13540-56-2

Usage

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

Upstream product

• 95-64-7 4-amino-o-xylene 
• 108-88-3 toluene 
• 87-59-2 2,3-Dimethylaniline 
• 95-47-6 o-xylene 
• 14642-79-6 benzyloxy-trimethylsilane 
• 100-42-5 styrene 
• 55499-43-9 3,4-dimethyl phenylboronic acid 
• 100-44-7 benzyl chloride 
• 100-51-6 benzyl alcohol 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 583-71-1 4-bromo-o-xylene 
• 55791-06-5 benzyl mesylate 
• 31599-61-8 3,4-dimethyliodobenzene 

Downstream Products

• 2571-39-3 (3,4-dimethylphenyl)(phenyl)methanone 
• 106147-73-3 4-[2-(3,4-Dimethyl-phenyl)-2-phenyl-ethyl]-1H-imidazole 

Relevant academic research and scientific papers

Functional mesoporous poly (ionic liquid) derived from P123: From synthesis to catalysis and alkylation of styrene and o-xylene

A novel strategy was proposed for the fabrication of high-performance acidic mesoporous poly ionic liquids catalyst. In this work, mesoporous poly ionic liquids (MPILs) were synthesized with P123 (PEO20PPO70PEO20) served a

Transition-Metal-Free Suzuki-Type Cross-Coupling Reaction of Benzyl Halides and Boronic Acids via 1,2-Metalate Shift

Cross-coupling of organoboron compounds with electrophiles (Suzuki-Miyaura reaction) has greatly advanced C-C bond formation and has been well received in medicinal chemistry. During the past 50 years, transition metals have played a central role throughout the catalytic cycle of this important transformation. In this process, chemoselectivity among multiple carbon-halogen bonds is a common challenge. In particular, selective oxidative addition of transition metals to alkyl halides rather than aryl halides is difficult due to unfavorable transition states and bond strengths. We describe a new approach that uses a single organic sulfide catalyst to activate both C(sp3) halides and arylboronic acids via a zwitterionic boron "ate" intermediate. This "ate" species undergoes a 1,2-metalate shift to afford Suzuki coupling products using benzyl chlorides and arylboronic acids. Various diaryl methane analogues can be prepared, including those with complex and biologically active motifs. The reactions proceed under transition-metal-free conditions, and C(sp2) halides, including aryl bromides and iodides, are unaffected. The orthogonal chemoselectivity is demonstrated in the streamlined synthesis of highly functionalized diaryl methane scaffolds using multi-halogenated substrates. Preliminary mechanistic experiments suggest both the sulfonium salt and the sulfur ylide are involved in the reaction, with the formation of sulfonium salt being the slowest step in the overall catalytic cycle.

MoO3 supported on ordered mesoporous zirconium oxophosphate: An efficient and reusability solid acid catalyst for alkylation and esterification

A series of molybdenum oxide supported on ordered mesoporous zirconium oxophosphate (MoO3/M-ZrPO) materials with different MoO3 loadings (0–20 wt%) and calcination temperatures (500–900 °C) have been designed, synthesized and employed as solid acid catalysts in alkylation and esterification. The XRD, TG-DSC, H2-TPR, N2-physisorption and TEM characterizations were taken to investigate the structural properties and states of introduced MoO3 species. The influence of MoO3 loadings and calcination temperatures in catalytic performance was detailedly investigated and optimal catalytic activity was reached at 10 wt% MoO3 loadings and treated at 700 °C. Moreover, MoO3/M-ZrPO catalysts exhibited outstanding catalytic performance in Friedel-Crafts alkylation of different aromatic compounds and esterification of levulinic acid with 1-butanol. Furthermore, it was noteworthy that the catalyst had superior reusability and no noticeable declines were observed in catalytic performance even after seven runs.

Benzylation with Benzyl Alcohol Catalyzed By [ChCl][TfOH]2, a Br?nsted Acidic DES with Reaction Control Self-Separation Performance

Abstract: A deep eutectic solvent with strong Br?nsted acidity was prepared easily by choline chloride and trifluoromethanesulfonic acid. The obtained [ChCl][TfOH]2 catalyst which was characterized by FT-IR, 1H NMR and TG, possessed greatly enhanced stability than trifluoromethanesulfonic acid, and exhibited excellent catalytic performance in benzylation with benzyl alcohol. Especially, the prepared [ChCl][TfOH]2 catalyst could dissolve into the reactants to realize homogeneous catalysis, and then self-separate from the organic phase after reaction due to the entire consumption of benzyl alcohol. As a result, the catalyst could be recovered and reused simply for six-runs without noticeable loss of catalytic performance. Graphical Abstract: [Figure not available: see fulltext.].

Bisulfate Salt-Catalyzed Friedel-Crafts Benzylation of Arenes with Benzylic Alcohols

We report here a method of direct Friedel-Crafts benzylation of arenes with benzylic alcohols using cheap and readily available bisulfate salt as the catalyst in hexafluoroisopropanol. The catalytic system is powerful with a quite diverse group of functionalized arenes and benzylic alcohols. These mild conditions provide a straightforward synthesis of a variety of unsymmetrical diarylmethanes in high yield with good to high regioselectivity. An SN1 mechanism involving activation of the hydroxy group through a hydrogen bond is proposed.

T-BuONa-Mediated Transition-Metal-Free Autoxidation of Diarylmethanes to Ketones

Autoxidative sp3 C-H transformation of diarylmethanes has been demonstrated using O2-mediation by t-BuONa. This protocol enables an alternative route for the access to diaryl ketones from benzyl derivatives in good to excellent yields under mild reaction conditions, without transition metal catalysts or additional chemical oxidants.

Synthesis of Di- and Triarylmethanes through Palladium-Catalyzed Reductive Coupling of N -Tosylhydrazones and Aryl Bromides

A palladium-catalyzed reductive coupling between N-tosylhydrazones and aryl bromides has been developed. The reaction provides an efficient method for the synthesis of diarylmethanes and triarylmethanes via the formation of C(sp2)-C(sp3) single bonds. This new methodology for the synthesis of diarylmethanes and triarylmethanes is featured by the ready availability of the starting materials, mild reaction conditions, and the tolerance of wide range of functional groups. The reaction follows a pathway including palladium carbene formation, migratory insertion, and reduction of the alkylpalladium(II) intermediate.

Alternative approach toward the generation of benzylic zinc reagent: Direct oxidative addition of active zinc into the carbon-oxygen bond of benzyl mesylates

The use of highly active zinc, prepared by the Rieke method, for the direct preparation of benzylic zinc mesylate was investigated. The oxidative addition of highly active zinc to benzyl mesylate was easily completed under mild conditions. The resulting benzylic zinc mesylates were employed in subsequent cross-coupling reactions with a broad range of electrophiles, and the formation of the corresponding products was successful.

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.

Iron-containing defect-rich mixed metal oxides for Friedel-Crafts alkylation

Several stable iron-containing spinel oxides with the composition CuFe 2O4 or FeCr2O4 were prepared by different methods including thermal nitrate decomposition, combustion synthesis, and mechano-chemical synthesis. Materials were compared to commercially available spinels produced by conventional ceramic route with respect to their structural properties and catalytic activity. Phase compositions and microstructures of the catalysts were studied in detail. The catalysts were tested in the Friedel-Crafts alkylation of various aromatic compounds with different alkyl halides as alkylating agents. Microstructural properties (microstrains) of the synthesized binary oxides have been identified as a reason for the increased reactivity. Even at low reaction temperatures of 50-70 °C catalysts maintained their high activity resulting in TOFs of up to 3000 h -1 and excellent selectivity with total heterogeneous behavior in catalysis.