Palladium-catalyzed acetalization/cyclization of enynones with alcohols: rapid access to functionalized dihaloalkenyl dihydrofurans

Herein, we report a straightforward method to access alkenyl dihydrofurans via palladium-catalyzed acetalization/annulation from conjugated enynones and alcohols. The reaction undergoes a 5-exo-dig cyclization process, with the formation of four new chemical bonds including two carbonhalogen bonds o...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-12, Vol.58 (1), p.1397-1391
Main Authors: Ma, Ruize, Chen, Yang, Fang, Songjia, Jiang, Huanfeng, Yang, Shaorong, Wu, Wanqing
Format: Article
Language:English
Subjects:
Alcohols
Chemical bonds
Chemical reactions
Palladium
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Summary:Herein, we report a straightforward method to access alkenyl dihydrofurans via palladium-catalyzed acetalization/annulation from conjugated enynones and alcohols. The reaction undergoes a 5-exo-dig cyclization process, with the formation of four new chemical bonds including two carbonhalogen bonds on the exocyclic alkenyl moiety. Preliminary mechanistic studies suggest that the haloalkyne generated in situ should be involved in this transformation. A novel Pd-catalyzed acetalization/cyclization of enynones and alcohols for the construction of dihaloalkenyl dihydrofuran derivatives is described.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc03949d