117635-51-5

Upstream product

• 33491-05-3 1-(2-bromoethynyl)-4-methylbenzene 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 766-97-2 4-n-methylphenylacetylene 
• 1403815-27-9 C₁₃H₁₆Se 
• 2227-58-9 3-(4-methylphenyl)prop-2-ynoic acid 
• 2063-19-6 4-bromo-2-methylbut-3-yn-2-ol 

Downstream Products

• 117635-48-0 2-(p-tolylbuta-1,3-diyn-1-yl)pyridine 
• 1342819-69-5 2,2-dimethyl-5-(4-methylbenzyl)furan-3(2H)-one 
• 1342819-91-3 2,2-dimethyl-5-(4-methylbenzoyl)furan-3(2H)-one 
• 38177-85-4 1-(buta-1,3-diyn-1-yl)-4-methylbenzene 
• 16939-04-1 2-p-tolylthiophene 

Relevant academic research and scientific papers

Ni/Cu-Catalyzed Decarboxylative Addition of Alkynoic Acids to Terminal Alkynes for the Synthesis of gem-1,3-Enynes

The synthesis of gem-1,3-enynes via Ni/Cu-catalyzed decarboxylative addition of alkynoic acids to terminal alkynes has been developed. It was found that the decarboxylation of an alkynoic acid led predominantly to gem-1,3-enynes instead of 1,3-diynes, whi

Application of organoselenides in the Suzuki, Negishi, Sonogashira and Kumada cross-coupling reactions

We reported herein the regio- and stereoselective palladium-catalyzed cross-coupling reactions of unsaturated organoselenides with Sonogashira, Suzuki, Negishi and Kumada partners. The reactions were in general carried out with Pd(PPh3)4 (10 mol%), in DMF at 80 °C to afford the cross-coupling products in good yields. This strategy tolerated a wide range of substrates, such as alkynyl, vinyl, aryl and heteroaryl selenides with a variety of sensitive functional groups and gave the cross-coupling products in good yields.

Copper-catalyzed cross-coupling reactions of bromoalkynols with terminal alkynes in supercritical carbon dioxide

Copper-catalyzed cross-coupling reactions of bromoalkynols and terminal alkynes were carried out in supercritical carbon dioxide (scCO2) to afford the corresponding unsymmetrical diynes with good yields. The reaction is sensitive to temperature and the pressure of CO2. Methanol, as a cosolvent of scCO2, could promote dissolution of the inorganic salt and thus facilitated the reaction. This new heterocoupling reaction system is more environmentally friendly than more traditional methods, since it uses scCO2 as solvent and sodium acetate as base instead of amines. Georg Thieme Verlag Stuttgart.

In Situ Synthesis of CuN4/Mesoporous N-Doped Carbon for Selective Oxidative Crosscoupling of Terminal Alkynes under Mild Conditions

The 1,3-conjugated diynes are an important class of chemical intermediates, and the selective crosscoupling of terminal alkynes is an efficient chemical process for manufacturing asymmetrical 1,3-conjugated diynes. However, it often occurs in homogenous conditions and costs a lot for reaction treatment. Herein, a copper catalyzed strategy is used to synthesize highly ordered mesoporous nitrogen-doped carbon material (OMNC), and the copper species is in situ transformed into the copper single-atom site with four nitrogen coordination (CuN4). These features make the CuN4/OMNC catalyst efficient for selective oxidative crosscoupling of terminal alkynes, and a wide range of asymmetrical and symmetrical 1,3-diynes (26 examples) under mild conditions (40?°C) and low substrates ratio (1.3). Density functional theory (DFT) calculations reveal that the aryl–alkyl crosscoupling has the lowest energy barrier on the CuN4 site, which can explain the high selectivity. In addition, the catalyst can be separated and reused by simply centrifugation or filtration. This work can open a facile avenue for constructing single-atom loaded mesoporous materials to bridge homogeneous and heterogeneous catalysis.

Tuning of cross-Glaser products mediated by substrate-catalyst polymeric backbone interactions

Tuning of cross-Glaser products using different polymeric backbones supported by copper oxide nano-catalysts has been demonstrated by tweaking the substrate-catalyst interactions under greener conditions. Further, highly reactive magnetically separable and recyclable catalyst with scalability is demonstrated.

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.

Metallomicelle catalyzed aerobic tandem desilylation/Glaser reaction in water

PEG-grafted nitrogen ligands were synthesized. The corresponding copper complexes serve as metallomicellar nanoreactors for the aerobic tandem desilylation/Glaser coupling of TMS-protected alkynes in water. The protocol is also suitable for base-free homocoupling of terminal alkynes. The metallomicellar catalyst could be recycled 5 times with minor loss of reactivity.

Transition-Metal-Free Synthesis of Borylated Thiophenes via Formal Thioboration

A simple, regiocontrolled, and transition-metal-free approach to access exclusively 3-borylated thiophene derivatives is reported. The commercially available B-chlorocatecholborane reagent (ClBcat) acts as a carbophilic Lewis acid to activate the alkyne i

Glaser-Hay hetero-coupling in a bimetallic regime: A Ni(II)/Ag(i) assisted base, ligand and additive free route to selective unsymmetrical 1,3-diynes

A Ni(OAc)2/Ag(OTf) catalysed coupling of aryl alkynes and propargylic alcohol/ether/ester gave the corresponding unsymmetrical 1,3-diynes in good to excellent yields. The reaction does not require bases, ligands or additives and shows excellent hetero-selectivity, thereby addressing the current challenges in the field of coupling of two different terminal alkynes.

Copper Catalysis for Selective Heterocoupling of Terminal Alkynes

A Cu-catalyzed selective aerobic heterocoupling of terminal alkynes is disclosed, which enables the synthesis of a broad range of unsymmetrical 1,3-diynes in good to excellent yields. The results disprove the long-held belief that homocouplings are exclusively favored in the Glaser-Hay reaction.