Construction of trifluoromethyl-substituted enaminones via rhodium(III)-catalyzed aldehydic C(sp2)–H bond activation of N-sulfonyl-2-aminobenzaldehydes with CF3-imidoyl sulfoxonium ylides

Abstract

A rhodium (III)-catalyzed C (sp²)–H bond activation reaction of N-sulfonyl-2-aminobenzaldehydes with CF₃-imidoyl sulfoxonium ylides (TFISYs) has been achieved, which offers a facile and straightforward access to trifluoromethyl-substituted enaminones in moderate to excellent yields. The reaction involves a cascade aldehydic C (sp²)–H bond imidoylmethylation and imine-enamine tautomerization sequence. The obtained α–CF₃–enaminone products can act as versatile trifluoromethyl-containing synthons to construct a series of structurally diverse fluorinated heterocycles.