The mechanochemical production of biphenyls from nitrogen-containing organic compounds: amides, anilines, and sulfonamides

Abstract

The presence of C(sp²)–NH₂ in pharmaceutical building blocks provokes a pressing demand for the discovery and development of techniques for the deaminative functionalization of the C(sp²)–NH₂ moiety to enable new routes for the late-stage functionalization of complex molecules. In this work, we disclose the mechanochemical deaminative arylation of C(sp²)–NH₂ by the in situ conversion of C(sp²)–NH₂ to reactive pyridinium salts via the selective condensation of C(sp²)–NH₂ with pyrylium tetrafluoroborate. The deaminative coupling of anilines, amides, and sulfonamides represents a significant advancement for selective functionalization, enabling the production of precursor biphenyl compounds with potential for developing biologically active molecules.