Photoinduced Trifluoromethyl- and Difluoromethyl-Chalcogenation of α-Diazo Compounds

Abstract

Organofluorides, including trifluoromethylthiolated compounds, play an important role in pharmaceuticals, agrochemicals and materials science. Although the synthesis of these organofluorides has been well studied, harsh conditions and specific substrates are usually involved, which limited the development of this field. Herein, we report a novel protocol to construct highly functionalized trifluoromethylthiolated and derived scaffolds via the trifluoromethyl- and difluoromethyl-chalcogenation of α-diazo compounds under mild and green conditions using a photochemical strategy. This multicomponent reaction exhibits broad substrate scope and good functional group tolerance (37 examples, up to >99% yield), which could be applied to late-stage modification of complex natural products. Additionally, the gram-scale synthesis and antibacterial assays were carried out to explore the application of this transformation, and the results showed good scalability (1.45 g, 69% yield) as well as promising antibacterial activity. Moreover, the mechanistic study indicates a cascade process via oxonium species.