Synthesis of Cu super(I) Trifluoromethylselenates for Trifluoromethylselenolation of Aryl and Alkyl Halides

The development of new strategies for synthesis of trifluoromethylthiolate compounds is of considerable importance in pharmaceuticals, agrochemicals, and advanced materials. Accordingly, currently much attention is being devoted to the development of effective methods and reagents for their synthesis. In contrast, considerably less effort has been afforded to the development of preparing C-SeCF sub(3) bonds. Herein we report a concise route to synthesize a family of copper(I) trifluoromethylselenolate reagents by the reaction of CuI with the Ruppert's reagent (Me sub(3)SiCF sub(3)), KF, and elemental selenium in the presence of dinitrogen ligands in CH sub(3)CN at room temperature. The reagent [Cu(bpy)(SeCF sub(3))] sub(2) was proven to be air-stable and highly efficient for nucleophilic trifluoromethylthselenolation of a broad range of (hetero)aryl halides and alkyl halides. This method represents a powerful protocol for the construction trifluoromethylselenolate compounds. Keep it in the family! A family of copper(I) trifluoromethylselenolate complexes ligated by dinitrogen ligands have been synthesized from a mixture of CuI with Me sub(3)SiCF sub(3), Se, and KF at room temperature (see scheme). The complex ligated by bipyridine (bpy) proved to be a useful reagent for nucleophilic trifluoromethylselenolation of aryl halides and alkyl halides.