53756-61-9

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-phenyl-(4-trifluoromethyl-phenyl)-methanol is used as a building block for the synthesis of various pharmaceuticals due to its unique structural features and reactivity. Its trifluoromethyl group enhances the compound's properties, making it a valuable intermediate in the development of new drugs.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (S)-phenyl-(4-trifluoromethyl-phenyl)-methanol is used as a synthetic intermediate for designing and developing novel compounds with potential therapeutic applications. Its structural diversity and the presence of the trifluoromethyl group contribute to its utility in creating innovative molecules with improved pharmacological properties.
Used in Organic Chemistry:
(S)-phenyl-(4-trifluoromethyl-phenyl)-methanol is also utilized in organic chemistry as a synthetic intermediate for the preparation of various organic compounds. Its reactivity and structural characteristics make it a versatile building block for creating a wide range of molecules with different applications in various industries.
Used in Chemical Research:
In the realm of chemical research, (S)-phenyl-(4-trifluoromethyl-phenyl)-methanol serves as a valuable compound for studying the effects of the trifluoromethyl group on the properties and reactivity of organic molecules. This research can lead to a better understanding of the role of trifluoromethyl groups in chemical reactions and the development of new synthetic strategies and methodologies.

Upstream product

• 728-86-9 phenyl[4-(trifluoromethyl)phenyl]methanone 
• 3262-89-3 triphenylboroxine 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 98-80-6 phenylboronic acid 
• 100-58-3 phenylmagnesium bromide 
• 108-86-1 bromobenzene 
• 841-76-9 triphenylaluminium 
• 395-23-3 phenyl(4-(trifluoromethyl)phenyl)methanol 
• 97-72-3 2-Methylpropionic anhydride 
• 591-51-5 phenyllithium 
• 100-52-7 benzaldehyde 
• 16635-23-7 phenyltriisopropoxytitanium(IV) 
• 1078-58-6 diphenylzinc 
• 128796-39-4 4-trifluoromethylphenylboronic acid 

Downstream Products

• 1375744-31-2 C₁₅H₁₃F₃ 
• 1375744-48-1 C₁₇H₁₇F₃O₂ 

Relevant academic research and scientific papers

Bio-inspired asymmetric aldehyde arylations catalyzed by rhodium-cyclodextrin self-inclusion complexes

Transition-metal catalysts are powerful tools for carbon-carbon bond-forming reactions that are difficult to achieve using native enzymes. Enzymes that exhibit inherent selectivities and reactivities through host-guest interactions have inspired widesprea

Isosterically designed chiral catalysts: Rationale, optimization and their application in enantioselective nucleophilic addition to aldehydes

Proline-based N,N′-dioxide ligands were designed on the basis of isosteric approach, and were successfully applied in enantioselective nucleophilic addition to aldehydes. In the presence of 10 mol% of chiral ligand 1b, enantioselective addition of diethylzinc to aldehydes provided the corresponding secondary alcohols in up to 90% isolated yield and up to 99% ee. Similarly, using 3e as chiral ligand, enantioselective arylation and alkynylation of aldehydes also proceeded readily, leading to the desired chiral alcohols in up to 92% isolated yield at 99% ee and 80% isolated yields and up to 84% ee, respectively. The current work would shed light on expanding the structure diversity in the design of chiral ligands and chiral catalysts.

Enantioselective Diarylcarbene Insertion into Si-H Bonds Induced by Electronic Properties of the Carbenes

Catalytic enantioselection usually depends on differences in steric interactions between prochiral substrates and a chiral catalyst. We have discovered a carbene Si-H insertion in which the enantioselectivity depends primarily on the electronic characteristics of the carbene substrate, and the log(er) values are linearly related to Hammett parameters. A new class of chiral tetraphosphate dirhodium catalysts was developed; it shows excellent activity and enantioselectivity for the insertion of diarylcarbenes into the Si-H bond of silanes. Computational and mechanistic studies show how the electronic differences between the two aryls of the carbene lead to differences in energies of the diastereomeric transition states. This study provides a new strategy for asymmetric catalysis exploiting the electronic properties of the substrates.

Asymmetric Hydrophosphination of Heterobicyclic Alkenes: Facile Access to Phosphine Ligands for Asymmetric Catalysis

Asymmetric hydrophosphination is the most atomically economical and straightforward approach to the construction of chiral organophosphorus compounds. Good stereoselectivities have been achieved in asymmetric hydrophosphination of an electron-deficient C=

Enantiopure Methyl- A nd Phenyllithium: Mixed (Carb-)Anionic Anisyl Fencholate-Aggregates

Methyl- A nd phenyllithium aggregates with enantiopure anisyl fencholate units form after reaction of organolithium reagent with (+)-anisyl fenchol in hydrocarbon and some ethereal solvents. These carbanionic aggregates are characterized by X-ray crystal analyses and exhibit both 3:1 stoichiometry and distorted cubic Li4O3C1 cores, in which three lithium ions coordinate the carbanion (i.e., methylide or phenylide). These three lithium ions define a Lewis acidic surface (Li3), binding the carbanion and expanding with the steric demand of the carbanion (i.e., from Me: 2.62 ?2, over n-Bu: 2.65 ?2 (previous work) to Ph: 2.79 ?2). Methylation and phenylation reactions of various prochiral aldehydes employing these methyllithium and phenyllithium aggregates yield alcohols with up to 44% ee. To rationalize the formation of the mixed (carb-)anionic aggregates, aggregate formation energies, describing co-condensations of RLi (R = Me, Ph, n-Bu) and lithium fencholates, are computed for the 3:1 and 2:2 stoichiometries. These computed aggregate formation energies point to preferences for 3:1 over 2:2 aggregates, as it is also apparent from experimental aggregate formations, confirmed by X-ray crystal analyses. In close analogy to the X-ray crystal structures, the computed Li3 surfaces increase with increasing steric demand of the carbanions. The chiral, mixed (carb-)anionic RLi-fencholate aggregates hence adapt to different carbanion sized and arise not only with small (Me) or primary carbanions (n-Bu) but even with the larger secondary phenyl anion.

Highly enantioselective asymmetric reactions involving zinc ions promoted by chiral aziridine alcohols

Enantiomerically pure, chiral secondary and tertiary aziridine alcohols (including the aziridine analogue of ProPhenol—AziPhenol) have proven to be highly effective catalysts for enantioselective asymmetric reactions in the presence of zinc ions, including arylation of aromatic aldehydes, epoxidation of chalcone and addition of diethylzinc to aldehydes, leading to the desired chiral products in high chemical yields (up to 90%) and with ee's up to 90%. A higher catalytic activity of Prophenol-type bis(aziridine alcohol) in the aforementioned asymmetric transformations has been demonstrated.

Chiral thiophosphoramide catalyzed asymmetric aryl transfer reactions for the synthesis of functional diarylmethanols

In this investigation, chiral thiophosphoramide 3d was easily prepared from chiral (1R,2R)-1,2-diphenylethylenediamine and then applied as an efficient chiral ligand in the catalytic asymmetric arylation reactions of various aromatic aldehydes. The corresponding diarylmethanol products were produced with good to excellent yields (up to 98%) and enantioselectivities (up to 94%). The recovery of chiral ligand 3d could be as high as 96%.

The inexpensive additive N-methylmorpholine effectively decreases the equivalents of nucleophiles in the catalytic highly enantioselective arylation of aryl aldehydes

Highly enantioselective arylation of aryl aldehydes catalyzed by (S)-H8-BINOL-Ti(Oi-Pr)2 complex in the presence of N-methylmorpholine (NMM) as an effective and inexpensive additive is described for the first time. We found high enan

Synthesis of new benzimidazolium salts and their application in the asymmetric arylation of aldehydes

A series of novel chiral benzimidazolium salts, the precursor of N-heterocyclic carbene ligands, were designed and synthesized from 1,2-dibromobenzene. In situ prepared corresponding carbenes were tested in asymmetric Rh-catalyzed arylation of aromatic aldehydes, affording chiral diarylmethanols with high yields and moderate enantioselectivities.

Kinetic resolution of secondary carbinols by a chiral N,N-4-dimethylaminopyridine derivative containing a 1,1′-binaphthyl unit: Hydrogen bonding affects catalytic activity and enantioselectivity

We developed an acylative kinetic resolution of secondary carbinols using a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1d with tert-Alcohol substituents. The reaction proceeded with a wide range of carbinols with moderate to high selectivity (s) (up to s = 79.5). Kinetic studies revealed that catalyst 1d was more catalytically active than the corresponding bis-methyl ether 1d′ or DMAP. Hydrogen bonding between tert-Alcohols of the catalyst and secondary carbinols was responsible for the enhanced reaction rate and high enantioselectivity.