197783-86-1Relevant academic research and scientific papers
CF2H, a Hydrogen Bond Donor
Sessler, Chanan D.,Rahm, Martin,Becker, Sabine,Goldberg, Jacob M.,Wang, Fang,Lippard, Stephen J.
, p. 9325 - 9332 (2017)
The CF2H group, a potential surrogate for the OH group, can act as an unusual hydrogen bond donor, as confirmed by crystallographic, spectroscopic, and computational methods. Here, we demonstrate the bioisosterism of the OH and CF2H
Direct Nucleophilic Difluoromethylation of Carbonyl Compounds
Deng, Zuyong,Lin, Jin-Hong,Cai, Ji,Xiao, Ji-Chang
supporting information, p. 3206 - 3209 (2016/07/14)
Phosphonium salt ([Ph3P+CF2H] Br-, DFPB) was found to be an efficient nucleophilic difluoromethylation reagent. Although DFPB is known as a phosphonium ylide precursor, its reaction with carbonyl compounds under traditional Wittig reaction conditions did not give the expected Wittig difluoroolefinated products, but afforded the nucleophilic difluoromethylation products, α-CF2H alcohols. Mechanistic investigation reveals that the unexpected transformation proceeded via the direct transfer of the CF2H group, which resulted from the high P-O affinity.
