Palladium-Catalyzed Hydrophosphination of Terminal Alkynes with Diphenylphosphine Oxide in the Presence of Tetraphenyldiphosphine Monoxide

Abstract

In this study, the Pd(OAc) 2 -catalyzed hydrophosphination of terminal alkynes was investigated in detail by using various diphosphines, which have a P−P bond, and the detailed mechanistic insights led to the successful development of a novel Pd-catalyzed hydrophosphination of terminal alkynes using Ph 2 P(O)H as both the phosphorus and hydrogen source. This catalytic transformation was successfully promoted in the presence of catalytic Ph 2 P(O)−PPh 2 , and the corresponding alkenylphosphine oxide was obtained in moderate to excellent yields with excellent product selectivity.

Iodine‐Catalyzed One‐pot Formation of Phosphorus‐Heteroatom Bonds from Stable Diphosphines in Air

“…[20] Based on this background, we have energetically developed straightforward synthetic methods of phosphorus-heteroatom compounds and their application to the functionalization of carbon-carbon unsaturated compounds via radical reactions and transition-metal-catalyzed reactions. [21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36] In particular, we have found that diphosphines containing phosphorusphosphorus single bonds can efficiently react with organic dichalcogenides to form the corresponding phosphorus-chalcogen interelement compounds. [32] Among a variety of diphosphines, tetraphenyldiphosphine disulfide, Ph 2 P(S)-P(S)Ph 2 1, is quite stable to air and moisture.…”