24996-65-4

Upstream product

• 6750-04-5 propargyl benzoate 
• 622-79-7 benzyl azide 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 705-31-7 4-trifluoromethylphenylacetylene 
• 536-74-3 phenylacetylene 
• 98-88-4 benzoyl chloride 
• 3031-68-3 Hexa-2,4-diyne-1,6-diol 

Downstream Products

• 112503-79-4 C₂₁H₁₆N₂O₄ 

Relevant academic research and scientific papers

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 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.

Efficient copper(II) acetate catalyzed homo- and heterocoupling of terminal alkynes at ambient conditions

Symmetrical 1,3-diynes were obtained in quantitative yields using the copper(II) acetate catalyzed homocoupling of terminal alkynes in the presence of a stoichiometric amount of piperidine at 25 °C under aerobic conditions. We also accomplished facile syntheses of unsymmetric 1,3-diynes by heterocoupling terminal alkynes in very good yields under the reported reaction conditions. Georg Thieme Verlag Stuttgart.

Alkynylcopper(i) polymers and their use in a mechanistic study of alkyne-azide click reactions

Polymeric dinuclear alkynylcopper(i) complexes, for example phenylethynylcopper(i), can be prepared by a robust method involving the interaction of terminal alkynes with copper(ii) salts in acetonitrile. The use of the ladder polymers provides heterogeneous catalysts for copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions and provides important mechanistic information.

Ligand- and base-free synthesis of 1,3-diynes catalyzed by low loading of heterogeneous Pd/C and CuI

A facile and environmentally friendly synthetic method for a variety of symmetrical 1,3-diyne derivatives based on the Pd/C-CuI-catalyzed homocoupling reaction of terminal alkynes has been developed. The reaction was efficiently catalyzed by the extremely

Alternating diacetylene copolymer utilizing perfluorophenyl-phenyl interactions

The symmetric diacetylenes, 2,4-hexadiynylene dibenzoate 4 and 2,4-hexadiynylene bis-(pentafluorobenzoate) 5, as well as the unsymmetric 6-(pentafluorobenzoyloxy)hexa-2,4-diynyl benzoate 6 were prepared and investigated with respect to their reactivity toward topochemical polymerization in the crystalline state. The 1:1 cocrystal 4-5 was successfully polymerized to the corresponding poly(diacetylene) copolymer 7, as evidenced by solid-state 13C NMR and Raman spectroscopy, as well as single-crystal structure analysis of the monomer-polymer cocrystal. Thus, perfluorophenyl-phenyl interactions were utilized as complementary supramolecular synthons in the cocrystallization of two different diacetylene monomers and their unprecedented conversion into a strictly alternating diacetylene copolymer.