51624-43-2

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 105836-22-4 trans-(2,3-dibromo-3-phenyl-2-propen-1-yl)triphenylphosphonium bromide 
• 33491-02-0 1-chloro-4-(chloroethynyl)benzene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 33491-03-1 1-(bromoethynyl)-4-chlorobenzene 
• 5075-59-2 diethyl(phenylethynyl)aluminum 
• 873-73-4 4-n-chlorophenylacetylene 
• 536-74-3 phenylacetylene 
• 1430234-50-6 1-(4-chlorophenyl)-5-phenylpenta-1,4-diyn-3-one 
• 66482-30-2 (Z)-1-bromo-2-(4-chlorophenyl)ethylene 
• 118616-07-2 ((E)-2,3-Dibromo-3-phenyl-allyl)-triphenyl-phosphonium; bromide 

Relevant academic research and scientific papers

Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: Synthesis of propargyl alcohols and α-ketoesters

The chemoselectivity of visible-light-induced coupling reactions of bromoalkynes with alcohols can be controlled by simple changes to the reaction atmosphere (N2 or O2). A N2 atmosphere favours propargyl alcohols via a direct C-C coupling process, whereas an O2 atmosphere results in the generation of α-ketoesters through the oxidative CC/C-O coupling pathway.

Synthesis method of asymmetric conjugated diyne

The invention provides a synthesis method of asymmetric conjugated diyne. The synthesis method comprises the following steps of A, mixing a catalyst with phenanthroline and a strong base, then adding cis-alkenyl bromide, terminal alkyne and a solvent in an argon atmosphere, and agitating, refluxing and making an obtained mixture react for 20h to 24h under a condition of 140 to 150 DEG C; B, extracting, drying and concentrating a product, and then separating and purifying the product through column chromatography, so that the asymmetric conjugated diyne is obtained. Compared with the prior art, the synthesis method provided by the invention is low in cost, easy in the obtaining of raw materials, relatively convenient to operate, high in efficiency, wide in serviceable range and suitable for the reaction of multiple substrates; further, the catalyst can be recycled.

Highly efficient synthesis of unsymmetrical 1,3-diynes from organoalane reagents and alkynyl bromides mediated by a nickel catalyst

Highly efficient and simple cross-coupling reactions of alkynylbromides with organoalane reagents for the synthesis of unsymmetrical 1,3-diynes derivatives using Ni(OAc)2 (2-5 mol%)/(o-furyl)3P (4-10 mol%) as a catalyst are reported. Excellent yields (up to 94%) were obtained for a wide range of substrates at rt or 60 °C for 2-3 h in Et2O or toluene.

Gold-Catalyzed Cadiot–Chodkiewicz-type Cross-Coupling of Terminal Alkynes with Alkynyl Hypervalent Iodine Reagents: Highly Selective Synthesis of Unsymmetrical 1,3-Diynes

A new and efficient method for the synthesis of unsymmetrical 1,3-butadiynes by gold-catalyzed C(sp)–C(sp) cross-coupling of terminal alkynes with alkynyl hypervalent iodine(III) reagents has been developed. The reaction features high selectivity and efficiency, mild reaction conditions, wide substrate scope, and functional-group compatibility, and is a highly attractive complement to existing methods. Mechanistic studies reveal that formation of a phenanthrolinyl-ligated gold(I) complex is crucial for the efficiency and selectivity of the target transformation.

Visible-light-activated copper(i) catalyzed oxidative Csp-Csp cross-coupling reaction: Efficient synthesis of unsymmetrical conjugated diynes without ligands and base

A novel visible-light-promoted copper-catalysed process for the Csp-Csp cross-coupling reaction of terminal alkynes at room temperature is described. The current photochemical method is simple, highly functional group compatible, and more viable towards the construction of bio-active 1,3-unsymmetrical conjugated diynes without the need of bases/ligands, additives and expensive palladium/gold catalysts.

Copper-catalyzed homo- and cross-coupling reactions of terminal alkynes in ethyl lactate

The bio-based chemical ethyl lactate (EL) has been discovered to be an excellent medium for the Glaser-type homo- and cross-coupling reactions of terminal alkynes. Good to excellent yields of conjugate diynes have been obtained under ligand-free and mild

Rh(I)-catalyzed decarbonylation of diynones via C-C activation: Orthogonal synthesis of conjugated diynes

Utilization of C-C bond activation as a unique mode of reactivity for constructing C-C bonds provides new strategies for preparing important organic molecules. Development of a Rh(I)-catalyzed C-C activation of diynones to synthesize symmetrical and unsymmetrical conjugated diynes through decarbonylation is reported. This C-C cleavage strategy takes advantage of the innate reactivity of conjugated ynones without relying on any ring strain or auxiliary directing group. This alkynation method also has orthogonal properties compared to typical cross-coupling reactions.

Copper(I) hydroxyapatite catalyzed sonogashira reaction of alkynes with styrenyl bromides. Reaction of cis -styrenyl bromides forming unsymmetric diynes

An efficient Sonogashira coupling of terminal alkynes and styrenyl bromides has been achieved under the catalysis of hydroxyapatite-supported copper(I). The trans-styrenyl bromides produce the usual trans-enyne products, whereas the cis-styrenyl bromides lead to unsymmetric 1,3-diynes by the cross coupling of terminal alkyne and the alkyne generated from the cis-styrenyl bromide. A series of trans-enynes and unsymmetric 1,3-diynes have been synthesized by this protocol.

Coupling reactions of alkynylsilanes mediated by a Cu(I) salt: Novel syntheses of conjugate diynes and disubstituted ethynes

Reaction of 1-trimethylsilylalkyne with copper(I) chloride in a polar solvent, DMF, at 60 °C under an aerobic conditions smoothly undergoes homo- coupling to give the corresponding symmetrical 1,3-butadiynes in 70-99% yields. In addition, (arylethynyl)trimethylsilanes are found to couple with aryl triflates and chlorides in the presence of Cu(I)/Pd(0) (10 mol %/5 or 10 mol %) cocatalyst system to give the corresponding diarylethynes in 49-99% yields. The cross-coupling reaction is applied to a one-pot synthesis of the corresponding unsymmetrical diarylethynes from (trimethylsilyl)ethyne via sequential Sonogashira-Hagihara and the present cross-coupling reactions using two different aryl triflates. The reactions of (arylethynyl)trimethylsilanes with aryl(chloro)ethynes in the presence of 10 mol % of CuCl also yield the corresponding unsymmetrical 1,3-butadiynes in 43-97% yields.

Copper(I)-catalyzed cross-coupling reaction of Alkynylsilanes with 1- chloroalkynes

A variety of unsymmetrical 1,4-biaryl-1,3-butadiyne derivatives are synthesized by a copper(I)-catalized cross-coupling reaction of alkynylsilanes with 1-chloroalkynes in moderate to good yields. These reactions are derived from the transmetalation of an alkynyl group from silicon to copper in a polar solvent.