Deep Eutectic Solvent-Mediated Oxidative Homocoupling of Terminal Alkynes to 1,3-Diynes under Mild Green Conditions

被引:0
|
作者
Bhise, Rupali S. S. [1 ]
Ghorpade, Prashant V. V. [1 ]
Mehta, Viral R. R. [1 ]
Shankarling, Ganapati S. S. [1 ]
机构
[1] Inst Chem Technol, Dept Specialty Chem Technol, NP Marg, Mumbai 400019, India
来源
CHEMISTRYSELECT | 2023年 / 8卷 / 15期
关键词
Alkyne; C-C coupling; Deep eutectic solvents; Greener protocol; Recyclability; EFFICIENT; MIXTURES; OXIDANT;
D O I
10.1002/slct.202203985
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We prepared a commercially viable Deep Eutectic Solvent (DES) based on Choline Chloride-Urea-copper acetate for the first time. It mediates the homocoupling of terminal alkynes, using air as an oxidant. Water is the only by-product of the entire process. The method avoids ligands, bases, oxidants, and costly palladium catalysts, which qualifies the process greener than ever. The DES can be reused at least three times without affecting the reaction yield significantly. The key features of the protocol that qualify the process as green include the ambient reaction temperatures, lesser use of conventional organic solvents in the reaction, higher yields, and easy product isolation qualify the protocol as a green process.
引用
收藏
页数:5
相关论文
共 50 条
  • [21] Copper catalyzed oxidative homocoupling of terminal alkynes to 1,3-diynes: a Cu3(BTC)2MOF as an efficient and ligand free catalyst for Glaser-Hay coupling
    Devarajan, Nainamalai
    Karthik, Murugan
    Suresh, Palaniswamy
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (43) : 9191 - 9199
  • [22] An Efficient and Versatile Deep Eutectic Solvent-Mediated Green Method for the Synthesis of Functionalized Coumarins
    Rather, Ishfaq Ahmad
    Ali, Rashid
    ACS OMEGA, 2022, 7 (12): : 10649 - 10659
  • [23] Zinc-mediated enantioselective addition of terminal 1,3-diynes to N-arylimines of trifluoropyruvates
    Zhang, Fa-Guang
    Ma, Hai
    Zheng, Yan
    Ma, Jun-An
    TETRAHEDRON, 2012, 68 (37) : 7663 - 7669
  • [24] Radical-mediated carboselenation of terminal alkynes under mild conditions
    Ma, Chixiao
    Xie, Jingli
    Zeng, Xianghua
    Wei, Zheyu
    Wei, Yongge
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (16): : 4441 - 4446
  • [25] Requirement for an oxidant in Pd/Cu co-catalyzed terminal alkyne homocoupling give symmetrical 1,4-disubstituted 1,3-diynes
    Batsanov, AS
    Collings, JC
    Fairlamb, IJS
    Holland, JP
    Howard, JAK
    Lin, ZY
    Marder, TB
    Parsons, AC
    Ward, RM
    Zhu, J
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02): : 703 - 706
  • [26] Rhodium-catalysed homo-coupling of terminal alkynes: divergent synthesis of bioactive 1,3-diynes and conjugated enediynes
    Xiao, Yijie
    Lv, Lijie
    Luo, Nanxuan
    Zhao, Peirui
    Chen, Yao
    Luo, Zhangshun
    Yin, Houhua
    He, Yi
    Nie, Shenyou
    NEW JOURNAL OF CHEMISTRY, 2024, 48 (16) : 7517 - 7523
  • [27] Synthesis of Unsymmetrical 1,3-Diynes via Pd/Cu-Catalyzed Cross-Coupling of Terminal Alkynes at Room Temperature
    Liu, Yashuai
    Liu, Ping
    Gu, Ningning
    Xie, Jianwei
    Liu, Yan
    Dai, Bin
    CHINESE JOURNAL OF CHEMISTRY, 2016, 34 (09) : 895 - 900
  • [28] Homocoupling of terminal alkynes catalyzed by copper complexes of 1,10-phenanthroline under base- and solvent-free conditions
    Chia, Poh Wai
    Ruslan, Nur Aimi Aqilah Ahmad
    Yong, Fu Siong Julius
    Kan, Su-Yin
    KUWAIT JOURNAL OF SCIENCE, 2020, 47 (02) : 41 - 49
  • [29] Transition-Metal-Free Synthesis of Symmetrical 1,4-Diarylsubstituted 1,3-Diynes by Iodine-Mediated Decarboxylative Homocoupling of Arylpropiolic Acids
    Ghosh, Subhankar
    Chattopadhyay, Shital Kumar
    TETRAHEDRON LETTERS, 2022, 102
  • [30] Cu (I) immobilized on functionalized SBA-15: A recyclable catalyst for the synthesis of 1,3-diynes using terminal alkynes without base
    Ma, Zongyan
    Wang, Xiaoyu
    Wei, Shuoyun
    Yang, Honglei
    Zhang, Fengwei
    Wang, Peng
    Xie, Miao
    Ma, Jiantai
    CATALYSIS COMMUNICATIONS, 2013, 39 : 24 - 29