1101205-12-2Relevant academic research and scientific papers
In Situ Synthesis of CuN4/Mesoporous N-Doped Carbon for Selective Oxidative Crosscoupling of Terminal Alkynes under Mild Conditions
Cao, Yue,Gu, Dong,Lei, Aiwen,Liang, Zhenjin,Su, Yaqiong,Wu, Jinsong,Wu, Yong,Xiao, Wei,Yang, Dali,Yu, Ruohan,Zhang, Dongchao,Zhang, Yuanteng
, (2021/12/23)
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.
Copper Catalysis for Selective Heterocoupling of Terminal Alkynes
Su, Lebin,Dong, Jianyu,Liu, Long,Sun, Mengli,Qiu, Renhua,Zhou, Yongbo,Yin, Shuang-Feng
supporting information, p. 12348 - 12351 (2016/10/07)
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.
Homo and heterocoupling of terminal alkynes using catalytic CuCl 2 and DBU
Balamurugan, Rengarajan,Naveen, Naganaboina,Manojveer, Seetharaman,Nama, Masthan Vali
experimental part, p. 567 - 575 (2012/01/02)
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.
Copper(I) iodide catalyzed cross-coupling reaction of terminal alkynes with 1-bromoalkynes: A simple synthesis of unsymmetrical buta-1,3-diynes
Wang, Shihua,Yu, Lin,Li, Pinhua,Meng, Lingguo,Wang, Lei
experimental part, p. 1541 - 1546 (2011/06/25)
A simple synthesis of unsymmetrical buta-1,3-diynes by cross-coupling of terminal alkynes with 1-bromoalkynes in the presence of copper(I) iodide and tris(o-tolyl)phosphine was developed that gives good yields under simple and mild reaction conditions. The scope and limitations of the cross-coupling reaction were investigated. Georg Thieme Verlag Stuttgart · New York.
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
Yin, Weiyan,He, Chuan,Chen, Mao,Zhang, Heng,Lei, Aiwen
scheme or table, p. 709 - 712 (2009/08/12)
(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.
