5024-68-0

Usage

InChI:InChI=1/C11H10N2/c1-2-5-10(6-3-1)13-11-7-4-8-12-9-11/h1-9,13H

Upstream product

• 462-08-8 pyridin-3-ylamine 
• 591-50-4 iodobenzene 
• 626-60-8 3-Chloropyridine 
• 62-53-3 aniline 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 329214-79-1 3-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 25288-46-4 2-phenoxy-N-(pyridin-3-yl)acetamide 
• 587-65-5 N-chloroacetyl-aniline 
• 78205-18-2 2-chloro-N-(pyridine-3-yl)acetamide 
• 108-86-1 bromobenzene 
• 98-80-6 phenylboronic acid 
• 626-55-1 3-Bromopyridine 
• 32848-20-7 3-pyridyl nonaflate 

Downstream Products

• 1268526-13-1 C₂₂H₃₀N₂ 
• 1268526-29-9 1-methyl-3-(phenylamino)pyridinium iodide 
• 1380492-21-6 3-(phenylamino)-1-(propan-2-yl)pyridin-1-ium iodide 
• 1380492-17-0 3-(phenylamino)-1-(propan-2-yl)pyridin-1-ium tosylate 
• 1380492-18-1 C₁₄H₁₆N₂ 
• 100240-05-9 3-(phenylamino)piperidine 
• 1310693-29-8 5-(5-cyclohexylpentyl)-1-methyl-5H-pyrido[3,2-b]indol-1-ium iodide 
• 124082-95-7 Butyl-pyridin-3-yl-(2,4,6-trichloro-phenyl)-amine 

Relevant academic research and scientific papers

Mediator-Enabled Electrocatalysis with Ligandless Copper for Anaerobic Chan-Lam Coupling Reactions

Simple copper salts serve as catalysts to effect C-X bond-forming reactions in some of the most utilized transformations in synthesis, including the oxidative coupling of aryl boronic acids and amines. However, these Chan-Lam coupling reactions have historically relied on chemical oxidants that limit their applicability beyond small-scale synthesis. Despite the success of replacing strong chemical oxidants with electrochemistry for a variety of metal-catalyzed processes, electrooxidative reactions with ligandless copper catalysts are plagued by slow electron-transfer kinetics, irreversible copper plating, and competitive substrate oxidation. Herein, we report the implementation of substoichiometric quantities of redox mediators to address limitations to Cu-catalyzed electrosynthesis. Mechanistic studies reveal that mediators serve multiple roles by (i) rapidly oxidizing low-valent Cu intermediates, (ii) stripping Cu metal from the cathode to regenerate the catalyst and reveal the active Pt surface for proton reduction, and (iii) providing anodic overcharge protection to prevent substrate oxidation. This strategy is applied to Chan-Lam coupling of aryl-, heteroaryl-, and alkylamines with arylboronic acids in the absence of chemical oxidants. Couplings under these electrochemical conditions occur with higher yields and shorter reaction times than conventional reactions in air and provide complementary substrate reactivity.

In-vitro evaluation of antioxidant and anticholinesterase activities of novel pyridine, quinoxaline and s-triazine derivatives

Cholinesterase enzymes such as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) cause hydrolysis of acetylcholine (ACh), a neurotransmitter responsible for the cognitive functions of the brain such as acquiring knowledge and comprehension. Th

Sterically enriched bulky 1,3-bis(: N, N ′-aralkyl)benzimidazolium based Pd-PEPPSI complexes for Buchwald-Hartwig amination reactions

Pd-PEPPSI (palladium-pyridine enhanced pre-catalyst preparation stabilization and initiation) complexes are now emerging as well-defined catalysts for C-C and C-N bond formation. In connection with this, we prepared a family of six air and moisture stable

Ullmann-type: N-arylation of anilines with alkyl(aryl)sulfonium salts

A palladium/copper-cocatalyzed Ullmann-type N-arylation of anilines using alkyl(aryl)sulfonium triflates as arylation reagents has been accomplished. The reaction enabled Caryl-S bond cleavage over Calkyl-S bond breakage of alkyl(aryl)sulfoniums by Pd(P(tBu)3)2/CuI and gave the corresponding N-arylated products in good to high yields. It was also significant that the reactions of aniline with asymmetric butyl(mesityl)(aryl)sulfonium triflates showed excellent selectivity, in which the aryl groups other than the bulky and electron-rich mesityl moieties were transformed.

Allyl complexes for use in coupling reactions

A complex of formula (1), wherein, M is palladium or nickel, R1 and R2 are independently organic groups having 1-20 carbon atoms, or R1 and R2 are linked to form a ring structure with the phosphorus atom, R3 is selected from the group consisting of substituted and unsubstituted aryl, substituted and unsubstituted heteroaryl, and substituted and unsubstituted metallocenyl, R4 is an organic group having 1-20 carbon atoms, n is 0, 1, 2, 3, 4 or 5, X is an anionic ligand. A process for the preparation of the complex, and its use in carbon-carbon or carbon-nitrogen coupling reactions is also provided.

PHOSPHINE COMPOUND, CROSSLINKED COMPOSITION, AND MANUFACTURING METHOD OF AROMATIC AMINE COMPOUND

PROBLEM TO BE SOLVED: To provide a phosphine compound capable of constituting a transition metal complex excellent in reaction speed and selectivity as a catalyst. SOLUTION: There is provided a phosphine compound represented by the formula (I). In the formula Ar represents each independently an aryl group which may be substituted, R1 represents each independently a linear, branched or cyclic alkyl group, R2 represents each independently a linear, branched or cyclic alkyl group, alkoxy group or aryl group which may be substituted, or neighboring 2 R2 are bound each other to form a ring, and n represents an integer of 0 to 4. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Mixed er-NHC/phosphine Pd(ii) complexes and their catalytic activity in the Buchwald-Hartwig reaction under solvent-free conditions

A series of novel (NHC)PdCl2-PR3 complexes were synthesized and fully characterized by 1H, 13C, 31P NMR and FT-IR spectroscopy. These complexes showed high catalytic activity toward solvent-free Buchwald-Hartwig amination. Both primary and secondary amines were efficiently utilized under the same reaction conditions. The solvent-free synthesis of valuable N-aryl carbazoles and similar N-heterocyclic systems was described.

NIXANTPHOS: A highly active ligand for palladium catalyzed Buchwald-Hartwig amination of unactivated aryl chlorides

Xantphos is one of the two most common ligands used in palladium catalyzed Buchwald-Hartwig amination reactions, because of its broad scope and high probability of success. It does not, however, work well with unactivated aryl chlorides. Herein NIXANTPHOS is compared to Xantphos and an array of mono- and bidentate phosphines. NIXANTPHOS outperforms Xantphos and all other bidentate ligands examined. Under the optimal reaction conditions, unactivated aryl chlorides afford the expected products in good to excellent yield with as low as 0.05 mol% (500 ppm) palladium loading.

Spectroscopic Studies of the Chan-Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity

We report an investigation of the Chan-Lam amination reaction. A combination of spectroscopy, computational modeling, and crystallography has identified the structures of key intermediates and allowed a complete mechanistic description to be presented, including off-cycle inhibitory processes, the source of amine and organoboron reactivity issues, and the origin of competing oxidation/protodeboronation side reactions. Identification of key mechanistic events has allowed the development of a simple solution to these issues: manipulating Cu(I) → Cu(II) oxidation and exploiting three synergistic roles of boric acid has allowed the development of a general catalytic Chan-Lam amination, overcoming long-standing and unsolved amine and organoboron limitations of this valuable transformation.

Empirical and Computational Insights into N-Arylation Reactions Catalyzed by Palladium meta-Terarylphosphine Catalyst

An in situ generated Pd–Cy*Phine catalyst has been successfully applied to the N-arylation of primary and secondary amines, and it exhibited high performance across multiple substrate classes. The performance induced by the meta-terarylphosphine motif of the Cy*Phine ligand for C?N cross-coupling displayed only subtle differences to that of its biarylphosphine congener XPhos. DFT studies demonstrated comparable reaction energetics in the catalytic cycle steps for both Pd–Cy*Phine and Pd–XPhos, which was consistent with previous findings. The computational investigation also indicated that a putative rate-determining step occurred after amine binding, which was likely to have annulled the expected benefits of having a meta-terarylphosphine ligand architecture.