136053-56-0Relevant articles and documents
First report of a nano-Cu2O-catalyzed protocol for homo-coupling reaction of terminal alkynes in water/ionic liquid medium
Tang, Bo-Xiao,Fang, Xiao-Niu,Kuang, Ren-Yun,Wu, Jian-Hong,Chen, Qiao,Hu, Shao-Jun,Liu, Yi-Lin
, p. 943 - 945 (2016)
A new, efficient and green protocol for the nano-Cu2O-catalyzed homo-coupling reaction of terminal alkynes has been developed, using water/ionic liquid as an environmentally friendly solvent. Moreover, the system also allows the synthesis of unsymmetric 1,3-diynes by cross-coupling of two different terminal alkynes. It is noteworthy that the nano-Cu2O-catalyzed methodology is a good supplement to copper catalyst for the Glaser-type homo-coupling reaction. Copyright
Silver-catalyzed Glaser coupling of alkynes
Mo, Guoli,Tian, Zaimin,Li, Jiping,Wen, Guohua,Yang, Xiaomin
, p. 231 - 233 (2015)
Excellent yields were obtained from the silver nitrate-catalyzed homocoupling reaction of alkynes in N,N-dimethylformamide using triphenylphosphine as ligand. This safe and simple silver catalytic system has been employed in a safe and efficient protocol
One-pot synthesis of 1,4-diarylsubstituted 1,3-diynes from the sequential coupling reactions of aryl iodides and propiolic acid
Kim, Yong,Park, Ahbyeol,Park, Kyungho,Lee, Sunwoo
, p. 1766 - 1769 (2011)
1,4-Disubstituted 1,3-dialkynes were obtained from the one-pot palladium/copper-catalyzed coupling reactions of aryl iodide and propiolic acid. The optimized catalytic system consisted of 5.0 mol % Pd(PPh3) 2Cl2, 10 mol % dppb, 10 mol % CuI, 2.4 equiv of DBU, and 1.2 equiv of K2CO3. The coupling reaction was carried out at 30 °C for 6 h and subsequently at 80 °C for 3 h.
Heterogeneously catalyzed efficient alkyne-alkyne homocoupling by supported copper hydroxide on titanium oxide
Oishi, Takamichi,Katayama, Tatsuyori,Yamaguchi, Kazuya,Mizuno, Noritaka
, p. 7539 - 7542 (2009)
The role of the supported Copper Hydroxide on Titanium Oxide as an efficient heterogeneous catalyst for the oxidative alkyne-alkyne homocoupling was analyzed. The catalytic activities for the homocoupling of ethynylbenzene to 1,4-diphenyl-1,3-butadiyne were compared with various catalysts in toluene under oxygen atmosphere. No homocoupling reaction proceeded with bulk copper oxides and hydroxide. The inductively coupled plasma atomic emission spectroscopy analysis revealed that no copper species was found in the filtrate. Therefore, the role of the copper hydroxide species is probably the abstraction of an alkyne hydrogen to form the alkynyl species. The supported copper hydroxide could act as an efficient heterogenous catalyst for the oxidative alkyne-alkyne homocoupling.
Copper(i)-catalyzed homo-coupling of terminal alkynes at room temperature under solvent and base free conditions using O2 as an oxidant
Cheng, Guolin,Zhang, Hong,Cui, Xiuling
, p. 1849 - 1852 (2014)
The homo-coupling of various terminal alkynes were realized in the presence of 0.5 mol% CuI and 5 mol% benzylamine. This transformation proceeded at room temperature under solvent and base free conditions using O2 as an oxidant. The TON was up to 1760.
Synthesis and structural characterization of a monomeric di-copper-substituted silicotungstate [γ-H2SiW10O36Cu2(μ-1,1-N3)2]4- and the catalysis of oxidative homocoupling of alkynes
Yamaguchi, Kazuya,Kamata, Keigo,Yamaguchi, Syuhei,Kotani, Miyuki,Mizuno, Noritaka
, p. 121 - 130 (2008)
The di-copper-substituted γ-Keggin silicotungstate with bis-μ-1,1-azido ligands TBA4[γ-H2SiW10O36Cu2(μ-1,1-N3)2] (1, TBA = tetra-n-butylammonium) was synthesized in an aqueous medium. The crystal structure of the anion part of 1 was a monomer of the basal-basal end-on diazido-bridged di-copper-substituted γ-Keggin silicotungstate. The NMR and CSI-MS spectra of 1 in organic solvents, such as acetonitrile, benzonitrile, and 1,2-dichloroethane, showed that complex 1 was present as a monomer of the di-copper-substituted γ-Keggin silicotungstate. Complex 1 could act as an effective homogeneous catalyst for the oxidative homocoupling of various types of alkynes, including aromatic, aliphatic, and heteroatom-containing ones. The reaction possibly proceeds as follows: First, the ligand exchange proceeds between the azido groups in 1 and alkynyl groups to form the corresponding diyne with the reduced copper(I) species via the di-copper(II)-alkynyl intermediate, then the reduced species is reoxidized by molecular oxygen, and the oxidized species reacts with an alkyne to regenerate the alkynyl intermediate.
Cu(ii)@Luviset clear as recyclable catalyst for the formation of C-C bond in homo-coupling of terminal alkynes
Wang, Zheng-Jun,Wang, Peng-Hui,Lv, Jing-Jing,Feng, Jiu-Ju,Xu, Xinhua,Wang, Ai-Jun,Au, Chak-Tong,Qiu, Renhua
, p. 96372 - 96376 (2015)
Commercial copolymer Luviset clear (L1), an environmentally benign and efficient ligand, was used to facilitate the catalytic performance of Cu(NO3)2 for homo-coupling of terminal alkynes. A series of substituted aromatic and aliphat
Method for preparing conjugated diyne compound by using copper complex
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Paragraph 0053-0058; 0059-0060; 0065-0066; ..., (2021/07/14)
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.
Synthesis, Characterization of Spirocyclic λ3-Iodanes and Their Application to Prepare 4,1-Benzoxazepine-2,5-diones and 1,3-Diynes
Sun, Xu,Guo, Xiao-Qiang,Chen, Lian-Mei,Kang, Tai-Ran
, p. 4312 - 4316 (2021/02/06)
Herein, a [3+2] cycloaddition of aza-oxyallylic cations with ethynylbenziodoxolones for synthesis of new λ3-iodanes containing spirocyclic 4-oxazolidinone has been developed. This cyclic λ3-iodanes display stability in air and excellent solubility in organic solvent. Using them as substrate, both the 4,1-benzoxazepine-2,5-diones and symmetrical 1,3-diynes derivatives were afforded in high yield under copper(I)-catalyzed conditions.
