18103-80-5

Upstream product

• 2402-78-0 2,6-dichloropyridine 
• 201230-82-2 carbon monoxide 
• 98-80-6 phenylboronic acid 
• 626-05-1 2,6-Dibromopyridine 
• 5471-63-6 1,3-diphenylisobenzofuran 
• 100-52-7 benzaldehyde 
• 88-67-5 2-Iodobenzoic acid 
• 832-81-5 3-phenyl-[1,2,3]triazolo[1,5-a]pyridine 
• 108-90-7 chlorobenzene 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 1008-89-5 2-phenylpyridine 
• 109-72-8 n-butyllithium 
• 611-74-5 N,N-dimethylbenzamide 

Downstream Products

• 1403850-07-6 [N-((2-phenylpyridine-6-yl)phenylmethylene)-2,6-diisopropylaniline]NiBr₂ 
• 58088-71-4 phenyl(6-phenylpyridin-2-yl)methanamine 

Relevant academic research and scientific papers

Site-selective c-h acylation of pyridinium derivatives by photoredox catalysis

A strategy for visible-light-induced site-selective C-H acylation of pyridinium salts was developed by employing N-methoxy-or N-aminopyridinium salts, offering a powerful synthetic tool for accessing highly valuable C2- A nd C4-acylated pyridines. The met

Pd-Catalyzed regioselective synthesis of 2,6-disubstituted pyridines through denitrogenation of pyridotriazoles and 3,8-diarylation of imidazo[1,2-a] pyridines

Synthesis of 2,6-disubstituted pyridines from pyridotriazoles through palladium-catalyzed aerobic oxidative denitrogenative reactions has been described. Denitrogenation of arylated pyridotriazoles generates metal-carbene intermediates in situ and provides selectively 6-aryl-2-benzoylpyridines. The same conditions have been extended to regioselective C-3 and C-8 diarylation of several imidazo[1,2-a]pyridines.

Visible-light-initiated catalyst-free oxidative cleavage of (Z)-triaryl-substituted alkenes containing pyridyl motif under ambient conditions

The catalyst-free oxidative cleavage of (Z)-triaryl-substituted alkenes bearing a pyridyl motif in ambient air under the irradiation of blue LEDs at room temperature has been developed. The reaction was facile and scalable, and proceeded with good functional group tolerance, affording pharmaceutically useful 2-acyl pyridines. The electron paramagnetic resonance (EPR) studies together with control experiments showed that the singlet oxygen (1O2) and superoxide anion (O2˙?) are the reactive oxidants. The1O2generation mechanism correlated well with the photophysical properties of the substrate (Z)-triaryl-substituted alkenes, the excited state of which was proved to serve as the triplet sensitizer for the generation of1O2

Ni(II) complexes with ligands derived from phenylpyridine, active for selective dimerization and trimerization of ethylene

An electrophilic substitution-carbonylation reaction on phenylpyridine based on the concept of 'umpolung' was used to prepare a series of pyridine based carbonyl compounds and bispyridine derivatives. The key intermediate which enhances this reaction is a base aggregate formed by the association of BuLi with lithium 2-dimethylaminoethanolate (LiDMAE) which is stabilized in nonpolar solvents. The presence of polar chelating amides that are used as acyl donors was found to collapse the superbase aggregates liberating nucleophilic 'free' BuLi. These nucleophiles lead a classical nucleophilic reaction to introduce butyl tails on the pre-ligand molecules. Pyridine carbonyl compounds produced by these electrophilic substitution-carbonylation reactions, on treatment with 2,6-diisopropylaniline and (DME)NiBr2 in glacial acetic acid at reflux temperature, gave Ni(II) complexes in good yields in a one pot protocol. These complexes are active toward ethylene, producing selective dimerization and trimerization products.

Palladium-N-heterocyclic carbene an efficient catalytic system for the carbonylative cross-coupling of pyridine halides with boronic acids

Carbonylative cross-coupling of different pyridyl halides with various boronic acids was studied using catalytic systems constituted of N-heterocyclic carbene type ligands and palladium. These systems easily obtained in situ from the corresponding imidazolium salt and palladium acetate appear more efficient toward bromopyridines than catalysts based on hindered and basic alkylphosphines such as tricyclohexylphosphine. Their higher efficiency was also evidenced by coupling using chloro- or dichloropyridines and chloroquinolines, which practically do not react with catalytic systems based on phosphines.

Palladium-catalyzed carbonylative coupling of pyridine halides with aryl boronic acids

The carbonylative Suzuki cross-coupling of a variety of mono-iodopyridines and bromopyridines (1a,b, 3a-c, 5) catalyzed by palladium-phosphane systems has been studied to prepare benzoylpyridine derivatives (2, 4, 6). The selectivity and the rate of the reaction are highly dependent on the reaction conditions, i.e. nature of the palladium catalyst precursor, solvent, temperature and CO pressure. The main side-products arise from direct, non-carbonylative cross-coupling. Under optimized conditions, benzoylpyridines are recovered in high yields (80-95%). The order of reactivity decreases from iodo- to bromopyridines and from 2-, 4- to 3-substituted halopyridines. The reactivity of dihalopyridines has been investigated; 2,6-dibromopyridine (7) and 3,5-dibromopyridine (11) are selectively transformed into either the corresponding benzoyl-phenylpyridine (8, 12) or the corresponding dibenzoylpyridine (9, 13). Dissymmetric 2,5-dihalopyridines (15a,b) are transformed into 2-benzoyl-5-bromopyridine (16) or 2,5-dibenzoylpyridine (17) in high yields.

Direct Synthesis of Benzoylpyridines from Chloropyridines via a Palladium-Carbene Catalyzed Carbonylative Suzuki Cross-Coupling Reaction

The use of N-heterocyclic carbene-type ligands with palladium catalysts allows the activation of chloropyridines and chloroquinoline towards carbonylative cross-coupling with phenylboronic acid for the synthesis of unsymmetrical biaryl ketones.

Palladium-catalyzed carbonylative cross-coupling reactions of pyridine halides and aryl boronic acids: A convenient access to α-pyridyl ketones

The proper choice of solvent, catalyst precursor and CO pressure enables the easy and selective transformation of mono- and dihalopyridines into phenyl pyridyl ketones in 81-95% yields.