Homologation of aryl ketones to long-chain ketones and aldehydes via C-C bond cleavage.
Chemistry
Organic chemistry
Organic synthesis
Journal
iScience
ISSN: 2589-0042
Titre abrégé: iScience
Pays: United States
ID NLM: 101724038
Informations de publication
Date de publication:
15 Jul 2022
15 Jul 2022
Historique:
received:
12
02
2022
revised:
26
04
2022
accepted:
27
05
2022
entrez:
20
6
2022
pubmed:
21
6
2022
medline:
21
6
2022
Statut:
epublish
Résumé
Transition metal-catalyzed C-C bond cleavage is a powerful tool for the reconstruction of a molecular skeleton. We report herein the multi-carbon homologation of aryl ketones to long-chain ketones and aldehydes via ligand-promoted Ar-C(O) bond cleavage and subsequent cross coupling with alkenols. Various (hetero)aryl ketones are compatible in the reaction, affording the corresponding products wtih good to excellent yields with high regioselectivity. Further applications in the late-stage diversification of biologically important molecules demonstrate the synthetic utility of this protocol. Mechanistic studies indicate that the ligand plays an important role in both C-C bond cleavage and the asymmetric migration-insertion process.
Identifiants
pubmed: 35720269
doi: 10.1016/j.isci.2022.104505
pii: S2589-0042(22)00776-3
pmc: PMC9204744
doi:
Types de publication
Journal Article
Langues
eng
Pagination
104505Informations de copyright
© 2022 The Author(s).
Déclaration de conflit d'intérêts
The authors declare no competing interests.
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