Synthesis of Fulvene Vinyl Ethers by Gold Catalysis.
aryl cations
fulvene ethers
gold catalysis
vinyl cations
vinyl ethers
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
21 Apr 2020
21 Apr 2020
Historique:
received:
21
01
2020
revised:
23
02
2020
pubmed:
25
2
2020
medline:
25
2
2020
entrez:
25
2
2020
Statut:
ppublish
Résumé
Gold-catalyzed cyclization of 1,5-diynes with ketones as reagents and solvent provides diversely substituted vinyl ethers under mild conditions. The regioselectivity of such gold-catalyzed cyclizations is usually controlled by the scaffold of the diyne. Herein, we report the first solvent-controlled switching of regioselectivity from a 6-endo-dig- to 5-endo-dig-cyclization in these transformations, providing fulvene derivatives. With respect to the functional-group tolerance, aryl fluorides, chlorides, bromides, and ethers are tolerated. Furthermore, the mechanism and selectivity are put to scrutiny by experimental studies and a thermodynamic analysis of the product. Additionally, 6-(vinyloxy)fulvenes are a hitherto unknown class of compounds. Their reactivity is briefly evaluated, to give insights into their potential applications.
Identifiants
pubmed: 32092204
doi: 10.1002/chem.202000338
pmc: PMC7216831
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
5280-5287Subventions
Organisme : Brazilian Council for Scientific and Technological Development (CNPQ)
Informations de copyright
© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
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