33757-36-7

Upstream product

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 34328-30-8 4-trifluoromethyl-4′-methylbenzophenone 
• 19226-36-9 3-phenyl-5H-1,4,2-dioxazol-5-one 
• 402-51-7 4-(trifluoromethyl)phenylmagnesium bromide 
• 104-87-0 4-methyl-benzaldehyde 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 455-13-0 4-Iodobenzotrifluoride 
• 455-18-5 4-CF₃C₆H₄CN 
• 4463-41-6 2-(p-tolyl)-1,3,2-dioxaborinane 

Downstream Products

• 87901-58-4 C₁₅H₁₂F₃⁽¹⁺⁾ 
• 32045-08-2 Dimethyl-{2-[p-tolyl-(4-trifluoromethyl-phenyl)-methoxy]-ethyl}-amine 
• 34328-30-8 4-trifluoromethyl-4′-methylbenzophenone 
• 170789-13-6 1-methyl-4-(4-(trifluoromethyl)benzyl)benzene 

Relevant academic research and scientific papers

Nickel Catalyzed Intermolecular Carbonyl Addition of Aryl Halide

In this study, we develop a nickel-catalyzed carbonyl arylation reaction employing aldehydes with aryl and allyl halides. Various aryl, α,β-unsaturated aldehyde and aliphatic aldehydes can be converted into their corresponding secondary alcohols in moderate-to-high yields. In addition, we extended this approach to develop an asymmetric reductive coupling reaction that combines nickel salts with chiral bisoxazoline ligands to give secondary alcohols with moderate enantioselectivity.

An Efficient Ga(OTf)3/Isopropanol Catalytic System for Direct Reduction of Benzylic Alcohols

This study aims to report the first gallium-catalyzed direct reduction of benzylic alcohols using isopropanol as a reductant. The reaction proceeds via gallium catalyst-assisted hydride transfer of the in situ-generated benzylic isopropyl ether. The method generates only water and acetone as byproducts and thus provides an atom-economic and environmentally friendly approach to the synthesis of di- and triarylmethanes, which are important substructures in various bioactive compounds and functional materials. (Figure presented.).

Co(III)-Catalyzed Synthesis of Quinazolines via C-H Activation of N-Sulfinylimines and Benzimidates

C-H activation of arenes has been established as an important strategy for heterocycle synthesis via annulations between arenes and unsaturated coupling partners. However, nitriles failed to act as such a coupling partner. Dioxazolones have been employed as a synthon of nitriles, and subsequent coupling with arenes such as N-sulfinylimines and benzimidates bearing a functionalizable directing group provided facile access to two classes of quinazolines under Co(III)-catalysis.

Continuous preparation of arylmagnesium reagents in flow with inline IR monitoring

A newly developed microscale ReactIR flow cell was used as a convenient and versatile inline analytical tool for Grignard formation in continuous flow chemical processing. The LiCl-mediated halogen/Mg exchange reaction was used for the preparation of functionalized arylmagnesium compounds from aryl iodides or bromides. Furthermore, inline IR monitoring was used for the analysis of conversion and possible byproduct formation, as well as a potential tool for elucidation of mechanistic details. The results described herein indicate that the continuous flow systems are effective for highly exothermic reactions such as the Grignard exchange reaction due to fast mixing and efficient heat transfer.

Alkynes as activators in the nickel-catalysed addition of organoboronates to aldehydes

Alkynes act not as substrates but as co-catalysts in the presence of a nickel catalyst, an organoboronate and an aldehyde to promote the addition reaction between the substrates in combination with H2O. The Royal Society of Chemistry 2005.

Direct observation of aldehyde insertion into rhodium-aryl and -alkoxide complexes

Several organorhodium(I) complexes of the general formula (PPh3)2(CO)RhR (R = p-tolyl, o-tolyl, Me) were isolated and were shown to insert aryl aldehydes into the aryl-rhodium(I) bond. Under nonaqueous conditions, these reactions provided ketones in good yield. The stability of the arylrhodium(I) complexes allowed these reactions to be run also in mixtures of THF and water. In this solvent system, diarylmethanols were generated exclusively. Mechanistic studies support the formation of ketone and diarylmethanol by insertion of aldehyde into the rhodium-aryl bond and subsequent β-hydride elimination or hydrolysis to form diaryl ketone or diarylmethanol products. Kinetic isotope effects and the formation of diarylmethanols in THF/water mixtures are inconsistent with oxidative addition of the acyl carbon-hydrogen bond and reductive elimination to form ketone. Moreover, the intermediate rhodium diarylmethoxide formed from insertion of aldehyde was observed directly during the reaction. Its structure was confirmed by independent synthesis. This complex undergoes β-hydrogen elimination to form a ketone. This alkoxide also reacts with a second aldehyde to form esters by insertion and subsequent β-hydrogen elimination. Thus, reactions of arylrhodium complexes with an excess of aldehyde formed esters by a double insertion and β-hydrogen elimination sequence.

Metal-catalyzed release of supported boronic acids for C-C bond formation

matrix presented The viability of solid-supported boronic acids as reagents for Suzuki couplings and nucleophilic additions to aldehydes and enones was successfully demonstrated. This metal-catalyzed cleavage strategy allows the synthesis of a series of functionalized biphenyl products, benzylic alcohols, and β-substituted ketones.