Electron Donor-Acceptor Complex Initiated Photochemical Phosphorus Arylation with Diaryliodonium Salts toward the Synthesis of Phosphine Oxides

Arylation of amino-, diamino- and triaminophosphines with aryl(mesityl)iodonium triflates under blue light irradiation followed by oxidative P-N bond cleavage in the insitu generated amino phosphonium salts under hydrolytic conditions represent a method for the synthesis of substituted arylphosphine oxides, arylphosphinic and arylphosphonic amides respectively. The proposed approach is based on using visible light as the only promoter for the C-P bond formation, accommodates a variety of functional groups, and can be applied to the late-stage C-H functionalization of drug molecules.

Automated summary

Arylation of various phosphines with aryl(mesityl)iodonium triflates under blue light irradiation, followed by oxidative P-N bond cleavage in the in situ generated amino phosphonium salts under hydrolytic conditions, allows for the synthesis of substituted arylphosphine oxides, arylphosphinic, and arylphosphonic amides. This method utilizes visible light as the sole promoter for C-P bond formation, is compatible with a wide range of functional groups, and can be applied for late-stage C-H functionalization of drug molecules.