22557-06-8

Upstream product

• 100-39-0 benzyl bromide 
• 16520-62-0 4-Phenyl-1-butyne 
• 103-64-0 bromostyrene 
• 3031-68-3 Hexa-2,4-diyne-1,6-diol 
• 16260-59-6 1,6-dichlorohexa-2,4-diyne 
• 6921-34-2 benzylmagnesium chloride 

Downstream Products

• 1092074-94-6 (Z)-1,8-diphenyloct-3-en-5-yne 
• 1092075-02-9 (E)-2-phenethyl-1,7-diphenylhept-2-en-4-yn-1-ol 

Relevant academic research and scientific papers

Homocoupling of terminal alkynes catalysed by ultrafine copper nanoparticles on titania

Copper nanoparticles on titania effectively catalyse the oxidative homocoupling of terminal alkynes in the presence of piperidine as a base in tetrahydrofuran (THF) or under solvent-free conditions. A wide range of diynes have been synthesised in high yie

Transmetalation of palladium enolate and its application in palladium-catalyzed homocoupling of alkynes: A room-temperature, highly efficient route to make diynes

A novel pathway for the homocoupling reaction has been achieved using a similar protocol as the cross-coupling reaction. Ethyl bromoacetate is chosen to initiate the coupling reaction through oxidatlve addition to a Pd(0) species, and an PdBr(enolate) intermediate is formed. This intermediate can undergo double transmetalation with an alkynyl copper reagent, and reductive elimination produces a variety of diynes in high yields.

Stereoselective Synthesis of Highly Substituted Conjugated Dienes via Pd-Catalyzed Carbonylation of 1,3-Diynes

The stereoselective synthesis of conjugated dienes was realized for the first time via Pd-catalyzed alkoxycarbonylation of easily available 1,3-diynes. Key to success is the utilization of the specific ligand 1,1′-ferrocenediyl-bis(tert-butyl(pyridin-2-yl)phosphine) (L1), which allows this novel transformation to proceed at room temperature. A range of 1,2,3,4-tetrasubstituted conjugated dienes are obtained in this straightforward access in high yields and selectivities. The synthetic utility of the protocol is showcased in the concise synthesis of several important intermediates for construction of natural products rac-cagayanin, rac-galbulin, rac-agastinol, and cannabisin G.

Copper(I)-catalyzed stereoselective hydrogenation of 1,3-diynes and enynes

A stereoselective hydrogenation of 1,3-diynes with an air-stable copper(I)/N-heterocyclic carbene complex, [IPrCuOH], has been developed. The corresponding products, 1,3-dienes, are obtained in a stereoselective manner depending on their substitution pattern: Diaryl-diynes yield E,E-1,3-dienes, whereas dialkyl-diynes are converted to the corresponding Z,Z-1,3-dienes. Hydrogenation and deuteration experiments with enynes indicate that these are competent reaction intermediates in the hydrogenation of diynes.

Synthesis of ene-yne-enes by nickel-catalyzed double SN2′ substitution of 1,6-dichlorohexa-2,4-diyne

1,6-Dichlorohexa-2,4-diyne undergoes nickel-catalyzed double substitution with aryl and alkenyl Grignard reagents to provide substituted ene-yne-enes. The reaction is formally an extension of the well-described SN2′-allylic and -propargylic substitution reactions but the mechanism is considerably more complex. The products might function as building blocks for conjugated polymers.

Cu(ii) complex heterogenized on SBA-15: A highly efficient and additive-free solid catalyst for the homocoupling of alkynes

A Cu(ii) complex has been heterogenized on SBA-15 by functionalization of SBA-15 with (N1-propylethane-1,2-diamine) triethoxysilane (NN-SBA-15) followed by anchoring of 2-pyridinecarboxaldehyde through Schiff's base formation between the terminal -NH

ICl-mediated intramolecular twofold iodoarylation of diynes and diynyl diethers and amines: Synthesis of bis(2 H-hydronaphthalene and chromene) and 2H-quinoline bearing an alkenyl iodide moiety

Electrophilic intramolecular twofold iodoarylation was developed from the reaction of diynes and diynyl diethers and amines with iodine monochloride under mild conditions, which produced bis(2H-hydronaphthalene and chromene) and 2H-quinoline bearing an al

Copper nanoparticles supported on silica coated maghemite as versatile, magnetically recoverable and reusable catalyst for alkyne coupling and cycloaddition reactions

A versatile and magnetically recoverable catalyst consisting of copper nanoparticles on silica coated maghemite nanoparticles (MagSilica ) is presented. The catalyst has been prepared under mild conditions by fast reduction of anhydrous CuClsu

Ligand-accelerating low-loading copper-catalyzed effective synthesis of (E)-1,3-enynes by coupling between vinyl halides and alkynes performed in water

The useful conjugated enynes could be easily prepared via low-loading (0.0001 mol %) copper-catalyzed coupling between vinyl halides and terminal alkynes. It is noteworthy that this reaction could be preformed in water without using any co-solvents and the desired 1,3-enynes could be obtained with good yields. In the catalytic reaction, ligand-acceleration effect was markable.

Organic reaction in Solkane 365 mfc: Homocoupling reaction of terminal alkynes

Solkane 365 mfc is proven to be an environmentally benign alternative solvent for the homocoupling reaction of terminal alkynes catalyzed by CuCl/TMEDA under air at room temperature. A variety of terminal alkynes, including aromatic, heteroaromatic and aliphatic alkynes, were cleanly transformed into 1,3-diynes within a short period in high to excellent yields up to 98%. The Royal Society of Chemistry.