52126-09-7

Upstream product

• 5720-07-0 4-methoxyphenylboronic acid 
• 17201-43-3 4-cyanobenzyl bromide 
• 623-00-7 4-bromobenzenecarbonitrile 
• 40156-88-5 p-methoxybenzyl diethyl phosphate 
• 874-86-2 4-cyanobenzyl chloride 
• 824-94-2 p-methoxybenzyl chloride 
• 312693-17-7 (4-methoxybenzyl)zinc(II) chloride 
• 174813-84-4 4-(hydroxy(4-methoxyphenyl)methyl)benzonitrile 
• 412044-48-5 (4-cyanophenyl)magnesium bromide 
• 123-11-5 4-methoxy-benzaldehyde 
• 3058-39-7 4-iodobenzonitrile 
• 15586-16-0 4-methoxybenzyloxycarbonyl chloride 
• 623-26-7 terephthalonitrile 
• 1416982-07-4 1-(4-methoxyphenyl)-N,N,N-trimethylmethanaminium trifluoromethanesulfonate 

Relevant academic research and scientific papers

Palladium-catalyzed cross-coupling of benzyltitanium(IV) reagents with aryl fluorides

The first palladium-catalyzed cross-coupling between benzyltitanium(IV) reagents with aryl fluorides is reported. A variety of diarylmethanes can be prepared in good to excellent yields by the catalyst system of PdCl2(dppf)2 associated with 1-[2-(di-tert-butylphosphanyl)phenyl]-4-methoxypiperidine. This reaction offered a highly efficient approach to diarylmethanes that are commonly found in life-changing drug molecules. Graphical abstract: [Figure not available: see fulltext.]

Method for synthesizing diaryl methane derivative

The invention aims to provide a method for synthesizing a diaryl methane derivative. The method is characterized in that tris (dibenzylideneacetone) dipalladium is used as a catalyst, an organic antimony compound is used as a nucleophilic reagent, benzyl bromide and benzyl chloride are used as electrophilic reagents, toluene is used as a solvent, and the diaryl methane derivative is synthesized through direct cross coupling under the air atmosphere condition. The method has the characteristics of good substrate universality, good functional group tolerance, simplicity and convenience in operation and the like.

Nickel catalysis enables convergent paired electrolysis for direct arylation of benzylic C-H bonds

Convergent paired electrosynthesis is an energy-efficient approach in organic synthesis; however, it is limited by the difficulty to match the innate redox properties of reaction partners. Here we use nickel catalysis to cross-couple the two intermediates

Nickel catalyzed deoxygenative cross-coupling of benzyl alcohols with aryl-bromides

A nickel-catalyzed cross-electrophile coupling of benzyl alcohols with aromatic bromides has been developed. This deoxygenative cross-coupling occurs under mild reaction conditions at ambient temperature affording diarylmethanes, or 1,3-diarylpropenes from benzyl allyl alcohols. The system demonstrated good chemoselectivity tolerating an assortment of reactive functional groups.

N-heterocyclic carbene–palladium complexes for Suzuki–Miyaura coupling reaction with benzyl chloride and aromatic boronic acid leading to diarylmethanes

A family of N-heterocyclic carbene–palladium(II)–N,N-dimethylbenzylamine complexes ((NHC)LPdCl2; L?=?N,N-dimethylbenzylamine) were synthesized as well as characterized using single-crystal X-ray diffraction and spectroscopic data. These complexes exhibited higher catalytic activities for the Suzuki reaction of benzyl chlorides to afford diarylmethanes under milder conditions than other efficient (NHC)LPdCl2 complexes. Using the optimum conditions, the expected coupling products were obtained in moderate to high yields. All reactions were carried out in air and all starting materials were used as supplied without purification.

Palladium-Catalyzed Hiyama Coupling of Benzylic Ammonium Salts via C-N Bond Cleavage

The first palladium-catalyzed Hiyama cross-coupling of arylsilanes with benzyltrimethylammonium salts is reported. The reaction proceeds smoothly to facilitate C(sp2)-C(sp3) bond formation via cleavage of the C-N bond and provides a useful approach to various diarylmethanes with a broad substrate scope and excellent functional group tolerance in good to excellent yields.

Visible-light-mediated external-reductant-free reductive cross coupling of benzylammonium salts with (hetero)aryl nitriles

Herein we report a novel visible-light-mediated external reductant-free reductive cross coupling for the construction of C sp2–C sp3 bonds. A variety of benzylammonium salts underwent selective coupling with (hetero)aryl nitriles to

Diarylmethane compounds as well as preparation method and application thereof

The invention discloses diarylmethane compounds as well as a preparation method and application thereof. The diarylmethane compounds have a molecular structural general formula as defined by a generalformula (I) in the description. The preparation method of the diarylmethane compounds comprises the steps of adding a benzyl halogenated hydrocarbon compound A and an arylboronic acid B into a reaction system containing an organic small-molecular catalyst, an alkali reagent and a solvent, and performing a reaction to prepare the compounds. The diarylmethane compounds provided by the invention contain electron withdrawing groups and an electron-donating group substituted diarylmethane basic structure, and can be widely used for synthesis of pharmaceutical intermediates, particularly polysubstituted methane compounds, and preparation of functional materials; and the preparation method has a simple process and low requirements for reaction conditions, the reaction process is safe and controllable, the atomic utilization rate and production efficiency are high, the regioselectivity and stereoselectivity of the products are efficiently ensured, a frontier science small-molecule organocatalysis concept is introduced, and the method is friendly to the environment.

Deoxygenative cross-electrophile coupling of benzyl chloroformates with aryl iodides

This work describes Ni-catalyzed cross-electrophile coupling of benzyl chloroformate derivatives with aryl iodides that generates a wide range of diaryl methane products. The mild reaction conditions merit the C-O bond radical fragmentation of benzyl chloroformates via halide abstraction or a single electron reduction by a Ni catalyst. This work offers a new substrate type for cross-electrophile couplings.

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.