Recent Advances in the Development of Direct Trifluoromethylselenolation Reagents and Methods

The introduction of trifluoromethylchalcogen group (CF3O, CF3S and CF3Se) has attracted growing attention in the field of modern organofluorine chemistry. Compared with the CF3S and CF3O chemistry, methods for trifluoromethylselenolation are much less developed owing to the limited availability of CF3Se transfer reagents and synthetic methods. The CF3Se group introduces promising lipophilicity (Hansch-Leo parameter=1.29) and strong electron-withdrawing effect (Hammett constants sigma(m)=0.44, sigma(p)=0.45) which are important parameters for the development of new pharmaceutically relevant compounds. Traditionally, the CF3Se compounds were synthesized by the nucleophilic trifluoromethylation of diselenides and selenocyanates, which suffered from harsh conditions and/or limited substrates scope. Compared with the indirect methods, the direct formation of C-SeCF3 constitutes is a more efficient approach. In recent years, new reagents and methods were developed which enabled the incorporation of the trifluoromethylselenyl group directly under mild conditions, specifically in transition metal catalysis and photoredox catalysis. In this review, we will focus on direct trifluoromethylselenolation strategies based on the development of new trifluoromethylselenolation reagents and methods.

Automated summary

The introduction of trifluoromethylselenolation has attracted attention for its attractive lipophilicity and strong electron-withdrawing effect, with direct formation of C-SeCF3 being more efficient compared to indirect methods.