Journal
CHEMICAL COMMUNICATIONS
Volume 57, Issue 10, Pages 1262-1265Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0cc07529a
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Funding
- National Natural Science Foundation of China [NSFC220 71267]
- Foundation of the Open Project of State Key Laboratory of Natural Medicines [SKLNMZZ202023, CPU2018GY35, CPU2018GY04]
- National Science AMP
- Technology Major Project Key New Drug Creation and Manufacturing Program, China [2020ZX09201015]
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The palladium-catalyzed allylic alkylation dearomatization reaction provides an efficient route to access compounds with naphthalene and indole moieties, featuring high yields and Z-selectivity. This reaction benefits from a wide substrate scope and good functional group tolerance, allowing for the synthesis of complex molecules with quaternary carbon centers.
A palladium-catalyzed allylic alkylation dearomatization of beta-naphthols and indoles with gem-difluorinated cyclopropanes has been developed. This reaction provided an efficient route to access 2-fluoroallylic beta-naphthalenones and indolenines bearing quaternary carbon centers in good yields with high Z-selectivity via C-C bond activation, C-F bond cleavage and the dearomatization process, benefiting from the wide substrate scope and good functional group tolerance. Moreover, 2-fluoroallylic furanoindoline and pyrroloindolines were achieved in good efficiency via cascade allylic alkylation, dearomatization and cyclization processes in the presence of Et3B.
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