69374-83-0

Upstream product

• 79887-09-5 (4-butylphenyl)acetylene 
• 41492-05-1 p-bromobutylbenzene 
• 20651-67-6 4-butyliodobenzene 
• 75-20-7 calcium carbide 

Downstream Products

• 183210-97-1 (Z,Z)-1,4-di(benzylthio)-1,4-di(p-n-butylphenyl)-1,3-butadiene 
• 1411910-03-6 8-butyl-6-(4-butylphenyl)-1,3-dimethylbenzo[f]quinazoline 
• 183211-23-6 3,6-Bis-(4-butyl-phenyl)-[1,2]dithiine 

Relevant academic research and scientific papers

Synthesis of 1,3-Diynes Using Calcium Carbide as an Alkyne Source

A simple method for the synthesis of 1,3-diynes from iodoarenes using calcium carbide as an alkyne source and air as an oxidant is described. A series of 1,4-diarylbuta-1,3-diynes were efficiently synthesized by this strategy. The salient features of this protocol are the use of inexpensive and easy-to-handle alkyne source, broad substrate scope, open-air condition, and simple operation procedure.

Leaf-like CuO nanosheets on rGO as an efficient heterogeneous catalyst for Csp-Csp homocoupling of terminal alkynes

In this work, the economic and well-defined leaf-like CuO nanosheets on rGO (CuO nanosheets/rGO) was synthesized by a convenient hydrothermal method. The morphology and chemical composition of CuO nanosheets/rGO were confirmed by XRD, SEM-EDS, TEM, HR-TEM, and XPS techniques. The CuO nanosheets/rGO was successfully applied as a high-performance heterogeneous catalyst in the homocoupling of 12 terminal alkynes, and the isolated yield of each product was more than 80%, except for propargyl alcohol. This catalyst could be reused five times with little activity loss. Thus, it is beneficial for green and sustainable development of organic synthetic chemistry.

Reaction Selectivity in On-Surface Chemistry by Surface Coverage Control—Alkyne Dimerization versus Alkyne Trimerization

This work reports the influence of molecular coverage in on-surface C?C-bond formation on reaction outcome. 6-Ethynyl-2-naphthoic acid (ENA) was chosen as organic component and Ag(111) as substrate. The alkyne moiety in ENA can either react by dimerizatio

Efficient P, O chelate palladium(II)/AgNO3cocatalyzed homocoupling of aromatic terminal alkynes in aqueous media under ambient atmosphere

A new and efficient protocol for the P, O chelate Pd(II)/AgNO3cocatalyzed oxidative homocoupling reaction of aromatic terminal alkynes in the synthesis of symmetrical 1,4-disubstituted-1,3-diynes was described in aqueous media under ambient atmosphere. The results showed that both NEt3and THF/H2O (in 4:1 proportion) played crucial roles in the reaction. In contrast, this protocol employs a low palladium(II) complex loading and AgNO3as cocatalyst to obtain the homocoupled products in moderate to good yields.

Magnetic copper ferrite catalyzed homo- and cross-coupling reaction of terminal alkynes under ambient atmosphere

The application of non-toxic and magnetically separable nano-CuFe2O4 as an efficient catalyst for oxidative homo- and cross-coupling reaction of terminal alkynes is described. A wide range of symmetrical and unsymmetrical 1,3-diynes have been synthesized in moderate to good yields under ambient atmosphere. The nano CuFe2O4 can be recovered with a magnet and reused at least five consecutive cycles with no appreciable loss of its catalytic activity.

The Choice Is Yours: Using Liquid-Assisted Grinding to Choose between Products in the Palladium-Catalyzed Dimerization of Terminal Alkynes

Herein, we report on the dimerization of terminal alkynes using various palladium catalysts under solvent-free mechanochemical conditions. When tetrakis(triphenylphosphine)palladium(0) was employed as the catalyst, we observed the 1,3-butadiyne as the major product. However, when we employed bis(triphenylphosphine)palladium(II) dichloride as the catalyst, we observed the trans-enyne as the major product. When we used a polymer-supported bis(triphenylphosphine)palladium(II) dichloride catalyst under liquid-assisted grinding conditions, we discovered the ability to tune the catalyst to generate either the diyne or trans-enyne as the major product, depending on the grinding medium.

Application of the polyacrylonitrile fiber as a novel support for polymer-supported copper catalysts in terminal alkyne homocoupling reactions

A commercially available synthetic polyacrylonitrile fiber, capable of acting as a novel support for polymer-supported copper catalyst in terminal alkyne homocoupling reactions, is presented. Detailed characterization by inductively coupled plasma (ICP) analysis, Fourier transform infrared spectroscopy (FTIR), and scanning electron microscopy (SEM) confirmed the changes and stability of the fiber catalyst during the modification and utilization processes. Moreover, the catalytic reactions proceeded at room temperature using air as a green oxidant to afford nearly quantitative yields (95-99%); the fiber catalyst has shown excellent activity and superior recyclability (over 16 cycles); and the procedure is operationally simple and amenable to the gram scale in continuous-flow processing. Furthermore, the prominent features (high strength, good flexibility, etc.) of the polyacrylonitrile fiber make the fiber-supported catalyst very attractive for fixed-bed reactors in the chemical industry.

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

Copper(i) chloride catalysed room temperature Csp-Csp homocoupling of terminal alkynes mediated by visible light

We developed a technique mediated by visible light for the aerobic homocoupling of terminal alkynes to synthesize 1,3-conjugated diynes using a copper(i) chloride catalyst at room temperature. Compared with previously reported thermal processes, this photochemical method is simple, uses only mild reaction conditions, produces high yields and works well for substrates with electron-withdrawing groups without the need for bases/ligands, oxidants or palladium catalysts.

Copper porphyrin-catalyzed aerobic oxidative coupling of terminal alkynes with high TON

Copper porphyrin-catalyzed Glaser-Hay-type couplings of terminal alkynes generating 1,3-diynes are described. This reaction features high TON (up to 950) and is complete in an hour, providing a facile, clean, and efficient protocol to access various 1,3-d