79445-44-6

Usage

Chemical composition

Composed of a pyridine ring attached to two 3,4-dimethoxyphenyl groups.

Usage

Commonly used as a ligand in coordination chemistry and catalysis, particularly in organometallic and inorganic chemistry.

Potential applications

Development of new organic materials, such as light-emitting diodes and organic photovoltaics.

Biological and medicinal properties

Shown potential as an antioxidant, anti-inflammatory agent, and anticancer activity.

Importance

Has diverse and important applications in various areas of chemistry and potential for further development in both chemical and biological sciences.

Upstream product

• 5029-67-4 2-iodopyridine 
• 91-16-7 1,2-dimethoxybenzene 
• 5460-32-2 1-iodo-3,4-dimethoxybenzene 
• 85311-89-3 2-pyridylcopper 
• 27012-25-5 5-bromo-2-phenylpyridine 
• 109-09-1 2-chloropyridine 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 109-04-6 2-bromo-pyridine 
• 895154-77-5 tris(3,4-dimethoxyphenyl)bismuthane 
• 118062-05-8 2,3,4-trimethoxyphenylboronic acid 
• 1243853-02-2 2-(2,3,4-trimethoxyphenyl)pyridine 
• 2859-78-1 4-Bromoveratrole 
• 109-76-2 Trimethylenediamine 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 

Downstream Products

• 1584705-73-6 2-(4,5-dimethoxy-2-(trifluoromethylthio)phenyl)pyridine 
• 875656-39-6 2-(3,4-dimethoxyphenyl)-piperidine hydrochloride 

Relevant academic research and scientific papers

Chromium-Catalyzed Reductive Cleavage of Unactivated Aromatic and Benzylic C-O Bonds

Reductive cleavage of aromatic and benzylic C-O bonds by chromium catalysis is reported. This deoxygenative reaction was promoted by low-cost CrCl 2precatalyst combined with poly(methyl hydrogen siloxane) as the mild reducing agent, providing a strategy in forming reduced motifs by cleavage of unactivated C-O bonds. A range of functional groups such as bromide, chloride, fluoride, hydroxyl, amino, and alkoxycarbonyl can be retained in the reduction.

Merging C-H Vinylation with Switchable 6π-Electrocyclizations for Divergent Heterocycle Synthesis

Pyridinium-containing polyheterocycles exhibit distinctive biological properties and interesting electrochemical and optical properties and thus are widely used as drugs, functional materials, and photocatalysts. Here, we describe a unified two-step strategy by merging Rh-catalyzed C-H vinylation with two switchable electrocyclizations, including aza-6π-electrocyclization and all-carbon-6π-electrocyclization, for rapid and divergent access to dihydropyridoisoquinoliniums and dihydrobenzoquinolines. Through computation, the high selectivity of aza-electrocyclization in the presence of an appropriate "HCl"source under either thermal conditions or photochemical conditions is shown to result from the favorable kinetics and symmetries of frontier orbitals. We further demonstrated the value of this protocol by the synthesis of several complex pyridinium-containing polyheterocycles, including the two alkaloids berberine and chelerythrine.

Directed Aromatic C-H Activation/Acetoxylation Catalyzed by Pd Nanoparticles Supported on Graphene Oxide

The first solid-supported directed aromatic C-H activation/acetoxylation has been successfully developed by using palladium nanoparticles supported on graphene oxide (PdNPs/GO) as a catalyst. The practicability of this method is demonstrated by simple preparation of catalyst, high catalytic efficiency, wide functional group tolerance, and easy scale up of the reaction. A hot filtration test and Hg(0) poisoning test indicate the heterogeneous nature of the catalytic active species.

Palladium-catalyzed C-H alkylation of 2-phenylpyridines with alkyl iodides

Palladium-catalyzed C-H alkylation reaction of 2-phenylpyridines with alkyl iodides has been successfully developed. The palladacycles obtained from 2-phenylpyridines should act as the key intermediates in the alkylation reaction.

Metal-free oxidative cyclization of acetophenones with diamines: A facile access to phenylpyridines

An efficient metal-free access to 2- and 3-phenylpyridines via oxidative coupling of acetophenones or phenylacetones with 1,3-diaminopropane has been described. The reaction involves shorter reaction time, excellent yields and a broad substrate scope. The reaction proceeds via the formation of imine, which further undergoes oxidative C-N bond cleavage, C-C bond formation and oxidation to give a pyridine skeleton. The quantum chemical calculations identified the transition state for the reaction and helped in tracing the reaction mechanism.

Cross-coupling study of iodo/chloropyridines and 2-chloroquinoline with atom-economic triarylbismuth reagents under Pd-catalysis

This study describes the palladium-catalyzed couplings of iodopyridines, chloropyridines, and chloroquinoline with atom-economic BiAr3 reagents in sub-stoichiometric loadings. Mono-arylations of iodo and chloropyridines produced arylpyridines i

Superstable palladium(0) complex as an air-and thermostable catalyst for Suzuki coupling reactions

An unprecedentedly thermo-and air-stable Pd0 complex from readily available electron-poor trifluoromethylated phosphine was serendipitously discovered. As detailed and comparative DFT calculations indicate, the stability of the complex is associated with unusually strong ligand-ligand noncovalent interactions. The unique stability and the presence of hydrophobic structural elements of the complex offer several practical advantages, which were exploited in catalytic Suzuki-Miyaura coupling reactions.

Copper-catalyzed aerobic synthesis of 2-arylpyridines from acetophenones and 1,3-diaminopropane

A copper-catalyzed reaction providing direct access to 2-arylpyridines from acetophenones and 1,3-diaminopropane is described. A range of electronically diverse acetophenones undergo this transformation, affording 2-arylpyridines in good yields. (Chemical Equation Presented).

Palladium-catalyzed trifluoromethylthiolation of aryl C-H bonds

A method for monotrifluoromethylthiolation of arenes via palladium-catalyzed directed C-H bond activation was described. The reaction was compatible with a variety of functional groups. Initial mechanistic studies disclosed that the turnover limiting step of the catalytic cycle did not involve C-H activation.

Triarylbismuthanes as threefold aryl-transfer reagents in regioselective cross-coupling reactions with bromopyridines and quinolines

Cross-coupling studies using bromopyridines and bromoquinolines with triarylbismuths as threefold coupling reagents in substoichiometric amounts under Pd-catalysed conditions are disclosed. The reactivity was high with both mono- and dibromopyridyl substrates, and mono- and bis-couplings were carried out regioselectively. A library of monoaryl and diaryl pyridines was formed in high yields. A one-pot strategy provided a simple and straightforward synthesis of both symmetrical and unsymmetrical diarylpyridines. Arylations of 2-bromo- and 3-bromoquinolines were achieved with triarylbismuth reagents. This study demonstrates that triarylbismuths may be used as threefold arylating reagents for the synthesis of aryl pyridines and quinolines through couplings with bromopyridines and bromoquinolines under Pd-catalysed conditions. Copyright