80446-60-2

Upstream product

• 394-59-2 2,2,2-trifluoro-1-(p-tolyl)ethanone 
• 446-65-1 2,2,2-trifluoro-1-(4-methylphenyl)ethanol 
• 97-72-3 2-Methylpropionic anhydride 
• 104-87-0 4-methyl-benzaldehyde 
• 81290-20-2 (trifluoromethyl)trimethylsilane 

Relevant academic research and scientific papers

Asymmetric Hydrogenation of Aryl Perfluoroalkyl Ketones Catalyzed by Rhodium(III) Monohydride Complexes Bearing Josiphos Ligands

The asymmetric hydrogenation of 2,2,2-trifluoroacetophenones and aryl perfluoroalkyl ketones was developed using a unique, well-defined chloride-bridged dinuclear rhodium(III) complex bearing Josiphos-type diphosphine ligands. These complexes were prepared from [RhCl(cod)]2, Josiphos ligands, and hydrochloric acid. As catalyst precursors, they allow for the efficient and enantioselective synthesis (up to 99 % ee) of chiral secondary alcohols with perfluoroalkyl groups. This system does not require an activating base for the hydrogenation of 2,2,2-trifluoroacetophenones. Additionally, the enantioselective C=O hydrogenations of 2-phenyl-3-(haloacetyl)-indoles, a class of privileged structures in medicinal chemistry, is reported for the first time.

Catalytic asymmetric β-hydrogen transfer reduction of α-trifluoromethyl aromatic ketones with diethylzinc

Abstract The catalytic asymmetric β-hydrogen transfer reduction of α-trifluoromethyl ketones using diethylzinc as the β-hydrogen donor was developed with the use of phosphinamide chiral ligand. The corresponding alcohol products were afforded in good yields with up to 73% ee. This method was successfully applied to the chemo- and enantioselective reduction of α-methyl/trifluoromethyl diketone, affording 88% yield and 70% ee of the fluorinated hydroxylketone product.

Cinchona alkaloid/TMAF combination: Enantioselective trifluoromethylation of aryl aldehydes

The catalytic enantioselective trifluoromethylation reaction of aromatic aldehydes using the Ruppert-Prakash reagent (Me3SiCF3) has been disclosed, with an operationally simple procedure, based on the combination of sterically demand

The enantioselective trifluoromethylation of aromatic aldehydes by quaternary ammonium bromide and (IPr)CuF at low catalyst loading

A general catalytic enantioselective trifluoromethylation of aromatic aldehydes using (IPr)CuF and quinidine-derived quaternary ammonium salt as catalysts has been developed. A wide range of aromatic aldehydes are converted to the corresponding products in up to 92% yield and 81% ee at 2 mol% of catalyst loading.

Asymmetric trifluoromethylation of aromatic aldehydes by cooperative catalysis with (IPr)CuF and quinidine-derived quaternary ammonium salt

A general enantioselective trifluoromethylation of aldehydes has been developed using (IPr)CuF and quinidine-derived quaternary ammonium salt as the cooperative catalyst. Thus, a wide range of aromatic aldehydes have been converted to the corresponding products in up to 92% yield and 81% ee at 2 mol% of catalyst loading. The greatly enhanced activity and enantioselectivity result from the initiative generation of active [(IPr)CuCF3] as well as additional coordination activation of other copper species.

Rational electronic tuning of CBS catalyst for highly enantioselective borane reduction of trifluoroacetophenone

α,α,α-Trifluoroacetophenone (2), which is susceptible to noncatalytic reduction by BH3, could be reduced to chiral alcohol up to 90% ee by using electronically tuned-CBS catalyst (1) with BH3. The enantioselectivities highly correlated with the differential orbital energies between 1-BH3 adduct and 2, which were calculated by DFT method.

SOLID FORMS OF (S)-2-AMINO-3-(4-(2-AMINO-6-((R)-2,2,2-TRIFLUORO-1-(3'-METHOXYBIPHENYL- 4-YL)ETHOXY)PYRIMIDIN-4-YL)PHENYL) PROPANOIC ACID AND METHODS OF THEIR USE

Solid forms of (S)-2-amino-3-(4-(2-amino-6-((R)-2,2,2-trifluoro-1-(3'-methoxybiphenyl-4-yl)ethoxy)pyrimidin-4-yl)phenyl)propanoic acid and salts thereof are disclosed

Synthesis of novel C2-symmetric chiral crown ethers and their application to enantioselective trifluoromethylation of aldehydes and ketones

Synthesis of novel C2-symmetric chiral crown ethers and their application to enantioselective trifluoromethylation of aldehydes and ketones are discussed. The use of a series of C2-symmetric chiral crown ethers 2 or 3 derived from commercially available (R)-1,1′-bi-2-naphthol for the enantioselective trifluoromethylation of 2-naphthyl aldehyde 1a with (trifluoromethyl)trimethylsilane in the presence of a base was attempted. Iodo-substituted crown ether 2b was found to be the most effective in the model reaction. Moderate enantioselectivities were observed for the trifluoromethylation of both aryl or alkyl aldehydes and alkyl aryl ketones in 21-44% ees. Although the ees are still improvable, this is the first example of a chiral crown ether-catalyzed enantioselective trifluoromethylation reaction.

Nonenzymatic kinetic resolution of racemic 2,2,2-trifluoro-1-aryl ethanol via enantioselective acylation

Kinetic resolution of a series of 2,2,2-trifluoro-1-aryl ethanol with (R)-benzotetramisole as the catalyst has been investigated. The result showed that when the aryl group in the substrate was a phenyl (or a phenyl substituted by an electron-donating group) or a naphthyl (an extended phenyl) group, the system could give an s value higher than 20. Preparative KR examples demonstrated the applicability of this method in the preparation of some of enantiomerically pure 2,2,2-trifluoro-1-aryl ethanol or 2,2,2-trifluoro-1-aryl-ethyl iso-butyrate.

Platinum-catalyzed enantioselective hydrogenation of aryl-substituted trifluoroacetophenones

The hydrogenation of 2,2,2-trifluoroacetophenones with different aryl-substituents (CF3, N(Me)2 and Me) has been studied over Pt/Al2O3 modified by cinchonidine, its hydrochloride or O-methyl cinchonidine. Electr