889-42-9

Upstream product

• 5075-59-2 diethyl(phenylethynyl)aluminum 
• 934-94-1 1-bromo-4-bromoethynyl-benzene 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 6738-06-3 phenylethynylmagnesium bromide 
• 2579-22-8 Phenylpropargyl aldehyde 
• 91110-68-8 1-bromo-4-((phenylsulfonyl)methyl)benzene 
• 536-74-3 phenylacetylene 
• 63704-44-9 potassium 3-phenylpropiolate 
• 136350-66-8 1-bromo-4-(2,2-dibromovinyl)benzene 
• 1430234-94-8 1-(4-bromophenyl)-5-phenylpenta-1,4-diyn-3-one 
• 591-50-4 iodobenzene 
• 861718-54-9 (Ph₃P)AuCCCCAu(PPh₃) 
• 589-87-7 1,4-bromoiodobenzene 

Downstream Products

• 13667-10-2 Diphenyl-[4-(4-phenyl-buta-1,3-diynyl)-phenyl]-methanol 

Relevant academic research and scientific papers

Copper (II) catalyzed homocoupling and heterocoupling of terminal alkynes

Cu(OTf)2 catalyzed homo– and heterocoupling of aromatic and aliphatic terminal alkynes has been developed. Symmetric and unsymmetric 1,3-diynes have been synthesized in good yields under an aerobic condition in the presence of an organic base D

An efficient heterogeneous palladium(0)-catalysed cross-coupling between 1-bromoalkynes and terminal alkynes leading to unsymmetrical 1,3-diynes

An efficient heterogeneous palladium(0)-catalysed cross-coupling of 1-bromoalkynes with terminal alkynes was achieved in DMF at room temperature in the presence of 5 mol% of MCM-41-immobilised bidentate phosphine palladium(0) complex [MCM-41-2P-Pd(0)] and 2 mol% of CuI with Et3N as base, yielding a variety of unsymmetrical 1,3-diynes in moderate to good yields. This heterogeneous palladium(0) complex could be easily recovered by a simple filtration of the reaction solution and recycled at least seven times without significant decrease in activity.

Transition metal-free coupling of terminal alkynes and hypervalent iodine-based alkyne-transfer reagents to access unsymmetrical 1,3-diynes

A variety of unsymmetrical 1,3-diynes can easily be accessed in good yields under catalyst- and transition metal-free conditions by reacting terminal alkynes with hypervalent iodine-based electrophilic alkyne-transfer reagents.

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.

"Anti-Michael addition" of Grignard reagents to sulfonylacetylenes: Synthesis of alkynes

In this work, the addition of Grignard reagents to arylsulfonylacetylenes, which undergoes an "anti-Michael addition", resulting in their alkynylation under very mild conditions is described. The simplicity of the experimental procedure and the functional

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.

Synthetic method of asymmetric 1,4-diarylbutadiyne compounds

The invention discloses a synthetic method of asymmetric 1,4-diarylbutadiyne compounds. A double elimination method is employed in the method; with [alpha]-methylenesulfone and alkynyl aldehyde as raw materials, a series of asymmetric 1,4-diarylbutadiyne compounds are synthesized. The synthetic method is free of heavy metals and is green and environment-friendly. Compared with cross-coupling raw material synthesis with metal acetylides and halogenated terminal alkyne, the method is simple; and compared with a homocoupling reaction of terminal alkyne, the method can be used for synthesizing asymmetric conjugate diyne.

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

Cu-catalyzed Fe-driven Csp-Csp and C sp-Csp2 cross-coupling: An access to 1,3-diynes and 1,3-enynes

An efficient Csp-Csp cross-coupling of alkynyl bromide and pinacol ester of alkynyl boronic acid catalyzed by CuFe 2O4 nanoparticles has been accomplished in dimethyl carbonate to produce unsymmetric 1,3-diynes. This protocol is also extended for the Csp-Csp2 coupling of alkynyl bromide and alkenyl boronic acid to provide conjugated 1,3-enynes. The aliphatic, aromatic, and heteroaromatic alkynes couple with various substituted alkynyl/alkenyl boronates/boronic acids by this procedure to furnish a library of 1,3-diynes and enynes in high yields. The catalyst was easily separated by an external magnet and recycled 10 times.

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.