219631-28-4

Upstream product

• 4094-90-0 (3-iodoprop-2-ynyloxymethyl)benzene 
• 4039-82-1 Benzyl propargyl ether 
• 89343-06-6 tris-iso-propylsilyl acetylene 
• 218431-34-6 (((3-bromoprop-2-yn-1-yl)oxy)methyl)benzene 
• 100-51-6 benzyl alcohol 
• 931-49-7 1-ethenylcyclohexene 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 536-74-3 phenylacetylene 
• 552-16-9 ortho-nitrobenzoic acid 

Relevant academic research and scientific papers

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.

Synthesis of Aryl Alkynes via Copper Catalyzed Decarboxylative Alkynylation of 2-Nitrobenzoic Acids

An efficient protocol for the synthesis of internal aryl alkynes was achieved via Cu-catalyzed decarboxylative cross-coupling reactions, and to the best of our knowledge, this is the first example of a Cu-catalyzed decarboxylative alkynylation of benzoic acids with terminal alkynes. This approach utilizes simple Cu salt as catalyst and O2, an abundant, clean, and green material, as the oxidant. The reaction tolerates various functional groups, and a variety of internal aryl alkynes were synthesized in 46-83% yields.

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.

Nonafluorobutanesulfonyl azide as a shelf-stable highly reactive oxidant for the copper-catalyzed synthesis of 1,3-diynes from terminal alkynes

Nonafluorobutanesulfonyl azide is a highly efficient reagent for the copper-catalyzed coupling of terminal alkynes to give symmetrical and unsymmetrical 1,3-diynes in good to excellent yields and with good functional group compatibility. The reaction is e

A mild CuI-catalyzed Glaser-type homo-coupling reaction using α,α-dibromo-β-dicarbonyl compounds as oxidants

Exploration of α,α-dibromo-β-dicarbonyl compounds as novel organic oxidants for the mild Cu(I)-catalyzed Glaser-type homo-coupling reaction has been achieved, which provides an alternatively efficient pathway for the construction of 1,3-conjugated structures. In addition, the mechanism of this reaction was investigated.

A facile copper(i)-catalyzed homocoupling of terminal alkynes to 1,3-diynes with diaziridinone under mild conditions

A novel and efficient Cu(i)-catalyzed oxidative homocoupling of terminal alkynes with diaziridinone as an oxidant is described. Various terminal alkynes can be transformed into the corresponding 1,3-diynes in good yields. The reaction process is base-free

Homo and heterocoupling of terminal alkynes using catalytic CuCl 2 and DBU

Homocoupling of terminal alkynes has been efficiently achieved using catalytic amounts of CuCl2 and DBU. This methodology could be extended to couple two different terminal alkynes together by taking one of the alkyne partners, preferably the electron rich alkyne, in five fold excess than the other. CSIRO 2011.

Nickel-catalyzed oxidative coupling reactions of two different terminal alkynes using O2 as the oxidant at room temperature: Facile syntheses of unsymmetric 1,3-diynes

(Formula Presented) Two different terminal alkynes now can be coupled together in the presence of NiCl2-6H2O/Cul by using an excess of one of the terminal alkyne substrates. The new method employed 20 mol % TMEDA as the ligand and environmentally benign O2 or air as the oxidant. It is the first example using Ni-salt as catalyst by employing air or O2 as oxidant, which led to efficient heterocoupling of two different alkynes.

Copper powder-mediated homocoupling reactions of iodoacetylenes to synthesize symmetrical 1,3-butadiynes

A new route to synthesize symmetrical 1,3-butadiynes from iodoacetylenes in the presence of copper powder and pyridine was developed. Moderate to excellent yields were obtained through an efficient and simple process involving the copper powder without any further activation. Copyright Taylor & Francis Group, LLC.