105993-90-6Relevant articles and documents
Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents
Geaneotes, Paul,Guo, Rui,Liu, Peng,Qi, Xiaotian,Wang, Ruihan,Wang, Yi-Ming,Xiang, Hengye
, p. 16651 - 16660 (2020)
The discovery of safe, general, and practical procedures to prepare vinyl fluorides from readily available precursors remains a synthetic challenge. The metal-free hydrofluorination of alkynes constitutes an attractive though elusive strategy for their preparation. Introduced here is an inexpensive and easily handled reagent that enables the development of simple and scalable protocols for the regioselective hydrofluorination of alkynes to access both the E and Z isomers of vinyl fluorides. These reaction conditions were suitable for a diverse collection of alkynes, including several highly functionalized pharmaceutical derivatives. Computational and experimental mechanistic studies support C?F bond formation through vinyl cation intermediates, with the E- and Z-hydrofluorination products forming under kinetic and thermodynamic control, respectively.
Solvent- A nd anion-dependent rearrangement of fluorinated carbene ligands provides access to fluorinated alkenes
Hall, Lewis M.,Milner, Lucy M.,Hart, Sam J.,Whitwood, Adrian C.,Lynam, Jason M.,Slattery, John M.
supporting information, p. 17655 - 17659 (2019/12/23)
The construction of fluorocarbene ligands within the coordination sphere of transition metal complexes using sequential nucleophilic and electrophilic addition to a vinylidene complex is described. Reaction of [Ru(η5-C5H5)(dppe)(CCPhF)][N(SO2Ph)2] with [NMe4]F results in nucleophilic attack of fluoride at the metal-bound carbon of the vinylidene ligand to give alkenyl complex [Ru(η5-C5H5)(dppe)(-CFCFPh)]. Subsequent eletrophilic fluorination with N-fluorobenzenesulfonimide (NFSI) results in the formation of the fluorinated carbene complex [Ru(η5-C5H5)(dppe)(CF-CHFPh)][N(SO2Ph)2]. The fluorocarbene complexes undergo rearrangement to liberate free fluorinated alkenes, a process governed by the choice of solvent and anion, representing a new metal-mediated route to fluorinated alkenes from alkynes.
SYNTHESE DE CHLOROFLUOROVINYLSILANES ET DE QUELQUES DERIVES
Martin, Sophie,Sauvetre, Raymond,Normant, Jean-F.
, p. 317 - 320 (2007/10/02)
Several chlorofluoroolefins were prepared from 1,1-dichloro-2,2-difluoroethylene via chlorofluorovinylsilanes.