Recent Progress Toward Trifluoromethylselenolation Reactions

Recently, a great deal of work has been done in the construction of C-CF3 or C-SCF3 bonds, because these fluorine groups display remarkable biological properties. Despite a trifluoromethylseleno group like CF3 or SCF3 may also have potential biological activity, the work on the construction of the C-SeCF3 bond is rarely reported. This mini-review highlights recent developments in trifluoromethylselenolation reactions using fluorine reagents, such as (Me4N)SeCF3, ClSeCF3, [(bpy)Cu(SeCF3)] 2, Me3SiCF3, and HCF3. Five approaches to the trifluoromethylselenolation of organic compounds are summarized: (1) trifluoromethylselenolation of aryl, alkyl, and heteroaryl halides, aromatic compounds, and boronic acids; (2) trifluoromethylselenolation of terminal alkynes and propargylic chlorides; (3) trifluoromethylselenolation of allylic bromides, vinyl halides, alpha-bromo-alpha,beta-unsaturated carbonyl compounds, and acyl chlorides; (4) trifluoromethylselenolation of diazo compounds; and (5) synthesis of trifluoromethyl selenides from selenocyanates and fluoroform.