Vinyl cation-mediated intramolecular hydroarylation of alkynes using pyridinium reagents.
Journal
Chemical communications (Cambridge, England)
ISSN: 1364-548X
Titre abrégé: Chem Commun (Camb)
Pays: England
ID NLM: 9610838
Informations de publication
Date de publication:
13 Oct 2022
13 Oct 2022
Historique:
pubmed:
24
9
2022
medline:
15
10
2022
entrez:
23
9
2022
Statut:
epublish
Résumé
Once considered to be exotic species of limited synthetic utility, vinyl cations have recently been shown to be highly versatile intermediates in a variety of processes. Here, we report a method for the synthesis of aryl-substituted benzocycloheptenes and -hexenes using the hydrotriflate salt of an electron-poor pyridine as a uniquely efficient proton source for a vinyl cation mediated Friedel-Crafts cyclization. The mild conditions made possible by this reagent allowed a range of simple and functionalized alkynes bearing pendant aryl groups to serve as suitable substrates for this scalable and convenient protocol.
Identifiants
pubmed: 36149344
doi: 10.1039/d2cc03794g
pmc: PMC9588717
mid: NIHMS1836140
doi:
Substances chimiques
Alkynes
0
Cations
0
Indicators and Reagents
0
Protons
0
Pyridines
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
11523-11526Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM142945
Pays : United States
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