47090-47-1

Upstream product

• 110-86-1 pyridine 
• 100-44-7 benzyl chloride 
• 2402-78-0 2,6-dichloropyridine 
• 62673-31-8 benzyl(bromo)zinc 
• 626-05-1 2,6-Dibromopyridine 
• 1589-82-8 phenylmagnesium bromide 
• 6921-34-2 benzylmagnesium chloride 
• 100-39-0 benzyl bromide 
• 98-80-6 phenylboronic acid 
• 90678-57-2 2,6-bis(iodomethyl)pyridine 
• 101-82-6 2-Benzylpyridine 
• 100-52-7 benzaldehyde 

Downstream Products

• 1101197-07-2 cis-2,6-dibenzylpiperidine 

Relevant academic research and scientific papers

New Nickel-Based Catalytic System with Pincer Pyrrole-Functionalized N-Heterocyclic Carbene as Ligand for Suzuki-Miyaura Cross-Coupling Reactions

A new catalytic system with Ni(NO3)2·6H2O as the catalyst and a pincer pyrrole-functionalized N-heterocyclic carbene as the ligand was employed in the Suzuki-Miyaura cross-coupling reactions of aryl iodides with arylboronic acids. With 5 mol% catalyst, the catalytic reactions proceeded at 160 °C, giving coupling products in isolated yields of up to 94% in short reaction times (1-4 h). The system worked efficiently with aryl iodides bearing electron-donating or electron-withdrawing groups and arylboronic acids with electron-donating groups. Steric effects were observed for both aryl iodides and arylboronic acids. It is proposed that the reactions underwent a Ni(I)/Ni(III) catalytic cycle.

Bromide-promoted visible-light-induced reductive minisci reaction with aldehydes

Radical addition is a robust tool for bond formation. While ketyl radical reactivity of aldehydes by photoredox has been well-established, herein, we have now revealed a pathway for umpolung addition of aldehydes with or without external reductant. Hence,

Attenuation of London Dispersion in Dichloromethane Solutions

London dispersion constitutes one of the fundamental interaction forces between atoms and between molecules. While modern computational methods have been developed to describe the strength of dispersive interactions in the gas phase properly, the importance of inter-and intramolecular dispersion in solution remains yet to be fully understood because experimental data are still sparse in that regard. We herein report a detailed experimental and computational study of the contribution of London dispersion to the bond dissociation of proton-bound dimers, both in the gas phase and in dichloromethane solution, showing that attenuation of inter-and intramolecular dispersive interaction by solvent is large (about 70% in dichloromethane), but not complete, and that current state-of-The-Art implicit solvent models employed in quantum-mechanical computational studies treat London dispersion poorly, at least for this model system.

Suzuki-Miyaura and Negishi approaches to a series of forensically relevant pyridines and pyrimidines

A library of 5-aryl-4-methylpyrimidines, phenyl ring-substituted derivatives of 4-benzylpyrimidines, 2,6-benzylpyridines, and 2,6-dibenzyl-4-methylpyridines were prepared. The synthesis of 5-aryl-4-methylpyrimidines was accomplished by Suzuki-Miyaura cross-coupling reaction between arylboronic acids and 5-bromo-4-methylpyrimidine. The 4-benzylpyrimidines and 2,6-benzylpyridines were synthesized by treatment of 4-bromopyrimidine and 2,6-dibromopyridine derivatives with ring-substituted benzylzinc reagents. Georg Thieme Verlag Stuttgart.

Synthesis and evaluation of a series of homologues of lobelane at the vesicular monoamine transporter-2

A series of lobelane homologues has been synthesized and evaluated for their [3H]DTBZ binding affinity at the vesicular monoamine transporter-2 (VMAT2). The structure-activity relationships (SAR) indicate that for retention of binding affinity at VMAT2, the lengths of the methylene linkers should be no shorter than one methylene unit at C-6 of the piperidine ring, and no shorter than two methylene units at C-2 of the piperidine ring. These results indicate that the intramolecular distances between the piperidine ring and two phenyl rings in lobelane analogues are an important criterion for retention of high affinity at VMAT2.

Cobalt-catalyzed cross-coupling reaction of chloropyridines with grignard reagents

Treatment of 2-chloropyridine with benzylmagnesium chloride in the presence of a catalytic amount of cobalt(II) acetylacetonate in dioxane afforded the corresponding cross-coupling product in excellent yield. Trimethylsilylmethyl and phenyl Grignard reagents also participated in similar cross-coupling reactions.

SELECTIVE MONO-ALKYLATION AND ARYLATION OF AROMATIC DIHALIDES BY PALLADIUM-CATALYZED CROSS-COUPLING WITH THE GRIGNARD AND ORGANOZINC REAGENTS

Dibromobenzene, dibromothiophenes, dichloro- and dibromopyridine are highly selectively mono-alkylated and arylated with Grignard or organozinc reagents in the presence of palladium complexes as catalysts.