136053-56-0

Upstream product

• 766-47-2 1-ethynyl-2-methylbenzene 
• 615-37-2 ortho-methylphenyl iodide 
• 471-25-0 Propiolic acid 
• 3989-15-9 trimethyl[(2-methylphenyl)ethynyl]silane 
• 187329-19-7 C₉H₇BrMg 
• 1620057-23-9 bis(2-methoxyphenyl)(phenyl)(o-tolylethynyl)phosphonium bromide 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 104464-03-1 1,1-dibromo-2-(2-methylphenyl)ethene 
• 529-20-4 2-methylphenyl aldehyde 
• 7515-27-7 3-(2-methylphenyl)prop-2-ynoic acid 

Downstream Products

• 1276043-72-1 (Z)-benzyl(1,4-di-o-tolylbut-1-en-3-ynyl)selane 
• 1374219-60-9 5-(2-methylbenzyl)-3-(o-tolyl)isoxazole 

Relevant academic research and scientific papers

First report of a nano-Cu2O-catalyzed protocol for homo-coupling reaction of terminal alkynes in water/ionic liquid medium

A new, efficient and green protocol for the nano-Cu2O-catalyzed homo-coupling reaction of terminal alkynes has been developed, using water/ionic liquid as an environmentally friendly solvent. Moreover, the system also allows the synthesis of unsymmetric 1,3-diynes by cross-coupling of two different terminal alkynes. It is noteworthy that the nano-Cu2O-catalyzed methodology is a good supplement to copper catalyst for the Glaser-type homo-coupling reaction. Copyright

Synthesis of symmetrical 1,3-butadiynes by homocoupling reactions of alkynylboronates mediated by a copper salt

Alkynylboronates are employed as a practical and versatile precursor for a variety of π-conjugated organic compounds. In the presence of a Cu(I) or Cu(II) salt, transformation of alkynylboronates into the corresponding 1,3-diynes upon exposure to air takes place readily in aprotic polar solvents such as DMI.

Silver-catalyzed Glaser coupling of alkynes

Excellent yields were obtained from the silver nitrate-catalyzed homocoupling reaction of alkynes in N,N-dimethylformamide using triphenylphosphine as ligand. This safe and simple silver catalytic system has been employed in a safe and efficient protocol

Homocoupling reaction of terminal alkynes catalyzed by a reusable cationic 2,2′-bipyridyl palladium(II)/CuI system in water

A cationic 2,2′-bipyridyl palladium(II)/CuI system was proven to be a reusable and highly efficient catalyst for the homocoupling of terminal alkynes at room temperature using water as a solvent in the presence of TBAB under aerobic conditions. For aromatic terminal alkynes, the reaction was performed either with or without I2 as an oxidant; the addition of I 2 was required when aliphatic terminal alkynes were used as a substrate for the homocoupling reaction. In the presence of 0.0001-1 mol% palladium catalyst and 1 mol% CuI, a variety of terminal alkynes were homocoupled in good to excellent yields. The water-soluble catalytic system was separated from the organic products by extraction and the residual aqueous solution showed activity for reuse for several cycles without a significant decrease in activity.

One-pot synthesis of 1,4-diarylsubstituted 1,3-diynes from the sequential coupling reactions of aryl iodides and propiolic acid

1,4-Disubstituted 1,3-dialkynes were obtained from the one-pot palladium/copper-catalyzed coupling reactions of aryl iodide and propiolic acid. The optimized catalytic system consisted of 5.0 mol % Pd(PPh3) 2Cl2, 10 mol % dppb, 10 mol % CuI, 2.4 equiv of DBU, and 1.2 equiv of K2CO3. The coupling reaction was carried out at 30 °C for 6 h and subsequently at 80 °C for 3 h.

Recyclable Polystyrene-Supported Copper Catalysts for the Aerobic Oxidative Homocoupling of Terminal Alkynes

Polystyrene-supported copper(II) N,N,N′,N′-tetraethyldiethylenetriamine [Cu(II)-TEDETA] complexes were prepared by immobilization of TEDETA onto crosslinked polystyrene resin, followed by complexation with copper salts. The polystyrene-immobilized CuSOsu

Heterogeneously catalyzed efficient alkyne-alkyne homocoupling by supported copper hydroxide on titanium oxide

The role of the supported Copper Hydroxide on Titanium Oxide as an efficient heterogeneous catalyst for the oxidative alkyne-alkyne homocoupling was analyzed. The catalytic activities for the homocoupling of ethynylbenzene to 1,4-diphenyl-1,3-butadiyne were compared with various catalysts in toluene under oxygen atmosphere. No homocoupling reaction proceeded with bulk copper oxides and hydroxide. The inductively coupled plasma atomic emission spectroscopy analysis revealed that no copper species was found in the filtrate. Therefore, the role of the copper hydroxide species is probably the abstraction of an alkyne hydrogen to form the alkynyl species. The supported copper hydroxide could act as an efficient heterogenous catalyst for the oxidative alkyne-alkyne homocoupling.

Palladium-Catalyzed Aerobic Homocoupling of Alkynes: Full Mechanistic Characterization of a More Complex Oxidase-Type Behavior

A combined experimental and computational approach has been used to shed light on the mechanism of the Pd-catalyzed oxidative homocoupling of alkynes using oxygen as the oxidant. Mechanistic understanding is important because of the synthetically relevant direct involvement of oxygen in the oxidative coupling and because of the presence of related processes as undesired side reactions in cross-coupling reactions involving terminal alkynes. A low-ligated [Pd(PPh3)(alkyne)] complex is key in the process, and it can be conveniently generated from allylic palladium(II) complexes in the presence of a base or from Pd(I) allylic dimers as precatalysts. The catalytic coupling occurs by alkyne metalation to give an anionic [Pd(PPh3)(alkynyl)]- complex that is then oxidized by oxygen. The interaction with oxygen occurs only on this electron-rich Pd(0) anionic species and leads to a (κO,κO-peroxo)palladium(II) singlet intermediate that undergoes subsequent protonolysis to give a (κO-hydroperoxo)palladium(II) complex and then hydrogen peroxide. The second alkyne metalation occurs on a Pd(II) derivative to give a bis(alkynyl)palladium(II) complex that evolves to the product by reductive elimination as the product-forming step. This reaction is an oxidase-type process that, in contrast to most Pd-catalyzed oxidative processes, occurs without separation of the substrate transformation and the catalyst oxidation, with these two processes being intertwined and dependent on one another.

Copper(i)-catalyzed homo-coupling of terminal alkynes at room temperature under solvent and base free conditions using O2 as an oxidant

The homo-coupling of various terminal alkynes were realized in the presence of 0.5 mol% CuI and 5 mol% benzylamine. This transformation proceeded at room temperature under solvent and base free conditions using O2 as an oxidant. The TON was up to 1760.

Efficient alkyne homocoupling catalysed by copper immobilized on functionalized silica

Copper immobilized on a functionalized silica support is a good catalyst for the homocoupling of terminal alkynes. The so-called Glaser-Hay coupling reaction can be run in air with catalytic amounts of base. The copper catalyst is active for multiple subs