Transition metal-free domino aryl-aryl coupling/phospha-Michael addition of diarylphosphinite to α,β-unsaturated ketones triggered by alkaline hydrolysis of (4-(2-alkenoyl)phenyl)triarylphosphonium salts

Abstract

Abstract Alkaline hydrolysis of a variety of (4-(2-alkenoyl)phenyl)triarylphosphonium bromides is reported. This hydrolysis triggers coupling of 4-(2-alkenoyl)phenyl with one aryl via phosphorus(V). Both diarylphosphinite and an α,β-unsaturated ketone are in situ generated and then undergo phospha-Michael addition to provide β-diarylphosphoryl ketones bearing a biaryl moiety in 27–70% yields in the absence of a transition metal. Graphical Abstract