Trifluoromethylselenofunctionalization of carbon-carbon multiple bonds have significantly expanded the synthetic toolbox for preparing vicinally functionalized CF3Se-containing compounds. This emerging methodology enables the efficient introduction of both the trifluoromethylseleno group and various functional moieties across double or triple bonds in a single step. In this review, we summarize recent advances in the trifluoromethylselenolation of alkenes and alkynes, categorizing these advancements based on the diverse functional groups introduced. Furthermore, we elucidate the mechanistic aspects of these reactions, which may inspire further research in this promising area of study.

Abstract

The incorporation of the trifluoromethylselenyl (CF₃Se) group has become a prominent area of research in recent years because of its high electron-withdrawing capacity, excellent lipophilicity, good stability, and favorable bioavailability. These properties make CF₃Se a promising structural motif for drug design and development. Among the various methods for synthesizing CF₃Se-containing compounds, trifluoromethylselenofunctionalization of unsaturated C─C bonds has emerged as a powerful strategy for the preparation of these compounds because this process facilitates the introduction of the CF₃Se motif as well as other functional groups into unsaturated C─C bonds. In this review, we summarize recent advancements and achievements in the trifluoromethylselenofunctionalization of multiple C─C bonds. For clarity, the reactions were classified according to the type of functional groups introduced. Additionally, this review highlights the mechanistic aspects of these reactions, which may inspire further work in this appealing research field.