CuBr2-mediated dehydrogenative [4+2] annulation of 1-naphthyl-1,3-indandiones and alkenes

Intermolecular annulation reactions of 1-naphthyl-1,3-indandiones with alkenes proceed efficiently in the presence of a copper catalyst to generate spirocarbocycle compounds. Various spirocyclic molecules bearing an all-carbon quaternary center could be obtained by this novel method with good yields...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2024-08, Vol.60 (68), p.9070-9073
Main Authors: Zhang, Xu, Chang, Mengfan, Ni, Tongtong, Liu, Shuhan, Li, Wenguang, Xu, Xuefeng
Format: Article
Language:English
Subjects:
Alkenes
Chemical reactions
Copper bromide
Dehydrogenation
Functional groups
Organic chemistry
Regioselectivity
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Summary:Intermolecular annulation reactions of 1-naphthyl-1,3-indandiones with alkenes proceed efficiently in the presence of a copper catalyst to generate spirocarbocycle compounds. Various spirocyclic molecules bearing an all-carbon quaternary center could be obtained by this novel method with good yields, excellent regioselectivity, and good functional group tolerance. A radical mechanism is proposed based on the HRMS analysis results of control experiments.
ISSN:1359-7345
1364-548X
DOI:10.1039/d4cc02386b