Synthesis of Cu(I) trifluoromethylselenates for trifluoromethylselenolation of aryl and alkyl halides

• Published in: Chemistry : a European journal Vol. 20; no. 3; pp. 657 - 661
• Main Authors: Chen, Chaohuang, Ouyang, Li, Lin, Quanfu, Liu, Yanpin, Hou, Chuanqi, Yuan, Yaofeng, Weng, Zhiqiang
• Format: Journal Article
• Language: English
• Published: Germany 13.01.2014
• Subjects: CSe bonds; copper; cross coupling; trifluoromethylselenolation; complexes
• ISSN: 1521-3765
• DOI: 10.1002/chem.201303934

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SeCF3 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 (Me3 SiCF3 ), KF, and elemental selenium in the presence of dinitrogen ligands in CH3 CN at room temperature. The reagent [Cu(bpy)(SeCF3 )]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.