Direct Synthesis of Triarylethynylphosphines from White Phosphorus and Arylacetylidene Lithiums

A novel diphenyl diselenide-mediated protocol for the direct synthesis of triarylethynylphosphines from white phosphorus and arylalkynyl lithiums is presented. Employing diphenyl diselenide as the mediator, a catalytic amount of arylalkynyl lithiums activates P4 to generate triarylselenophosphine intermediates. Subsequent stoichiometric coupling with arylalkynyl lithiums affords the target triarylethynylphosphines. The transformation proceeds efficiently under ambient conditions using commercially available materials, obviating toxic chlorination steps. The protocol exhibits a broad substrate scope, successfully incorporating diverse arenes and heterocycles such as naphthalene, anthracene, phenanthrene, thiophene, and ferrocene.