3678-72-6

Usage

Uses

Used in Organic Synthesis:
4-DIPHENYLMETHYLPYRIDINE is used as a ligand in organic synthesis for its ability to facilitate various chemical reactions, enhancing the efficiency and selectivity of the processes involved.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 4-DIPHENYLMETHYLPYRIDINE is utilized as an intermediate in the synthesis of various drugs, contributing to the development of new medicinal compounds.
Used in Agrochemical Production:
Similarly, in agrochemicals, 4-DIPHENYLMETHYLPYRIDINE serves as an intermediate, playing a crucial role in the creation of substances that protect crops from pests and diseases.
Used in Medicinal Applications:
4-DIPHENYLMETHYLPYRIDINE is studied for its potential as an anti-inflammatory agent, which could be beneficial in treating conditions characterized by inflammation.
4-DIPHENYLMETHYLPYRIDINE is also considered for its antioxidant properties, which may help in protecting cells from damage caused by reactive oxygen species and thus have implications in various therapeutic areas.

InChI:InChI=1/C18H15N/c1-3-7-15(8-4-1)18(16-9-5-2-6-10-16)17-11-13-19-14-12-17/h1-14,18H

Upstream product

• 626-61-9 4-Chloropyridine 
• 86-29-3 Diphenylacetonitrile 
• 1620-30-0 diphenyl(pyridin-4-yl)methanol 
• 872-85-5 pyridine-4-carbaldehyde 
• 71-43-2 benzene 
• 100-48-1 pyridine-4-carbonitrile 
• 101-81-5 Diphenylmethane 
• 117-34-0 2,2-diphenylacetic acid 
• 63591-86-6 1,3-dioxoisoindolin-2-yl 2,2-diphenylacetate 
• 776-74-9 Bromodiphenylmethane 
• 2116-65-6 4-benzyl pyridine 
• 462-06-6 fluorobenzene 
• 10034-85-2 hydrogen iodide 
• 108-90-7 chlorobenzene 

Downstream Products

• 63906-15-0 4-benzhydryl-1-(3-trimethylammonio-propyl)-pyridinium; dibromide 
• 5704-22-3 4-(diphenylmethyl)-1-methylpiperidine 
• 72964-97-7 4-benzhydryl-1-methyl-pyridinium; iodide 
• 19841-73-7 4-(Diphenylmethyl)piperidine 
• 42362-54-9 4-(chloro-diphenyl-methyl)-pyridine 
• 109975-60-2 2,2-diphenyl-2-(4-pyridyl)ethanol 
• 29958-05-2 4-(2-chloro-1,1-diphenylethyl)pyridine 
• 109975-58-8 2-(4-methylphenyl)-1,1-diphenyl-1-(4-pyridyl)ethane 
• 26344-73-0 4-(diphenylmethyl)piperidine hydrochloride 
• 1235721-19-3 Se-methyl 4-(diphenylmethylidene)-4H-azine-N-selenocarbamate 
• 1353894-18-4 trans-Na[RuCl₄(dimethylsulfoxide)(diphenyl-4-pyridylmethane)] 
• 1353894-17-3 trans-[diphenyl-4-pyridylmethane(+1H)][RuCl₄(dimethylsulfoxide)(diphenyl-4-pyridylmethane)] 
• 1522267-99-7 (diphenyl-4-pyridyl-methane)H[trans-RuCl₄(diphenyl-4-pyridyl-methane)] 
• 1620-30-0 diphenyl(pyridin-4-yl)methanol 

Relevant academic research and scientific papers

Metal-Free Heterogeneous Semiconductor for Visible-Light Photocatalytic Decarboxylation of Carboxylic Acids

A suitable protocol for the photocatalytic decarboxylation of carboxylic acids was developed with metal-free ceramic boron carbon nitrides (BCN). With visible light irradiation, BCN oxidize carboxylic acids to give carbon-centered radicals, which were trapped by hydrogen atom donors or employed in the construction of the carbon-carbon bond. In this system, both (hetero)aromatic and aliphatic acids proceed the decarboxylation smoothly, and C-H, C-D, and C-C bonds are formed in moderate to high yields (35 examples, yield up to 93%). Control experiments support a radical process, and isotopic experiments show that methanol is employed as the hydrogen atom donor. Recycle tests and gram-scale reaction elucidate the practicability of the heterogeneous ceramic BCN photoredox system. It provides an alternative to homogeneous catalysts in the valuable carbon radical intermediates formation. Moreover, the metal-free system is also applicable to late-stage functionalization of anti-inflammatory drugs, such as naproxen and ibuprofen, which enrich the chemical toolbox.

Lewis Acid-Catalyzed Selective Reductive Decarboxylative Pyridylation of N-Hydroxyphthalimide Esters: Synthesis of Congested Pyridine-Substituted Quaternary Carbons

A practical and efficient Lewis acid-catalyzed radical-radical coupling reaction of N-hydroxyphthalimide esters and 4-cyanopyridines with inexpensive bis(pinacolato)diboron as reductant has been developed. With ZnCl2 as the catalyst, a wide range of quaternary 4-substituted pyridines, including highly congested diarylmethyl and triarylmethyl substituents, could be selectively obtained in moderate to good yields with broad functional group tolerance. Combined theoretical calculations and experimental studies indicate that the Lewis acid could coordinate with the cyano group of the pyridine-boryl radical to lower the activation barrier of the C-C coupling pathway, leading to the formation of 4-substituted pyridines. Moreover, it could also facilitate the decyanation/aromatization of the radical-radical coupling intermediate.

Nickel-Catalyzed C(sp3)-H Arylation of Diarylmethane Derivatives with Aryl Fluorides

A novel nickel-catalyzed C(sp3)-H arylation with nonactivated aryl fluorides is reported. The use of 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (IMes) as a ligand was found to be critical to the success of the reaction. This new method enables the synthesis of a wide range of triarylmethane derivatives.

Light-Induced Alkylation of (Hetero)aromatic Nitriles in a Transition-Metal-Free C-C-Bond Metathesis

A light-induced C-C-σ-bond metathesis was achieved through transition-metal-free activation of an unstrained C(sp3)-C(sp3)-σ-bond in 1-benzyl-1,2,3,4-tetrahydroisoquinolines. A photoredox-mediated single-electron oxidation of these precursor amines yield radical cations which undergo a homolytic cleavage of a C(sp3)-C(sp3)-σ-bond rather than the well-known α-C-H-scission. The resulting carbon-centered radicals are used in the ipso-substitution of (hetero)aromatic nitriles proceeding through another single-electron transfer-mediated C-C-bond cleavage and formation.

Transition-Metal-Free Cross-Coupling of Aryl and N-Heteroaryl Cyanides with Benzylic Zinc Reagents

Functionalized 4-benzylated pyridines can be efficiently prepared by a transition-metal-free cross-coupling between various benzylic zinc chlorides and substituted 4-cyanopyridines in THF/DMPU under microwave irradiation (40 °C, 0.5-1.5 h). Selective benzylations on polycyano-aromatics have also been achieved under these mild conditions. We also report a novel oxidative nucleophilic substitution of a hydrogen on 1,3-dicyanobenzene using benzylic zinc reagents.

LDA-Mediated Synthesis of Triarylmethanes by Arylation of Diarylmethanes with Fluoroarenes at Room Temperature

A practical and convenient approach for the secondary C(sp3)-H arylation of diarylmethanes with various fluoroarenes is described. The reaction proceeds smoothly in the presence of LDA (lithium diisopropylamide) at room temperature and affords triarylmethanes in moderate to high yields.

Photoinduced direct 4-pyridination of C(sp3)-H Bonds

Direct substitution of hydrogen in C(sp3)-H bonds by 4-pyridine was achieved by employing benzophenone and 4-cyanopyridine in aqueous acetonitrile under photo-irradiating conditions. This simple and mild 4-pyridination proceeds in a highly chemoselective manner especially at benzylic C(sp3)-H bonds without affecting polar functional groups, and enables intermolecular formation of sterically hindered bonds between alkylaromatics and 4-pyridine. The present methodology thus serves as a powerful tool for construction of biologically active and functional molecules with 4-pyridine substructures.

Palladium-catalyzed direct arylation of aryl(azaaryl)methanes with aryl halides providing triarylmethanes

Direct arylation of aryl(azaaryl)methanes with aryl halidas takes place at the benzylic position in the presence of a hydroxide base under palladium catalysis to yield triarylmethanes

Superacid-catalyzed reactions of pyridinecarboxaldehydes

A variety of pyridinecarboxaldehydes are shown to give condensation products in high yields (80-99%, 10 examples) by reacting with benzene and CF3SO3H (triflic acid). In the superacidic solution, pyridinecarboxaldehydes can react with deactivated arenes (o-dichlorobenzene and nitrobenzene) and with saturated hydrocarbons (methylcyclohexane and adamantane). Dicationic intermediates from pyridinecarboxaldehydes in superacid (FSO3H-SbF5) have been directly observed using low temperature 13C NMR spectroscopy. Diprotonated pyridinecarboxaldehydes have also been studies using ab initio computational methods.