90550-19-9Relevant academic research and scientific papers
Nickel-Catalyzed Alkyl-Alkyl Cross-Couplings of Fluorinated Secondary Electrophiles: A General Approach to the Synthesis of Compounds having a Perfluoroalkyl Substituent
Liang, Yufan,Fu, Gregory C.
, p. 9047 - 9051 (2015/08/03)
Fluorinated organic molecules are of interest in fields ranging from medicinal chemistry to polymer science. Described herein is a mild, convenient, and versatile method for the synthesis of compounds bearing a perfluoroalkyl group attached to a tertiary carbon atom by using an alkyl-alkyl cross-coupling. A nickel catalyst derived from NiCl2 glyme and a pybox ligand achieves the coupling of a wide range of fluorinated alkyl halides with alkylzinc reagents at room temperature. A broad array of functional groups is compatible with the reaction conditions, and highly selective couplings can be achieved on the basis of differing levels of fluorination. A mechanistic investigation has established that the presence of 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) inhibits cross-coupling under these conditions and that a TEMPO-electrophile adduct can be isolated.
Dehydrogenation of perfluoroalkyl ketones by using a recyclable oxoammonium salt
Hamlin, Trevor A.,Kelly, Christopher B.,Leadbeater, Nicholas E.
supporting information, p. 3658 - 3661 (2013/07/19)
A novel dehydrogenation reaction of perfluoroalkyl ketones by the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (4-NHAc-TEMPO+BF4-, Bobbitt's salt, 1) is described. The reaction proceeds under mildly basic conditions and appears to be unique to perfluoroalkyl ketones. A proposed mechanism for this unusual transformation is given. The byproduct of the reaction, 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinyloxy (1a), can easily be recovered and used to regenerate the oxoammonium salt. The dehydrogenation of perfluoroalkyl ketones by using an oxoammonium salt is reported. The reaction proceeds under mildly basic conditions and affords α,β-unsaturated products in fair to excellent yields. The reaction likely proceeds through a two-step sequence. The spent oxidant can easily be recovered and used to regenerate the oxoammonium salt. Copyright
THE SYNTHESIS OF OPTICALLY ACTIVE BUILDING BLOCKS CARRYING AN α,α-DIHALOGENO-β,β,β-TRIFLUOROETHYL GROUP
Kitazume, Tomoya,Ohnogi, Takeshi,Lin, Jenq Tain
, p. 17 - 30 (2007/10/02)
Optically active molecules with α,α-dihalogeno-β,β,β-trifluoroethyl groups were prepared by the microbial hydrolysis of the corresponding esters.
DIASTEREOSELECTIVE REDUCTION OF PERFLUOROALKYLATED α,β-UNSATURATED KETONES WITH BAKER'S YEAST
Kitazume, Tomoya,Ishikawa, Nobuo
, p. 587 - 590 (2007/10/02)
The differentiation of a fluorinated group in the molecule with active fermenting yeast and the double asymmetric induction in some perfluoroalkylated α,β-unsaturated ketones are described.
