Transition-metal-mediated trifluoromethylselenolation reactions with diverse SeCF3 reagents

Advances in organometallic chemistry have accelerated the development of efficient transition-metal-mediated fluorination and fluoroalkylation reactions. These fluorinated functionalities can tremendously alter the physicochemical and biological properties of the parent organic molecules. In recent years, SeCF3-containing compounds have attracted increasing attention due to the unique stereoelectronic characteristics of the SeCF3 moiety and its potential applications in various fields. Transition-metal-mediated trifluoromethylselenolation using different SeCF3 reagents has become one of the most important methods to build SeCF3-containing molecules. It has been demonstrated that (1) copper complexes are, in particular, favoured for their broad substrate scope, low cost, and ability to stabilise the [SeCF3]− anion in diverse trifluoromethylselenolation; (2) palladium catalysts excel in Csp2–X and Csp2–H trifluoromethylselenolation; (3) silver salts show promise in Csp3–H trifluoromethylselenolation and trifluoromethylselenolative alkyne addition; (4) iron salts mainly act as Lewis acids or reductants; and (5) nickel and gold catalysts are mostly used for trifluoromethylselenolation of organic (pseudo)halides. This chapter fully reviews the progress in transition-metal-mediated trifluoromethylselenolation reactions using different SeCF3 reagents and aims to provide a clear framework for understanding the roles of transition metals and the reagent-substrate compatibility in these reactions.