25363-55-7

Upstream product

• 100-66-3 methoxybenzene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 1003-68-5 5-methyl-pyridin-2-ol 
• 18368-58-6 2-mercapto-5-methylpyridine 
• 623-12-1 4-chloromethoxybenzene 
• 1101205-22-4 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 3510-66-5 2-Bromo-5-methylpyridine 
• 155959-01-6 5-chloro-3-(4-methoxyphenyl)-6-methyl-2H-1,4-oxazin-2-one 
• 78-85-3 2-methylpropenal 
• 7596-36-3 1-(2-(4-methoxyphenyl)-2-oxoethyl)pyridin-1-ium iodide 
• 463297-59-8 2-chloro-6-(4-methoxy-phenyl)-3-methyl-pyridine 
• 18368-64-4 2-chloro-5-methylpyridine 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 

Downstream Products

• 463297-61-2 5-bromomethyl-2-(4-methoxy-phenyl)-pyridine 
• 1258844-09-5 Pt(II)(5-methyl-2-(4-methoxyphenyl)-pyridine)(5-methyl-2-(4-methoxyphenyl)-pyridine(-1H))Cl 

Relevant academic research and scientific papers

Luminescent cyclometalated dialkynylgold(III) complexes of 2-phenylpyridine-type derivatives with readily tunable emission properties

A novel class of luminescent dialkynylgold(III) complexes containing various phenylpyridine and phenylisoquinoline-type bidentate ligands has been successfully synthesized and characterized. The structures of some of them have also been determined by X-ray crystallography. Electrochemical studies demonstrate the presence of a ligand-centered reduction originating from the cyclometalating C^N ligand, whereas the first oxidation wave is associated with an alkynyl ligand-centered oxidation. The electronic absorption and photoluminescence properties of the complexes have also been investigated. In dichloromethane solution at room temperature, the low-energy absorption bands are assigned as the metal-perturbed π-π* intraligand (IL) transition of the cyclometalating C^N ligand, with mixing of charge-transfer character from the aryl ring to the pyridine or isoquinoline moieties of the cyclometalating C^N ligand. The low-energy emission bands of the complexes in fluid solution at room temperature are ascribed to originate from the metal-perturbed π-π* IL transition of the cyclometalatng C^N ligand. For complex 4 that contains an electron-rich amino substituent on the alkynyl ligand, a structureless emission band, instead of one with vibronic structures as in the other complexes, was observed, which was assigned as being derived from an excited state of a [π(Ci￡CC6H 4NH2)→π (C^N)] ligand-to-ligand charge-transfer (LLCT) transition. Luminescence enhancement: A novel class of luminescent dialkynylgold(III) complexes containing various phenylpyridine- and phenylisoquinoline-type bidentate ligands has been successfully synthesized and characterized. This class of complexes has been shown to demonstrate rich and tunable photoluminescence properties (see picture).

Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions

Heteroaromatic sulfinates are effective nucleophilic reagents in Pd0-catalyzed cross-coupling reactions with aryl halides. However, metal sulfinate salts can be challenging to purify, solubilize in reaction media, and are not tolerant to multi-step transformations. Here we introduce base-activated, latent sulfinate reagents: β-nitrile and β-ester sulfones. We show that under the cross-coupling conditions, these species generate the sulfinate salt in situ, which then undergo efficient palladium-catalyzed desulfinative cross-coupling with (hetero)aryl bromides to deliver a broad range of biaryls. These latent sulfinate reagents have proven to be stable through multi-step substrate elaboration, and amenable to scale-up.

Rhodium-Catalyzed Additive-Free C?H Ethoxycarbonylation of (Hetero)Arenes with Diethyl Dicarbonate as a CO Surrogate

A rhodium-catalyzed C(sp2)-H ethoxycarbonylation of indoles and arylpyridines using diethyl dicarbonate was developed. The catalytic process features an additive-free ethoxycarbonylation reaction, in which only ethanol and CO2 are produced as byproducts, providing a CO-free and operationally simple protocol. The introduced ethoxycarbonyl group is easily transformed into other ester and amide functionalities in a single step. Moreover, the reaction can be successfully applied on gram scale, and allows for the efficient synthesis of indole-2-carboxylic acid esters and isophthalates.

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.

Efficient construction of C–C bonds from aryl halides/aryl esters with arylboronic acids catalysed by palladium(II) thiourea complexes

A new set of palladium(II) complexes comprising phenyl(thiazolyl)thiourea ligands have been successfully synthesized and characterized with the aid of analytical as well as spectral (IR, UV–visible and NMR) methods. A distorted square-planar geometry with N^S coordination mode of thiourea ligands in the new palladium complexes was corroborated by single-crystal X-ray diffraction methods. Interestingly, the palladium(II) thiourea complexes showed the highest catalytic activity with 0.1 mol% catalyst loading in Suzuki–Miyaura cross-coupling reactions utilizing a range of aryl bromides/unactivated aryl chlorides with arylboronic acids as coupling partners in aqueous–organic media. Syntheses of diaryl ketones using aryl esters and arylboronic acids as coupling partners were also achieved with low catalyst loading within 20 h. The potential of our catalyst was demonstrated by its wide substrate scope, low catalyst loadings and high isolated yield. Moreover, the influences of key parameters like solvent, base, temperature and catalyst loading were also investigated.

Suzuki-Miyaura cross-coupling for efficient synthesis of aryl-substituted N-heteroarenes catalyzed by recyclable N-phenylpiperazine-Palladium(II) complex

Polystyrene supported N-phenylpiperazine-Pd(II) complex D was synthesized and characterized by various techniques, including Fourier transform infrared spectroscopy (FTIR), scanning electronmicroscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and thermal analysis (TG-DTA). This heterogeneous Pd(II) complex showed high catalytic efficiency for the Suzuki-Miyaura coupling of arylboronic acids with aryl bromides, aryl chlorides to give the corresponding 2-arylpyridines and heteroarenes. The coupled products were formed in excellent yields at low catalyst loadings under mild reaction conditions. Further, this heterogeneous catalyst showed excellent recyclability and reused for four cycles with no significant decrease in its activity.

Highly efficient palladium(II) hydrazone based catalysts for the Suzuki coupling reaction in aqueous medium

Synthesis of a new family of air stable palladium(ii)benzhydrazone complexes of the general formula [PdCl(PPh3)(L)] (where HL = thiophene aldehyde benzhydrazones) incorporating PPh3 and chloride as co-ligands has been described through a single and convenient step with good yields. All the new complexes have been fully characterized by means of elemental analysis, IR, UV-vis, and NMR spectral methods. The molecular structures of three of the complexes were determined by single crystal X-ray crystallography, which confirm the coordination mode of benzhydrazone and reveal the presence of a distorted square planar geometry around the Pd ion. The complexes 1-5 (0.05 mol%) have been found to be a highly active catalytic system in the mono and double Suzuki-Miyaura cross coupling reaction of deactivated aryl and heteroaryl bromides with different types of aryl boronic acids in neat water and the maximum yield was up to >99%. Notably, these catalysts work well with ultra-low loading of the catalysts and show high turnover numbers in a short time towards different substrates. Moreover, the catalysts could be simply recovered and reused five times without significant loss of efficiency.

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

Direct arylation of n-heteroarenes with aryldiazonium salts by photoredox catalysis in water

A highly effective visible light-promoted "radical-type" coupling of N-heteroarenes with aryldiazonium salts in water has been developed. The reaction proceeds at room temperature with [Ru(bpy)3]Cl 2×6 H2O as a photosensit

Direct arylation of pyridines without the use of a transition metal catalyst

A method for achieving the direct arylation of pyridines with phenylhydrazine hydrochloride was developed in this study. This new reaction proceeds readily at room temperature without the use of any transition metal catalysts. This method allows rapid access to various arylated heterocycles that are more difficult to access through traditional methods.