C–H heteroarylation of aromatics via catalyst free SN2′ coupling cycloaromatization

Abstract

The construction of a carbon–carbon bond is the most fundamental aspect of synthetic chemistry. In this study, we developed a catalyst-free S_N2′ reaction of β-OTf-substituted enamides with aromatics to obtain aryl-substituted aza-1,4-dicarbonyl compounds that can be in situ transformed into aryl-imidazole, aryl-thiazole, and aryl-oxazole in one-pot operation, thus achieving C–H heteroarylation of aromatics. This simple, efficient, clean and scalable strategy, which provides difficult-to-realize biaryl products, is compatible with various aromatics having varying complexities. This method can be used for the late-stage modification of various commercial pharmaceuticals or functional materials and offers an orthogonal approach for constructing biaryl compounds.