A Primary Acyl Phosphine Stabilized by a Phosphonium Ylide.

Petrone, David A.; Szkop, Kevin M.; Miao, Linkun; St. Onge, Piers; Qu, Zheng‐Wang; Grimme, Stefan; Stephan, Douglas W.

Primary acyl‐phosphines are scarce in the literature. Here we show that the reaction of Ph3GePCO with the ylide Ph3PCH2 proceeds to give the species Ph3PCHC(O)PH(GePh3) 1. Deprotonation of 1 with Na[N(SiMe3)2] generates the salt [Na(THF)2][Ph3PCHC(O)P(GePh3)] 2 which provides subsequent access to the bis‐germanylated acylphosphine, Ph3PCHC(O)P(GePh3)23. Alternatively, treatment of 1 with HCl in dioxane affords the primary acylphosphine Ph3PCHC(O)PH24. Compound 4 is a rare example of an air stable primary acyl‐phosphines and the first devoid of a stabilizing heteroatom adjacent to the carbonyl fragment.

PHOSPHINE; PROTON transfer reactions; DIOXANE; PHOSPHINES; BETAINE

Angewandte Chemie, 2021, Vol 133, Issue 34, p18695

0044-8249

Academic Journal

10.1002/ange.202106846