350830-26-1

Upstream product

• 623-26-7 terephthalonitrile 
• 95-47-6 o-xylene 
• 623-00-7 4-bromobenzenecarbonitrile 
• 16419-60-6 2-Methylphenylboronic acid 
• 126747-14-6 4-cyanophenylboronic acid 
• 874-86-2 4-cyanobenzyl chloride 
• 1632070-88-2 potassium trifluoro(2-methylbenzyl)borate 
• 1352919-01-7 N-((4-cyanobenzyl)oxy)-N-methylacetamide 
• 108-88-3 toluene 

Relevant academic research and scientific papers

Cucurbit[7]uril promoting PdCl2-catalyzed cross-coupling reaction of benzyl halides and arylboronic acids in aqueous media

The research provides a novel approach for producing diarylmethane derivatives using CB[7]-NaCl-PdCl2catalyzed Suzuki cross-coupling reaction of benzyl chloride derivatives and arylboronic acids in ethanol aqueous solution.

The Dual Role of Benzophenone in Visible-Light/Nickel Photoredox-Catalyzed C?H Arylations: Hydrogen-Atom Transfer and Energy Transfer

A dual catalytic protocol for the direct arylation of non-activated C(sp3)?H bonds has been developed. Upon photochemical excitation, the excited triplet state of a diaryl ketone photosensitizer abstracts a hydrogen atom from an aliphatic C?H bond. This inherent reactivity was exploited for the generation of benzylic radicals which subsequently enter a nickel catalytic cycle, accomplishing the benzylic arylation.

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 Suzuki cross-coupling of benzyltrimethylammonium salts via C-N bond cleavage

A palladium catalyzed Suzuki cross-coupling for construction of Csp3-Csp2 bond via Csp3-N bond activation of benzyltrimethyl-ammonium salt is described. This reaction not only offered a highly efficient approach to diarylmethanes but also paved the way for the application of benzyltrimethylammonium salts in the palladium catalyzed cross coupling reactions.

Visible-Light-Mediated Aromatic Substitution Reactions of Cyanoarenes with 4-Alkyl-1,4-dihydropyridines through Double Carbon-Carbon Bond Cleavage

Novel aromatic substitution reactions of cyanoarenes with 4-alkyl-1,4-dihydropyridines as alkylating reagents in the presence of a catalytic amount of a photoredox catalyst proceed smoothly to give the corresponding alkyl-substituted arenes in good to high yields. The present reaction system realizes a novel C-C bond-forming reaction between two fragments generated from the C-C bond-cleavage reactions of two independent substrates.

Efficient synthesis of diarylmethane derivatives by PdCl2 catalyzed cross-coupling reactions of benzyl chlorides with aryl boronic acids in aqueous medium

The research provides a simple and efficient method for preparing diarylmethane derivatives using the cross-coupling reaction of benzyl chlorides and aryl boronic acids catalyzed by palladium chloride in DMF aqueous solution without additional ligand.

Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis

The routine application of Csp3-hybridized nucleophiles in cross-coupling reactions remains an unsolved challenge in organic chemistry. The sluggish transmetalation rates observed for the preferred organoboron reagents in such transformations are a consequence of the two-electron mechanism underlying the standard catalytic approach. We describe a mechanistically distinct single-electron transfer-based strategy for the activation of organoboron reagents toward transmetalation that exhibits complementary reactivity patterns. Application of an iridium photoredox catalyst in tandem with a nickel catalyst effects the cross-coupling of potassium alkoxyalkyl- and benzyltrifluoroborates with an array of aryl bromides under exceptionally mild conditions (visible light, ambient temperature, no strong base). The transformation has been extended to the asymmetric and stereoconvergent cross-coupling of a secondary benzyltrifluoroborate.

Friedel-crafts benzylation of activated and deactivated arenes

NO going back makes possible facile Friedel-Crafts benzylations with moderate reaction temperatures, simple reaction workups, and improved substrate scope for the formation of synthetically important diarylmethanes (see scheme). Upon complexation with BF3?OEt2, hydroxamates serve as reversible leaving groups that stabilize highly reactive carbocations. Even deactivated arenes and electron-deficient benzylhydroxamates react cleanly under these conditions.