Synthesis of 3-CF3-4-acyl-substituted quinoline derivatives via a cascade reaction of nitrosoarenes and -CF3-1,3-enynes
ORGANIC CHEMISTRY FRONTIERS(2023)
Abstract
An unprecedented tandem strategy for the construction of an array of 3-CF3-4-acyl functionalized quinolines has been described from readily available nitrosoarenes and beta-CF3-1,3-enynes as starting materials by the combined use of Cu(OTf)(2) as a catalyst and DMAP as a base. This reaction proceeds via a sequential formation of C-N, C-O and C-C bonds and the steric hindrance effect of substituents (R-1) on the benzene ring of nitrosoarenes has a crucial impact on the reaction reactivity and site-selectivity. This cascade transformation features a novel annulation, easy C-H bond activation, readily available starting materials, good step-economy, good site-selectivity, generation of three new bonds and mild reaction conditions.
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