Palladium-catalyzed allylic alkylation dearomatization of β-naphthols and indoles with gem-difluorinated cyclopropanes

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.

Automated summary

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.