810022
Informations de copyright
© 2023 The Chemical Society of Japan & Wiley-VCH GmbH.
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