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Updated: Mar 2, 2026
Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
Published on: October 3, 2014
Direct Synthesis of Triarylethynylphosphines from White Phosphorus and Arylacetylidene Lithiums
Yu-Zhong Yang1, Yu Chen1, Xinlei Huangfu1,2
1Beijing National Laboratory for Molecular Sciences (BNLMS), State Key Laboratory of Rare-earth Materials Chemistry and Applications, Key Laboratory of Bioorganic Chemistry, and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
Abstract:
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.
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