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

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

Keywords:

• Alkaline hydrolysis
• aryl-aryl coupling
• phospha-Michael addition
• ligand coupling
• diarylphosphine oxide
• unsaturated ketone

Acknowledgment

We thank the National Natural Science Foundation of China for their financial support of our program (Grant No. 21272170).

Supporting information

Full experimental detail, and NMR spectra (¹H and ¹³C). This material can be found via the “Supplementary Content” section of this article’s webpage.