28122-27-2

Usage

InChI:InChI=1/C15H16/c1-12-8-13(2)10-15(9-12)11-14-6-4-3-5-7-14/h3-10H,11H2,1-2H3

Upstream product

• 108-90-7 chlorobenzene 
• 108-67-8 1,3,5-trimethyl-benzene 
• 5350-41-4 trimethylbenzylammonium bromide 
• 172975-69-8 3,5-dimethylphenyl boronic acid 
• 34696-73-6 3,5-dimethyphenylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 13389-71-4 (3,5-dimethylphenyl)(phenyl)methanol 
• 10507-52-5 benzyl N,N-dimethylcarbamate 
• 1024-41-5 benzyl tosylate 
• 100-39-0 benzyl bromide 
• 54852-64-1 ((octyloxy)methyl)benzene 
• 108-38-3 m-xylene 
• 13389-66-7 3,5-dimethyl-benzhydryl chloride 
• 51339-25-4 3,5-dimethyl-benzhydryl bromide 

Relevant academic research and scientific papers

Ni(NIXANTPHOS)-Catalyzed Mono-Arylation of Toluenes with Aryl Chlorides and Bromides

A nickel-catalyzed cross-coupling of toluene derivatives with both aryl bromides and chlorides using a NIXANTPHOS-ligated nickel(II) complex has been developed. The key factor to success is proposed to be the catalyst activation of toluene by a cation-π complex, enabling methyl arenes (pKa ≈ 43) to be deprotonated with the relatively mild base NaN(SiMe3)2. This method facilitates access to a variety of sterically and electronically diverse hetero- and nonheteroaryl-containing diarylmethanes.

Cross coupling of benzylammonium salts with boronic acids using a well-defined N-heterocyclic carbene-palladium(ii) precatalyst

N-heterocyclic carbene-palladium(ii)-catalyzed cross-coupling of benzylammonium salts with arylboronic acids for the synthesis of diarylmethane derivatives via C-N bond activation has been developed. Notably, in the presence of the easily prepared and bench-stable Pd-PEPPSI precatalyst, the Csp3-N bond activation of the benzylammonium salt even proceeded smoothly in isopropanol at room temperature.

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.).

N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of benzyl carbamates with arylboronic acids

The Suzuki-Miyaura coupling of benzyl carbamates with arylboronic acids was achieved in an environmentally benign medium. Using water as the sole solvent, such transformation took place very well to give the desired diarylmethane derivatives in good to almost quantitative yields in the presence of a well-defined NHC-Pd(ii)-Im complex under mild conditions. It is worth noting here that this is the first example of benzyl carbamates used in coupling reaction, thus affording a new method for the formation of diarylmethanes by palladium-catalyzed C-O bond activation.

N-heterocyclic carbene-palladium(II)-1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of benzyl sulfonates with arylboronic acids

The first example of palladium-catalyzed Suzuki-Miyaura coupling between benzyl sulfonates and arylboronic acids was reported in this paper. In the presence of a well-defined, air-stable and easily available NHC-Pd(ii)-Im complex, all reactions worked well to give the desired products in good to almost quantitative yields under the optimal conditions. Electron-rich, -neutral, -poor and sterically-hindered substituents on both substrates are tolerated in such transformation, providing a convenient, efficient and alternative method for the synthesis of diarylmethanes.

Benzylation of arenes with benzyl ethers promoted by the in situ prepared superacid BF3-H2O

An efficient and environmentally friendly benzylation of arenes with benzyl ethers as benzyl donors using BF3-Et2O to generate in situ the superacid BF3-H2O as an efficient promotor has been described. A wide variety of functional groups have been investigated and found to be compatible to give the desired diarylmethanes in yields of up to 99%. The crucial role of the moisture content in this transformation has been demonstrated by detailed investigations. This journal is the Partner Organisations 2014.

Kinetics of the solvolyses of benzhydryl derivatives: Basis for the construction of a comprehensive nucleofugality scale

A series of 21 benzhydrylium ions (diarylmethylium ions) are proposed as reference electrofuges for the development of a general nucleofugality scale, where nucleofugality refers to a combination of leaving group and solvent. A total of 167 solvolysis rate constants of benzhydrylium tosylates, bromides, chlorides, trifluoroacetates, 3,5-dinitrobenzoates, and 4-nitroben-zoates, two-thirds of which have been determined during this work, were subjected to a least-squares fit according to the correlation equation log k 25°C = Sf(Nf + Ef), where s f and Nf are nucleofuge-specific parameters and E f is an electrofuge-specific parameter. Although nucleofuges and electrofuges characterized in this way cover more than 12 orders of magnitude, a single set of the parameters, namely sf, Nf, and E f, is sufficient to calculate the solvolysis rate constants at 25°C with an accuracy of ± 16%. Because sf ≈ 1 for all nucleofuges, that is, leaving group/ solvent combinations, studied so far, qualitative discussions of nucleofugality can be based on Nf.

Diamino compounds and methods for preparing them

An object of the invention is to propose diamino compounds expressed by the following general formula (1) which are suitable to obtain a raw material, a polyimide resin, for a liquid crystal aligning film without any image sticking and with a high voltage holding ratio at from a low temperature to a high temperature as well as the preparation thereof: STR1

Synthesis of diaryl methanes by Friedel-Craft condensation of benzalazines with aromatic hydrocarbons

The Friedel-Craft condensation between benzalazines and aromatic hydrocarbons provide a convenient method for the preparation of unsymmetrical diaryl methanes.

PREPARATION OF SOME TRIMETHYL- AND METHYLETHYLBIPHENYLS AND REACTIVITY OF AROMATIC HYDROCARBONS IN THE GOMBERG REACTION

Trimethyl- and methylethylbiphenyls with the alkyl groups in the both phenyl rings have been prepared by the Gomberg reaction and identified by the capillary gas-liquid chromatography.Depending on choice of the aromatic hydrocarbon either individual isomers or their mixtures (three at the most) have been obtained which were contaminated with compounds of diarylmethane type in many cases.The methylethylbiphenyls have only been prepared as mixtures contaminated with diarylmethanes.These side products have been prepared by independent syntheses.A method has been developed for isolation and separation of mixtures of trimethyl- and methylethylbiphenyls from the reaction products containing tarry products.The method is suitable for preparation of small amounts of some analytical standards.The HMO method has been used for calculation of values of the radical superdelocalizabilities at individual centres in the molecules of o-, m- and p-xylene, toluene and ethylbenzene, and these values have been compared with composition of the Gomberg reaction products from these hydrocarbons.The competitive technique has been used for comparison of the reactivities of the mentioned aromatic substrates in the Gomberg reactions.