89751-95-1

Upstream product

• 349-95-1 4-(trifluoromethyl)benzylic alcohol 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 1204177-13-8 4-(trifluoromethyl)benzyl 2-(4-cyanobenzylideneamino)-2,2-diphenylacetate 
• 3375-31-3 palladium diacetate 
• 127-09-3 sodium acetate 
• 104-88-1 4-chlorobenzaldehyde 
• 402-49-3 4-bromomethyltrifluoromethylbenzene 
• 127-19-5 N,N-dimethyl acetamide 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 64-19-7 acetic acid 

Downstream Products

• 34239-04-8 1-benzyl-4-(trifluoromethyl)benzene 
• 114872-59-2 diethyl 2-acetamido-2-<<4-(trifluoromethyl)phenyl>methyl>malonate 
• 1006037-09-7 2,5-dimethyl-3-[4-(trifluoromethyl)benzyl]thiophene 
• 1078758-79-8 1-(4-trifluoromethyl-benzyl)-naphthalene 
• 349-95-1 4-(trifluoromethyl)benzylic alcohol 

Relevant academic research and scientific papers

Syngas Instead of Hydrogen Gas as a Reducing Agent─A Strategy To Improve the Selectivity and Efficiency of Organometallic Catalysts

Catalytic reduction reactions play a major role in modern chemistry and are often based on hydrogen gas as a reducing agent. However, the high reactivity of hydrogen is often accompanied by low selectivity on the simple catalysts. Herein, we showed that the usage of syngas as a reducing agent can be a more efficient and selective strategy. Based on control experiments, a plausible mechanism was proposed to explain the superior performance of syngas. The versatility of this approach was demonstrated by successful application to three reactions using different metal catalysts: direct reductive amination, reductive esterification, and the tandem CH-reductive alkylation-hydrolysis-decarboxylation. Catalyst turnover numbers up to 30,000 were achieved. Moreover, the developed strategy showed improved selectivity and functional group compatibility as compared to the use of hydrogen gas.

Esterification of Tertiary Amides by Alcohols Through C?N Bond Cleavage over CeO2

CeO2 has been found to promote ester forming alcoholysis reactions of tertiary amides. The present catalytic system is operationally simple, recyclable, and it does not require additives. The esterification process displays a wide substrate scope (>45 examples; up to 93 % isolated yield). Results of a density functional theory (DFT) study combined with in situ FT-IR observations indicate that the process proceeds through rate limiting addition of a CeO2 lattice oxygen to the carbonyl group of the adsorbed acetamide species with energy barrier of 17.0 kcal/mol. This value matches well with experimental value (17.9 kcal/mol) obtained from analysis of the Arrhenius plot. Further studies by in situ FT-IR and temperature programmed desorption using probe molecules demonstrate that both acidic and basic properties are important, and consequently, CeO2 showed the best performance for the C?N bond cleavage reaction.

An approach to heterodiarylmethanes via sp2-sp3 Suzuki-Miyaura cross-coupling

The synthesis of a range of structurally diverse diarylmethanes via the Suzuki-Miyaura cross-coupling of aryl methane acetates and arylboronic acids is reported, including several challenging examples containing nitrogen, oxygen and sulfur heteroatoms in one or both coupling partners. A single set of optimized conditions was used to generate the diarylmethanes in 52-91% yield.

Electrogenerated N-heterocyclic carbene in ionic liquid: An insight into the mechanism of the oxidative esterification of aromatic aldehydes

An N-heterocyclic carbene (NHC), generated by cathodic reduction of BMIm BF4, mediates the oxidative esterification of aromatic aldehydes with organic bromides in the corresponding ionic liquid as solvent. The product recovery by simple extractive work-up with diethyl ether allowed the ionic liquid to be recycled up to 9 times for subsequent electrolyses, with no significant loss in the product yield. The isolation of an intermediate, whose structure was confirmed by synthesis and transformation into the ester, provided the key for a mechanistic insight into the reaction.

Sol-gel derived LaFeO3/SiO2 nanocomposite: Synthesis, characterization and its application as a new, green and recoverable heterogeneous catalyst for the efficient acetylation of amines, alcohols and phenols

LaFeO3/SiO2 nanocomposite was synthesized by the sol-gel process from metal nitrates and tetraethyl orthosilicate (TEOS) as the SiO2 source. The nanocomposite product was characterized by XRD, FT-IR, SEM, and surface area measurements and was used as a heterogeneous catalyst for the efficient acetylation of amines, alcohols and phenols to the corresponding acetates using acetic anhydride under solvent-free conditions. Among the various substrates, acetylation of amines was preceded rapidly, so that an amine group could be selectively acetylated in the presence of alcoholic or phenolic hydroxyl groups by the appropriate choice of reaction time. The catalyst can also be reused several times without the loss of activity. In addition, the catalytic activity of the LaFeO3/SiO2 nanocomposite was higher than that of the pure LaFeO3 nanoparticles. The method is high yielding, clean, cost effective, compatible with the substrates having other functional groups and very suitable for the practical organic synthesis.

ZnAl2O4@SiO2 nanocomposite catalyst for the acetylation of alcohols, phenols and amines with acetic anhydride under solvent-free conditions

A ZnAl2O4@SiO2 nanocomposite was prepared from metal nitrates and tetraethyl orthosilicate by the sol-gel process, and characterized by X-ray diffraction, Fourier transform infrared, transmission electron microscopy, and N2 adsorption-desorption measurements. The nanocomposite was tested as a heterogeneous catalyst for the acetylation of alcohols, phenols, and amines under solvent-free conditions. Under optimized conditions, efficient acetylation of these substrates with acetic anhydride over the ZnAl2O4@SiO2 nanocomposite was obtained. Acetylation of anilines and primary aliphatic amines proceeded rapidly at room temperature, while the reaction time was longer for the acetylation of alcohols and phenols, showing that an amine NH2 group can be selectively acetylated in the presence of alcoholic or phenolic OH groups. The catalyst can be reused without obvious loss of catalytic activity. The catalytic activity of the ZnAl2O4@SiO2 nanocomposite was higher than that of pure ZnAl2O4. The method gives high yields, and is clean, cost effective, compatible with substrates having other functional groups and it is suitable for practical organic synthesis.

H6GeMo10V2O40·16H 2O nanoparticles prepared by hydrothermal method: A new and reusable heteropoly acid catalyst for highly efficient acetylation of alcohols and phenols under solvent-free conditions

A new Keggin-type heteropoly acid, namely decamolybdodivanadogermanic acid (H6GeMo10V2O40·16H 2O), with nanosized particles (5-8 nm), has been synthesized by a hydrothermal method and characterized by elemental analysis, thermogravimetric analysis (TGA), powder X-ray diffractometry (XRD), Fourier-transform infrared spectroscopy (FTIR), UV-Visible spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM) and potentiometric titration. H6GeMo10V2O40·16H 2O revealed high catalytic activity for acetylation of various alcohols and phenols with acetic anhydride at room temperature (298 ± 2 K) and under solvent-free conditions. The catalyst can be easily recovered and used repeatedly for five cycles with a slight loss of activity. The catalytic activity of H6GeMo10V2O40· 16H2O was higher than that of other Keggin-type heteropoly acids, such as H3PW12O40, H3PMo 12O40 and H4SiW12O40.

Palladium-catalyzed decarboxylative benzylation of diphenylglycinate lmines

(Figure presented) General reaction conditions for the Pd-catalyzed decarboxylative benzylation of benzyl diphenylglycinate lmines are described. The overall procedure requires a simple catalyst/ligand combination to form a new Csp3-Csp3 bond. Microwave Irradiation greatly accelerated the transformation. Moreover, various heteroaromatlc moieties are tolerated in both the imine and ester components.

Spinel-type zinc aluminate (ZnAl2O4) nanoparticles prepared by the co-precipitation method: A novel, green and recyclable heterogeneous catalyst for the acetylation of amines, alcohols and phenols under solvent-free conditions

Zinc aluminate (ZnAl2O4) nanoparticles with an average particle size of about 8 nm were easily prepared by the co-precipitation method using aqueous ammonia solution as the precipitating agent. This nanosized spinel-type oxide was characterized by TGA, XRD, FT-IR, TEM, and surface area measurement and used as the heterogeneous catalyst for the acetylation reaction. Efficient acetylation of various amines, alcohols and phenols was carried out over ZnAl2O4 nanoparticles using acetic anhydride and/or acetyl chloride as the acetylating agents at room temperature without the use of a solvent. The method is highly selective, allowing the alcoholic hydroxyl group to be protected while the phenolic hydroxyl group remains intact, and the amine group can be acetylated in the presence of the hydroxyl group. This method is fast and has a high yield. It is also clean, safe, cost effective, compatible with substrates that have other functional groups and very suitable for practical organic synthesis. In addition, the catalyst can be reused without significant loss of activity. Indeed, the catalytic activity of the ZnAl2O4 nanoparticles is higher than that of bulk ZnAl2O4.

Cross-coupling of benzylic acetates with arylboronic acids: One-pot transformation of benzylic alcohols to diarylmethanes

Benzylic acetates reacted with arylboronic acids in the presence of a DPEphos-[Pd(η3-C3H5)Cl]2 catalyst when tert-amyl alcohol was used as a solvent, and the catalytic cross-couplings produced diarylmethanes in high yields (up to 94% isolated yield). The Royal Society of Chemistry 2005.