Facile preparation of SeCF3-substituted alkenes from alkenyl iodides and selenium powder

Abstract

Abstract A synthetic method of SeCF3-substituted alkenes by a copper-mediated trifluoromethylselenolation of alkenyl iodides has been developed. In the presence of CuI and bpy, AgSeCF3 generated in-situ from Ag salt, TMSCF3, and commercially available Se powder, can be successfully coupled with alkenyl iodides to produce the trifluoromethylselenoalkenes with high chemoselectivity. The reaction shows a broad substrate scope including alkenyl iodides derived from biologically active molecules. Moreover, the feasibility of its scale-up synthesis has been demonstrated, thereby underscoring the practicality of the protocol.