Visible-light-initiated catalyst-free trifluoromethylselenolation of arylsulfonium salts with [Me4N][SeCF3]

The redox potential gap between arylsulfonium salts and [Me4N][SeCF3] has been clearly revealed by CV measurements. Construction of the carbon-selenium bond by overcoming this gap without using catalysts and additives is a challenging task. In this work, we reported an efficient visible-light-induced cross-coupling of arylsulfonium triflate with [Me4N][SeCF3] by simply mixing these two species, which allowed the facile synthesis of various aryl trifluoromethyl selenoethers under catalyst- and additive-free conditions. The mechanistic study indicated that aryl and SeCF3 radicals might be formed as key intermediates in the reactions. Merits of the reactions include operational simplicity, high efficiency, visible-light irradiation, good functional group tolerance, a wide range of substrates, excellent chemoselectivity, and good yields of trifluoromethylselenolated products, which combined with a sulfenylation process enabled the selective and practical installation of SeCF3 moieties onto complex arenes including drug molecules via a formal C-H functionalization.

Automated summary

This study reported an efficient visible-light-induced cross-coupling reaction of arylsulfonium triflate with [Me4N][SeCF3] for the synthesis of various aryl trifluoromethyl selenoethers. The reaction exhibits operational simplicity, high efficiency, catalyst- and additive-free conditions, wide substrate scope, and good yields.