Visible-light-induced dehydrogenative β-trifluoromethylthiolation of tertiary amines and direct β-trifluoromethylthiolation of enamides

Facilitated by electron donor-acceptor complexes, an efficient dehydrogenative beta-trifluoromethylthiolation of tertiary amines with N-trifluoromethylthiophthalimide is presented under transition-metal-free, external oxidant-free, photocatalyst-free and mild reaction conditions. This protocol accommodates a range of substituted piperidines, as well as seven- and eight-membered saturated heterocycles. Additionally, employing this photocatalyst-free approach, direct beta-trifluoromethylthiolation of electron-rich enamides was also achieved through the involvement of a photoactive electron donor-acceptor (EDA) complex. The synthesis of beta-trifluoromethylthiolation enamines and beta-trifluoromethylthiolation enamides was realized involving an EDA photochemistry strategy.

Automated summary

This study presents an efficient reaction method for the dehydrogenative beta-trifluoromethylthiolation of tertiary amines with N-trifluoromethylthiophthalimide. The reaction is performed under transition-metal-free, external oxidant-free, photocatalyst-free and mild reaction conditions. The study also demonstrates the direct beta-trifluoromethylthiolation of electron-rich enamides using a photoactive electron donor-acceptor (EDA) complex.