457-49-8Relevant academic research and scientific papers
Stereoconvergent negishi arylations of racemic secondary alkyl electrophiles: Differentiating between a CF3 and an alkyl group
Liang, Yufan,Fu, Gregory C.
supporting information, p. 9523 - 9526 (2015/08/18)
In this report, we establish that a readily available nickel/bis(oxazoline) catalyst accomplishes a wide array of enantioconvergent cross-couplings of arylzinc reagents with CF3-substituted racemic secondary alkyl halides, a process that necessitates that the chiral catalyst be able to effectively distinguish between a CF3 and an alkyl group in order to provide good ee. We further demonstrate that this method can be applied without modification to the catalytic asymmetric synthesis of other families of fluorinated organic compounds.
A Weinreb amide approach to the synthesis of trifluoromethylketones
Rudzinski, Diandra M.,Kelly, Christopher B.,Leadbeater, Nicholas E.
supporting information, p. 9610 - 9612 (2012/10/29)
A novel route to access trifluoromethylketones (TFMKs) from Weinreb amides is reported. This represents the first documented case of the Ruppert-Prakash reagent (TMS-CF3) reacting in a constructive manner with an amide and enables synthesis of TMFKs without risk of over-trifluoromethylation.
Oxidation of α-trifluoromethyl alcohols using a recyclable oxoammonium salt
Kelly, Christopher B.,Mercadante, Michael A.,Hamlin, Trevor A.,Fletcher, Madison H.,Leadbeater, Nicholas E.
, p. 8131 - 8141 (2013/01/15)
A simple, mild method for the oxidation of α-trifluoromethyl alcohols to trifluoromethyl ketones (TFMKs) using the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) is described. Under basic conditions, oxidation proceeds rapidly and affords good to excellent yields of TFMKs, without concomitant formation of the hydrate. The byproduct of the oxidation, 4-acetylamino-2,2,6,6-tetramethyl-1- piperidinyloxy (1c), is easily recovered and can be conveniently reoxidized to regenerate the oxoammonium salt.
NOUVELLE SYNTHESE DE TRIFLUOROMETHYLCETONES ET D' α-BROMO TRIFLUOROMETHYLCETONES
Begue, J. P.,Mesureur, D.
, p. 271 - 282 (2007/10/02)
We report a new method for the preparation of trifluoromethylketones, as an alternative to the use of organometallics.The condensation of phosphonium ylides with trimethylsilyl trifluoroacetate provides silyloxy enol ethers whose hydrolysis leads to trifluoromethylketones.Bromation of the same silyloxy enol ether is also a convenient preparation of α-bromo trifluoromethylketone.
