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A Primary Acyl Phosphine Stabilized by a Phosphonium Ylide
Author(s) -
Petrone David A.,
Szkop Kevin M.,
Miao Linkun,
St. Onge Piers,
Qu ZhengWang,
Grimme Stefan,
Stephan Douglas W.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202106846
Subject(s) - ylide , chemistry , phosphonium , deprotonation , phosphine , primary (astronomy) , heteroatom , medicinal chemistry , organic chemistry , ion , catalysis , ring (chemistry) , physics , astronomy
Abstract Primary acyl‐phosphines are scarce in the literature. Here we show that the reaction of Ph 3 GePCO with the ylide Ph 3 PCH 2 proceeds to give the species Ph 3 PCHC(O)PH(GePh 3 ) 1 . Deprotonation of 1 with Na[N(SiMe 3 ) 2 ] generates the salt [Na(THF) 2 ][Ph 3 PCHC(O)P(GePh 3 )] 2 which provides subsequent access to the bis ‐germanylated acylphosphine, Ph 3 PCHC(O)P(GePh 3 ) 2 3 . Alternatively, treatment of 1 with HCl in dioxane affords the primary acylphosphine Ph 3 PCHC(O)PH 2 4 . 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.