16344-79-9

Upstream product

• 109-04-6 2-bromo-pyridine 
• 768-60-5 4-methoxyphenylacetylen 
• 1945-84-2 2-ethynylpyridine 
• 696-62-8 para-iodoanisole 
• 18438-38-5 2-methylsulfanyl-pyridine 
• 109-09-1 2-chloropyridine 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 182815-94-7 2-(2,2-dibromovinyl)-pyridine 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 5029-67-4 2-iodopyridine 
• 86521-05-3 2-(trimethylsilylethynyl)pyridine 

Downstream Products

• 710946-95-5 2-[5-(4-methoxy-phenyl)-2H-[1,2,3]triazol-4-yl]-pyridine 
• 1006057-77-7 2-(4-methoxyphenyl)-3-pyridin-2-yl-1H-indole-6-carboxylic acid methyl ester 
• 1006057-69-7 3-(4-methoxyphenyl)-2-pyridin-2-yl-1H-indole-6-carboxylic acid methyl ester 
• 40061-36-7 1-(4-methoxyphenyl)-2-(pyridine-2-yl)ethane-1,2-dione 
• 906753-69-3 1-(but-3-enyl)-2-(4-methoxy-phenyl-ethynyl)-pyridinium triflate 
• 1569271-19-7 C₂₄H₂₆Cl₂IrNO 
• 710947-00-5 4-[4-(4-methoxy-phenyl)-5-pyridin-2-yl-[1,2,3]triazol-2-ylmethyl]-benzonitrile 
• 710947-11-8 4-[4-(4-methoxy-phenyl)-5-pyridin-2-yl-[1,2,3]triazol-2-yl]-benzonitrile 

Relevant academic research and scientific papers

Stereo- and regioselective gold(i)-catalyzed hydroamination of 2-(arylethynyl)pyridines with anilines

The gold-catalyzed hydroamination of 2-(arylethynyl)pyridines with anilines affords stereoselectively Z-enamine products with excellent regioselectivity. The reaction proceeds with moderate to excellent yields and accommodates a diverse range of functional groups on alkynes (ether, bromo, trifluoromethyl, acetyl, and carbomethoxy) and anilines (ether, bromo, chloro, and carbethoxy). The stereochemistry of the obtained enamines is complementary to that reported in previous studies. A plausible explanation for the observed selectivity was attained by means of NMR experiments.

Sonogashira Cross-Coupling of Aryltrimethylammonium Salts

A protocol for C(sp)-C(sp2) bond formation via the Sonogashira coupling reaction involving C-N bond cleavage with aryltrimethylammonium triflate as an electrophilic coupling partner is described in this work. The reactions proceeded well under mild conditions with a stoichiometric ratio of alkyl, aryl, or heteroaryl acetylenes and provided yields of up to 93%. Numerous useful functional groups were tolerated under the reaction conditions. Direct amine alkynylation can be achieved through a one-pot process without the isolation of ammonium salt. The protocol can be performed on a gram scale. Density functional theory calculations were performed to investigate the reaction mechanism that involved oxidative addition, alkyne coordination, deprotonation, and reductive elimination, which yielded the cross-coupling product.

Method for synthesizing phenylethynyl pyridine derivative

The invention discloses a method for synthesizing a phenylethynyl pyridine derivative. The method takes palladium acetate as a catalyst, 4,5-bisdiphenylphosphine-9,9-dimethoxyxanthene as a ligand andmethanol as a solvent; 2-iodopyridine and a phenylacetylene type compound are coupled to prepare the phenylethynyl pyridine derivative. The method disclosed by the invention has the advantages of simplicity in operation, efficient reaction, moderate conditions and good substrate applicability and can be widely used for preparing the phenylethynyl pyridine derivative.

Silver-Catalysed Domino Approach to 1,3-Dicarbo-Substituted Isochromenes

We report herein the first example of the silver triflate catalysed synthesis of 1,3-dicarbo-substituted isochromene derivatives starting from 2-alkynyl(hetero)arylaldehydes and enolizable ketones. The reaction proceeds in a cascade fashion under mild heating with complete regioselectivity and moderate-to-good yields. In some cases, the reaction gives unexpected homodimeric products. Two competitive mechanistic paths for the formation of the desired isochromene derivatives and the homodimeric products are described.

An N-heterocyclic carbene based MOF catalyst for Sonogashira cross-coupling reaction

The post-synthetic modification of azolium containing MOFs generated a new heterogeneous N-heterocyclic carbene catalyst (1-Pd), which is very active for Sonogashira cross coupling reaction.

Post-synthetic modified MOF for Sonogashira cross-coupling and Knoevenagel condensation reactions

A new heterogeneous NHC catalyst (1-Pd) was obtained by the post-synthetic modification of an azolium-containing metal-organic framework (1) which was synthesized by solvothermal reaction of 1,3-bis(4-carboxyphenyl)imidazolium chloride (H2L+Cl?) and Zn(NO3)2·6H2O. This new material, 1-Pd, was characterized by PXRD, TGA, SEM, TEM, 1H and 13C NMR, FTIR and XPS measurements. This catalyst exhibited an excellent activity for both Sonogashira cross-coupling and Knoevenagel condensation reaction retaining its catalytic and uniform distribution of the active sites, palladium (II) anchored on N-heterocyclic carbene (NHC-Pd(II)), for at least four cycles without losing its structural integrity.

Sonogashira couplings catalyzed by collaborative (N-heterocyclic carbene)-copper and -palladium complexes

A general protocol for the Sonogashira reaction using a 100:1 combination of (N-heterocyclic carbene)-Cu and (N-heterocyclic carbene)-Pd complexes is presented. Catalyst loadings of 1 mol % (NHC)-Cu and 0.01 mol % (NHC)-Pd allow for the coupling of aryl bromides and aryl alkynes, in air and in a non-anhydrous solvent, in high yields.

A general catalyst for Suzuki-Miyaura and Sonogashira reactions of aryl and heteroaryl chlorides in water

We report the synthesis of 2-(3-sulfonatomesityl)-5-sulfonatoindenyl) dicyclohexylphosphine hydrate sodium salt and its use in palladium-catalyzed Suzuki-Miyaura and Sonogashira coupling reactions in water (and biphasic water-organic solvent mixtures) to prepare a variety of functionalized biaryls and aryl alkynes in excellent yield. This journal is the Partner Organisations 2014.

Palladium-poly(3-aminoquinoline) hollow-sphere composite: Application in sonogashira coupling reactions

We report on the use of palladium acetate for the synthesis of a palladium-based polymer composite material as a catalyst for Sonogashira cross-coupling reactions for aryl and heteroaryl of iodides and bromides.

Synthesis of unsymmetrically disubstituted ethynes by the palladium/copper(I)-cocatalyzed sila-Sonogashira-Hagihara coupling reactions of alkynylsilanes with aryl iodides, bromides, and chlorides through a direct activation of a carbon-silicon bond

In this paper, we explore the copper/palladium-cocatalyzed cross-coupling reactions of 1-aryl-2-trimethylsilylethynes with aryl iodides, bromides, and chlorides as coupling partners, to furnish unsymmetrically disubstituted ethynes in moderate to excellent yields. Various aryl iodides were subjected to reaction under the optimized conditions with 5 mol % of Pd(PPh3) 2 and 50 mol % of CuCl. The steric properties of the aryl iodide proved more influential to the outcome of the cross-coupling reaction than electronic factors. In addition, we succeeded in synthesizing unsymmetrical diarylethynes using two different aryl iodides in one-pot. Furthermore, under the same reaction conditions with 10 mol % of PdCl2, 40 mol % of P(4-FC6H4)3, and 50 mol % of CuCl as catalyst, we succeeded in synthesizing unsymmetrical diarylethynes from various aryl bromides. Finally, we explored reactions with aryl chlorides and duly discovered that unsymmetrical diarylethynes were obtainable in moderate to good yields when 10 mol % of Pd(OAc)2, 10 mol % of (-)-DIOP, and 10 mol % of CuCl were used. These reactions proceed through a direct activation of a carbon-silicon bond in alkynylsilanes by CuCl to generate the corresponding alkynylcopper species via transmetalation from silicon to copper. Mechanistic investigations on the reaction of alkynylsilanes with aryl bromides confirmed that the trimethylsilyl bromide generated in situ retarded both transmetalation steps between CuCl and alkynylsilane, and between palladium(II) species formed by oxidative addition and alkynylcopper species.