Synthesis of 3-CF3-4-acyl-substituted quinoline derivatives via a cascade reaction of nitrosoarenes and β-CF3-1,3-enynes

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 β-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 (R¹) 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.