733035-88-6

Upstream product

• 100-54-9 pyridine-3-carbonitrile 
• 766-97-2 4-n-methylphenylacetylene 
• 626-55-1 3-Bromopyridine 
• 2510-23-8 3-Ethynylpyridine 
• 5720-05-8 4-methylphenylboronic acid 
• 624-31-7 4-tolyl iodide 
• 471-25-0 Propiolic acid 
• 2227-58-9 3-(4-methylphenyl)prop-2-ynoic acid 
• 106-38-7 para-bromotoluene 
• 1120-90-7 3-iodopyridine 
• 1418305-41-5 1-(pyridin-3-yl)-3-(p-tolyl)prop-2-yn-1-one 
• 462-08-8 pyridin-3-ylamine 

Downstream Products

• 6892-33-7 3-[2-(4-methylphenyl)ethenyl]pyridine 
• 5847-66-5 3-[2-(4-methylphenyl)ethenyl]pyridine 
• 40061-31-2 1-(pyridin-3-yl)-2-p-tolyl-ethane-1,2-dione 

Relevant academic research and scientific papers

Quantitative dynamic interconversion between AgI-mediated capsule and cage complexes accompanying guest encapsulation/release

(Chemical Equation Presented) An accommodating host: Capsule- and cage-shaped complexes are formed from AgI and disk-shaped trismonodentate ligands in 1:1 and 1.5:1 concentration ratios, respectively; their interconversion is reversible. The ca

Production method of diaryl alkyne compound

The invention discloses a production method of a diaryl alkyne compound. The production method of the diaryl alkyne compound comprises the steps of under protection of nitrogen, placing a bromobenzenesubstrate, alkynol, a palladium catalyst, an organic phosphine ligand and inorganic alkali into a reaction container, then adding a solvent, heating the reaction container for reaction, after the reaction container is cooled to room temperature, adding a saturated ammonium chloride solution for quenching, and then conducting extraction and column chromatography isolation and purification to obtain the diaryl alkyne compound. According to the production method of the diaryl alkyne compound, the aryl bromide and the alkynol which are simple and easy to obtain are used as raw materials, and through the palladium-catalyzed coupling reaction, the diaryl alkyne compound is obtained. The reaction raw materials are simple and easy to obtain, reaction conditions are mild, several defects in a traditional synthesis method are overcome, for example, the defect that when calcium carbide is used as a raw material, the release speed of acetylene cannot be controlled is overcome, the defect that when terminal alkyne is used as a raw material, a product and the raw material are hard to separate due to similar polarity is overcome, and the like. The method also has good performance in amplification reaction, so that the method has great application prospects.

Using Anilines as Masked Cross-Coupling Partners: Design of a Telescoped Three-Step Flow Diazotization, Iododediazotization, Cross-Coupling Process

The conversion of commercially available anilines into biaryl and biarylacetylene products was realized by using a telescoped, three-reactor flow diazotization/iododediazotization/cross-coupling process. The segmented flow stream created by off-gassing during the Sandmeyer sequence was restored to a continuous column of reaction solution by using a specially designed continuous-flow unit controlled by custom software created in-house. The resultant aryl iodide was then combined with a stream of cross-coupling solution that fed into the final reactor. The system proved versatile as modifications to the diazotization/iododediazotization sequence could be made rapidly to account for any substrate specificity (e.g., solubility problems), leading to a wide substrate scope of Suzuki–Miyaura and Sonogashira cross-coupled products.

Synthesis, Crystal Structures, and Catalytic Application of Two Triphenylphosphine-Cyclopalladated Ferrocenylpyrazine Complexes Containing Chlorine/Iodine Anion

Two new triphenylphosphine-cyclopalladated ferrocenylpyrazine complexes containing chlorine/iodine anion 2-3 have been easily prepared from the bridge-splitting reaction of the palladacyclic dimer 1 and anion exchange reaction, respectively. They were characterized by elemental analysis, IR, and 1H NMR. Additionally, the structures of these two complexes were determined by single-crystal X-ray analysis and C-H···N hydrogen bonds and π-π interactions were found in the their crystal structures. These complexes displayed good activity in the coupling of terminal alkynes with arylboronic acids under atmospheric conditions. This method provided the corresponding arylalkynes with good to excellent yields.

Rh-catalyzed decarbonylation of conjugated ynones via carbon-alkyne bond activation: Reaction scope and mechanistic exploration via DFT calculations

In this full article, detailed development of a catalytic decarbonylation of conjugated monoynones to synthesize disubstituted alkynes is described. The reaction scope and limitation has been thoroughly investigated, and a broad range of functional groups

Dimethylaminoalkyl chalcogenolate palladium(II) complexes as an efficient copper-and phosphine-free catalyst for Sonogashira reaction

N,N-Dimethylaminoalkyl chalcogenolate Pd(II) complexes [PdCl(E a∩NMe2)]n has been investigated as a moisture/air-stable and robust catalyst for Sonogashira cross-coupling reaction in the absence of copper and phosphine ligand. The dimeric palladium(II) complex of selenium containing ligand shows the best catalytic activity as compared with monomeric and trimeric complexes. The variety of functional groups are tolerated under optimized catalytic systems and provide excellent yields of the products.

N-heterocyclic carbene adducts of cyclopalladated ferrocenylpyridine containing chloride or iodide anions: Synthesis, crystal structures and application in the coupling of terminal alkynes with arylboronic acids

Two air-stable N-heterocyclic carbene (NHC) adducts of cyclopalladated ferrocenylpyridine containing chloride or iodide anions 2-3 have been easily prepared from the bridge-splitting reaction of the palladacyclic dimer 1 and anion exchange reaction, respectively. They were characterized by elemental analysis, IR, 1H, and 13C NMR. Additionally, the structures of these complexes were determined by single-crystal X-ray analysis. These adducts have been successfully applied to the coupling of terminal alkynes with arylboronic acids under atmospheric conditions.

Phosphine-free palladium-catalyzed decarboxylative coupling of alkynylcarboxylic acids with aryl and heteroaryl halides

We herein report the design and development of a carboxyamido/carbene ligand and its Pd-complex for the decarboxylative coupling of alkynylcarboxylic acids with aryl and heteroaryl halides to afford arylalkynes. Copyright

Practical synthesis of unsymmetrical diarylacetylenes from propiolic acid and two different aryl bromides

A palladium catalyst that mediates the one-pot sequential Sonogashira and decarboxylative coupling of propiolic acid with two different aryl bromides has been developed. Selective coupling of the first aryl bromide was achieved in the presence of a copper-free, monometallic catalyst generated in situ from allylpalladium chloride dimer and SPhos with tetra-n-butylammonium fluoride as the base in an N-methyl-2-pyrrolidone/water solvent mixture. Upon addition of another aryl bromide and raising the temperature from 50 to 80°C, the intermediate arylpropiolic acid underwent decarboxylative coupling to give the corresponding diarylacetylene. Thus, the new system permits a one-pot three-component synthesis of unsymmetrical diarylacetylenes from widely available aryl bromides, rather than expensive aryl iodides, and propiolic acid, rather than (trimethylsilyl)acetylene, as an inexpensive and easy-to-handle acetylene synthon. The process is highly selective, modular, and gives access to a wide range of unsymmetrical diarylacetylenes in good yields. A palladium-catalyzed three component synthesis of diaryl acetylenes has been optimized. Several disubstituted alkynes have been prepared from two different arylbromides and propiolic acid in good yields. Copyright

Efficient synthesis of unsymmetric diarylalkynes from decarboxylative coupling in a continuous flow reaction system

Unsymmetric diaryl alkynes were synthesized from the palladium-catalyzed decarboxylative coupling of aryl halides and propiolic acid using a continuous flow reaction system. This flow chemistry system continuously gave the desired products in moderate to good yields, and produced less byproduct than was formed in the batch reaction.