62158-75-2

Upstream product

• 931-48-6 2-cyclohexylacetylene 
• 60754-49-6 1,1-dibromo-2-cyclohexylethene 
• 123325-10-0 (cyclohexylethynyl)magnesium bromide 
• 583-55-1 1-Bromo-2-iodobenzene 
• 1430234-71-1 1,5-dicyclohexylpenta-1,4-diyn-3-ol 
• 1430234-45-9 1,5-dicyclohexylpenta-1,4-diyn-3-one 
• 42134-54-3 3-cyclohexyl-2-propyn-1-ol 
• 536-74-3 phenylacetylene 
• 50284-86-1 1-chloro-2-cyclohexylethyne 
• 81602-60-0 1,2-dibromo-1-cyclohexylethane 
• 695-12-5 vinylcyclohexane 
• 97537-57-0 cyclohexylethynyl-trimethyl-stannane 

Downstream Products

• 1374219-45-0 3-cyclohexyl-5-(cyclohexylmethyl)isoxazole 
• 1422144-13-5 3-cyclohexyl-5-(cyclohexylmethyl)-1H-pyrazole 
• 62158-74-1 (E)-1,4-dicyclohexyl-1-buten-3-yne 
• 16636-32-1 cis,cis-Dicyclohexyl-buta-1,3-dien 

Relevant academic research and scientific papers

1-Alkynyl(aryl)(tetrafluoroborato)-λ3-bromanes as highly efficient Michael acceptors: Uncatalyzed conjugate addition of 1-alkynyl(trialkyl)stannanes to yield symmetrical and unsymmetrical 1,3-butadiynes

(Equation Presented) Symmetrical 1,3-diynes result from the oxidative homocoupling reaction of alkynylstannanes with an aryldifluoro- λ3-bromane in the presence of BF3·Et 2O (see scheme, Ar = p-CF3C6H4). The reaction involves a Michael addition of alkynylstannanes to the initially formed alkynyl-λ3-bromanes. Cross-coupling of alkynyl-λ3-bromanes with alkynylstannanes affords unsymmetrical 1,3-diynes (see scheme).

Method for preparing conjugated diyne compound by using copper complex

The invention relates to a method for preparing a conjugated diyne compound by using a copper complex. The method comprises the following step of: in the presence of alkali, carrying out a Glaser coupling reaction at room temperature by using alkyne as a raw material, the copper complex containing ortho-carborane Schiff base ligand as a catalyst and air as an oxidizing agent to prepare the conjugated diyne compound. Compared with the prior art, the copper complex containing the ortho-carborane Schiff base ligand is used for efficiently catalyzing the Glaser coupling reaction of alkyne to prepare the conjugated diyne compound; and the method has the advantages that selectivity is good, a catalyst dosage is low, reaction conditions are mild, a reaction can be performed in an open manner (wherein air is used as an oxidizing agent), a reaction rate is high, yield is relatively high, a substrate range is wide, and the method has wide application prospects in industry.

Reduced graphene oxide supported copper oxide nanocomposites: An efficient heterogeneous and reusable catalyst for the synthesis of ynones, 1,3-diynes and 1,5-benzodiazepines in one-pot under sustainable reaction conditions

A greener and efficient method for the synthesis of ynones and 1,3-diynes using copper oxide nanoparticles (CuONPs) doped reduced graphene oxide (CuO@rGO) catalyst under palladium, ligand and solvent free conditions have been developed. The catalyst was s

Study of the versatility of CuBTC?IL-derived materials for heterogeneous catalysis

The versatility of CuBTC (or HKUST-1) MOF materials to be functionalized to tune their catalytic activity performance was evaluated. The MOFs were functionalized with ionic liquids (ILs) to give rise to catalysts able to adsorb CO2and react with epoxides to produce carbonates. The materials are active for this reaction and show good conversion rates at 100 °C and 7 bar CO2, confirming their ability to fix this gas and transform it into valuable products. In addition, the MOF?IL composite material1can be functionalized to give rise to a bimetallic catalyst, taking advantage of the N-heterocyclic carbene present in the imidazolium-based ILs. Therefore, the material was reacted with palladium dichloride, yielding CuBTC?IL-(NHC)Pd (1Pd) which has been tested for homocoupling of alkynes and imination of benzyl alcohol reactions. The recyclability of the catalysts has been studied and hot filtration tests have been made.

Ruthenium-Catalyzed trans-Hydroalkynylation and trans-Chloroalkynylation of Internal Alkynes

[Cp*RuCl]4 catalyzes the addition of iPr3SiCCX (X = H, Cl) across internal alkynes with formation of 1,3-enyne or 1-chloro-1,3-enyne derivatives, respectively; the reaction follows an unorthodox trans-addition mode. The well-balanced affinities of the different reaction partners to the ruthenium catalyst ensure that crossed addition prevails over homodimerization of the individual components, as can be deduced from spectroscopic and crystallographic data of various intermediates; this includes a dinuclear complex in which an internal alkyne bridges two [Cp*RuCl] fragments.

Copper Nanoparticles on Ordered Mesoporous Carbon Nitride Support: a Superior Catalyst for Homo- and Cross-Coupling of Terminal Alkynes under Base-Free Conditions

A novel ordered mesoporous carbon nitride (OMCN) was synthesized as a functionalized support with 2,4,6-trichloro-1,3,5-triazine and benzidine as starting materials in the presence of SBA-15 as a template. Copper nanoparticles were then loaded on the C–N material to achieve a novel nanocomposite catalyst (Cu NPs-OMCN). The nanocomposite was utilized as a highly efficient catalyst for homo- and cross-coupling of terminal alkynes under base-free conditions in ethanol, and various symmetrical and unsymmetrical 1,3-diynes were obtained with good to excellent yields. Moreover, based on this reaction, a one-pot approach to synthesize 2,5-disubstituted thiophenes and furans from terminal alkynes were developed. Furthermore, the heterogeneous catalyst could be recovered and reused conveniently for several times with satisfactory 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.

Recyclable Cu/C3N4 composite catalysed homo- and cross-coupling of terminal alkynes under mild conditions

A Cu/C3N4 composite was prepared and utilized as a highly efficient and environmentally friendly catalyst for the homo- & cross-coupling of terminal alkynes. Excellent functional group tolerance and good yields were observed with oxygen as an oxidant in an isopropanol solution (or as additive) under ambient conditions. Furthermore, the composite catalyst shows good recyclability and can be recovered simply and reused several times without significant loss in its catalytic activities.

Continuous-flow oxidative homocouplings without auxiliary substances: Exploiting a solid base catalyst

The catalytic oxidative dimerization of aromatic amines and acetylenes is of outstanding synthetic importance among homocoupling reactions. Both transformations necessitate the use of extraneous bases and ligands, which contains significant disadvantages as concerns environmental impacts and process costs. We exploited the inherent basic character of a copper-containing layered double hydroxide to facilitate the catalytic homocouplings of alkynes and aniline derivatives without the need for any auxiliary substances. The reactions were studied in a continuous-flow system to achieve extended parameter spaces for chemical intensification, and also to avoid undesired reaction pathways by means of strategic control over the residence time. Valuable 1,4-disubstituted 1,3-diynes and diversely substituted aromatic azo compounds were achieved chemoselectively in excellent yields and in short process times even on preparative scales.

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.