1173294-82-0

Upstream product

• 5957-90-4 4-(2-pyridinyl)anisole 
• 100-52-7 benzaldehyde 
• 2835-06-5 phenylglycin 
• 100-47-0 benzonitrile 
• 74542-54-4 N,N-phenyl-p-toluenesulfonylbenzamide 
• 100-42-5 styrene 
• 536-74-3 phenylacetylene 
• 96-09-3 styrene oxide 
• 100-44-7 benzyl chloride 
• 611-71-2 MANDELIC ACID 
• 100-46-9 benzylamine 
• 108-88-3 toluene 
• 673-32-5 1-Phenylprop-1-yne 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 1024585-98-5 2-(5-methoxy-[1,1′-biphenyl]-2-yl)pyridine 

Relevant academic research and scientific papers

A Strategy for Amide C-N Bond Activation with Ruthenium Catalyst: Selective Aromatic Acylation

A strategy for amide C-N bond activation with ruthenium catalyst is described for the first time. The in situ formed bis-cycloruthenated complexes were demonstrated to be the key active species with superior oxidative addition ability to an inert amide C-N bond. The direct C-H bond activation of 2-arylpyridines followed by the amide C-N bond activation took place in the presence of a ruthenium precatalyst to produce monoacylation products in moderate to good yields. Synthetically useful functional groups, such as halogen atoms (F and Cl), ester, acetyl, and vinyl, remained intact during tandem C-H/C-N bond activation reactions.

Preparation method of nitrogen-containing heterocyclic diarylketone compound

The invention belongs to the technical field of pharmaceutical and chemical intermediates and related chemistry, and provides a preparation method of a nitrogen-containing heterocyclic diarylketone compound. According to the method, N,N-phenyl p-toluenesulfonyl benzamide and derivatives thereof are used as acylation reagents and are subjected to a C-H acylation reaction with a 2-phenylpyridine compound in an anhydrous organic solvent under the action of a metal catalyst, a ligand, carboxylic acid and an alkali to be converted into the nitrogen-containing heterocyclic diarylketone compound. According to the preparation method of the nitrogen-containing heterocyclic diarylketone compound, reaction steps are few, amide widely existing in the nature is used as an acyl source, and the nitrogen-containing heterocyclic diarylketone compound is environmentally friendly, low in price, mild in reaction condition and convenient to operate; and the target product is obtained with high yield and high selectivity, and the method has good industrial production value and practical application value. The diarylketone compound synthesized by the method can be subjected to further functionalization reaction, and can be widely applied to the fields of synthesis of medicines, pesticides, bioactive molecules, functional material molecules and the like.

Monodisperse CuPd alloy nanoparticles as efficient and reusable catalyst for the C (sp2)–H bond activation

Metal-catalyzed selective activation of C–H bonds is very important for the construction of a variety of biologically active molecules. Supported alloy nanoparticles are of great interest in various catalytic applications due to the synergistic effects between different metals. Here, well-dispersed CuPd alloy nanoparticles supported on reduced graphene oxide (rGO) were synthesized and found to be highly efficient and recyclable catalyst for the chelation-assisted C (sp2)–H bond activation. Aromatic ketones or esters were synthesized via the cross-dehydrogenative coupling (CDC) reaction between 2-arylpyridines and alcohols or acids. Moreover, the catalyst was recovered and used for five times without significantly losing activity.

Pyridine-directed carbon–carbon single bond activation: Rhodium-catalyzed decarbonylation of aryl and heteroaromatic ketones

The decarbonylation of 2-pyridyl-substituted ketones via transition metal-catalyzed carbon–carbon bond activation provides ready access to a variety of biaryl compounds. The highly efficient and general method provides reliable decarbonylation of benzophenones including a range of functional groups and substitution patterns. The methodology has also proven highly efficient for heteroaromatic substrates, including those containing thiophenyl, indolyl, quinolinyl, and pyridine substitution.

Ag1Pd1-rGO nanocomposite as recyclable catalyst for CDC reactions of 2-arylpyridines with aldehydes

Ag1Pd1 nanoparticle-reduced graphene oxide (Ag1Pd1-rGO) nanocomposite was used as an efficient catalyst for the synthesis of aromatic ketones via cross dehydrogenative coupling (CDC) reactions of 2-arylpyridines

Use of Cyclopropane as C1 Synthetic Unit by Directed Retro-Cyclopropanation with Ethylene Release

Cyclopropanation of alkenes is a well-established textbook reaction for the synthesis of cyclopropanes, where a "high-energy" carbene species is exploited to drive the reaction forward. However, little attention has been focused toward molecular transformations involving the reverse reaction, retro-cyclopropanation (RC). This is because of difficulties associated with both cleaving the two geminal C-C single bonds and exploiting the generated carbenes for further transformations in an efficient and selective manner. Here, we report that a molybdenum-based catalytic system overcomes the above challenges and effects the RC of cyclopropanes bearing a pyridyl group with the release of ethylene (alkene) and the subsequent intramolecular cyclization leading to pyrido[2,1-a]isoindoles. The reaction allows for the uncommon use of cyclopropanes as C1 synthetic units in contrast to most conventional reactions in which cyclopropanes are used as C3 synthetic units. We anticipate that this new strategy will pave the way for C1 cyclopropane chemistry.

Preparation method of 2-(2-benzoyl)phenyl pyridines compound

The invention relates to a preparation method of a 2-(2-benzoyl)phenyl pyridines compound. The preparation method comprises the following steps: adding 5 mol percent of a catalyst PdCl2, 10 mol percent of a phosphine ligand XPhos, 0.3mmol of a reactant I,

Palladium-catalyzed decarboxylative, decarbonylative and dehydrogenative C(sp2)-H acylation at room temperature

Over the past few decades, an impressive array of C-H activation methodology has been developed for organic synthesis. However, due to the inherent inertness of the C-H bonds (e.g. ～110 kcal mol-1 for the cleavage of C(aryl)-H bonds) harsh reaction conditions have been realized to overcome high energetic transition states resulting in a limited substrate scope and functional group tolerance. Therefore, the development of mild C-H functionalization protocols is in high demand to exploit the full potential of the C-H activation strategy in the synthesis of a complex molecular framework. Although, electron-rich substrates undergo electrophilic metalation under relatively mild conditions, electron-deficient substrates proceed through a rate-limiting C-H insertion under forcing conditions at high temperature. In addition, a stoichiometric amount of toxic silver salt is frequently used in palladium catalysis to facilitate the C-H activation process which is not acceptable from the environmental and industrial standpoint. We report herein, a Pd(ii)-catalyzed decarboxylative C-H acylation of 2-arylpyridines with α-ketocarboxylic acids under mild conditions. The present protocol does not require stoichiometric silver(i) salts as additives and proceeds smoothly at ambient temperature. A novel decarbonylative C-H acylation reaction has also been accomplished using aryl glyoxals as acyl surrogates. Finally, a practical C-H acylation via a dehydrogenative pathway has been demonstrated using commercially available benzaldehydes and aqueous hydroperoxides. We also disclose that acetonitrile solvent is optimal for the acylation reaction at room temperature and has a prominent role in the reaction outcome. Control experiments suggest that the acylation reaction via decarboxylative, decarbonylative and dehydrogenative proceeds through a radical pathway. Thus we disclose a practical protocol for the sp2 C-H acylation reaction.

Polystyrene-supported Pd(II) complex-catalysed carboacylation of 2-arylpyridines with alcohols via C─H bond activation under solvent-free conditions

Polystyrene-supported N,N-dimethylethylenediamine Pd(II) complex C was used as an efficient catalyst for the synthesis of aromatic ketones via ortho-acylation of sp2 C─H bonds of 2-arylpyridines with alcohols as effective coupling partners. The alcohols were oxidized with tert-butyl hydroperoxide to their corresponding aldehydes in situ and efficiently coupled with 2-arylpyridines to form aryl ketones under solvent-free conditions. Furthermore, catalyst C could be easily recovered by simple filtration and reused for five cycles without any significant decrease in its activity.

Polystyrene supported Dichloro-(8-aminoquinoline)-Palladium(II) complex catalyzed C[sbnd]H bond activation for ortho-acylation of 2-aryl pyridines

Polystyrene-supported Dichloro-(8-aminoquinoline)-Pd(II) complex C was synthesized and its catalytic efficiency was evaluated for ortho-acylation of 2-aryl pyridines with alcohols to form aryl ketones via cross dehydrogenative coupling. In addition in the presence of Pd(II) complex, toluene derivatives were also employed as an effective coupling partner for synthesis of aromatic ketones. Furthermore, this catalyst was highly stable and could be easily recovered by simple filtration and reused for four cycles with no significant decrease in its activity and selectivity.