Copper-catalyzed synthesis of 2,2,2-trifluoroethyl selenoethers and their insecticidal activities

A simple and efficient protocol for the copper-catalyzed synthesis of aryl or alkyl 2,2,2-trifluoroethyl selenoethers has been developed. This reaction proceeded smoothly in the presence of CuI/phen as the catalyst, with elemental selenium, 1,1,1-trifluoro-2-iodoethane, and NaBH4 as reagents in DMF with a broad scope of functionalized (hetero)aryl or alkyl halides. Different functional groups were tolerated and moderate to excellent yields of 2,2,2-trifluoroethyl selenoethers were obtained. Some of the synthesized compounds exhibited promising insecticidal activities.