CuF₂/DMAP-Catalyzed N-Vinylation: Scope and Mechanistic Study

Abstract

CuF₂/DMAP has been established as an excellent catalytic system for vinylsilane-promoted N-vinylation of amides and azoles at room temperature without an external fluoride source. A mechanism has been proposed on the basis of the isolation of reactive intermediate [Cu(DMAP)₄Cl₂], fluoride ion-assisted transmetalation, and ultraviolet-visible spectroscopic studies. The catalytic efficiency of the synthesized and structurally characterized [Cu(DMAP)₄Cl₂] complex has been demonstrated. The valuable monomers for water-soluble polymers, viz., NVP, NVC, and NVIBA, were synthesized on a gram scale.