A ligand-free in situ-generated cobalt nanoparticle catalyst for (Z)-selective transfer semihydrogenation of alkynes

被引:0
|
作者
Yang, Shunbin [1 ]
Zhang, Dengju [1 ]
Zuo, Weiguo [2 ]
Wang, Guanqun [1 ]
Wang, Chengtao [1 ]
Guo, Jiyang [2 ]
Fan, Duona [1 ]
You, Song [2 ]
Jia, Xian [1 ]
机构
[1] Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, Shenyang 110016, Peoples R China
[2] Shenyang Pharmaceut Univ, Sch Life Sci & Biopharmaceut Sci, Shenyang 110016, Peoples R China
基金
中国国家自然科学基金;
关键词
SPENT AMMONIA BORANE; TRANSFER HYDROGENATION; STEREOSELECTIVE SEMIHYDROGENATION; HYDROSILYLATION; ALKENES; ETHANOL;
D O I
10.1039/d3nj01943h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, we developed a simple and efficient approach for the (Z)-selective transfer semihydrogenation of alkynes based on in situ-generated cobalt nanoparticles (CoNPs) and ammonia-borane (NH3.BH3), in which aryl-aryl, aryl-alkyl and terminal alkynes were converted to their (Z)-alkenes in good to excellent yields (72-96%). The heterogeneous and magnetic properties of CoNPs make them easy to separate from the reaction system, and the recovered CoNPs could be reused six times without significant loss of catalytic activity. Moreover, our method also enabled us to prepare combretastatin A-4 (CA-4) at gram scale.
引用
收藏
页码:18634 / 18639
页数:6
相关论文
共 50 条
  • [21] Efficient Carboxylation of Terminal Alkynes with Carbon Dioxide Catalyzed by Ligand-Free Copper Catalyst under Ambient Conditions
    Wang, Wan-Hui
    Jia, Lihong
    Feng, Xiujuan
    Fang, Dingqiao
    Guo, Hongyu
    Bao, Ming
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (08) : 1501 - 1505
  • [22] Reductive Amination of Aldehyde and Ketone with Ammonia and H2 by an In Situ-Generated Cobalt Catalyst under Mild Conditions
    Zhang, Shiyun
    Hu, Yue
    Li, Meichao
    Xie, Yinjun
    ORGANIC LETTERS, 2024, 26 (34) : 7122 - 7127
  • [23] Self-Assembled Multilayer-Stabilized Nickel Nanoparticle Catalyst for Ligand-Free Cross-Coupling Reactions: in situ Metal Nanoparticle and Nanospace Simultaneous Organization
    Hoshiya, Naoyuki
    Fujiki, Katsumasa
    Taniguchi, Takahisa
    Honma, Tetsuo
    Tamenori, Yusuke
    Xiao, Mincen
    Saito, Nozomi
    Yokoyama, Mami
    Ishii, Akira
    Fujioka, Hiromichi
    Shuto, Satoshi
    Sato, Yoshihiro
    Arisawa, Mitsuhiro
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (15) : 2449 - 2459
  • [24] Catalyst-Free Conjugate Addition of Indolizines to In Situ-Generated Oxidized Morita-Baylis-Hillman Adducts
    Silva, Thiago S.
    Zeoly, Lucas A.
    Coelho, Fernando
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (08): : 5438 - 5448
  • [25] Ligand-free gold–silver nanoparticle alloy polymer composites generated by picosecond laser ablation in liquid monomer
    Ana Menéndez-Manjón
    Andreas Schwenke
    Timo Steinke
    Matthias Meyer
    Ulrich Giese
    Philipp Wagener
    Stephan Barcikowski
    Applied Physics A, 2013, 110 : 343 - 350
  • [26] Highly selective a-hydrogermylation of alkynes catalyzed by an in situ generated bulky NHC-cobalt complex
    Bolt, Malgorzata
    Mermela, Aleksandra
    Zak, Patrycja
    CHEMICAL COMMUNICATIONS, 2023, 59 (77) : 11548 - 11551
  • [27] Palladium nanodendrites uniformly deposited on the surface of polymers as an efficient and recyclable catalyst for direct drug modification via Z-selective semihydrogenation of alkynes
    Garcia-Calvo, Jose
    Calvo-Gredilla, Patricia
    Vallejos, Saul
    Miguel Garcia, Jose
    Vicente Cuevas-Vicario, Jose
    Garcia-Herbosa, Gabriel
    Avella, Manuel
    Torroba, Tomas
    GREEN CHEMISTRY, 2018, 20 (16) : 3875 - 3883
  • [28] Ligand-free gold-silver nanoparticle alloy polymer composites generated by picosecond laser ablation in liquid monomer
    Menendez-Manjon, Ana
    Schwenke, Andreas
    Steinke, Timo
    Meyer, Matthias
    Giese, Ulrich
    Wagener, Philipp
    Barcikowski, Stephan
    APPLIED PHYSICS A-MATERIALS SCIENCE & PROCESSING, 2013, 110 (02): : 343 - 350
  • [29] Efficient and selective external activator-free cobalt catalyst for hydroboration of terminal alkynes enabled by BiPyPhos
    Li, Zheng
    Zhao, Jiangui
    Xue, Weichao
    Tang, Juan
    Li, Shun
    Ge, Yicen
    Xu, Jiaqi
    Zheng, Xueli
    Li, Ruixiang
    Chen, Hua
    Fu, Haiyan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (22) : 4455 - 4460
  • [30] Aerobic ligand-free Suzuki coupling reaction of aryl chlorides catalyzed by in situ generated palladium nanoparticles at room temperature
    Han, Wei
    Liu, Chun
    Jin, Zilin
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) : 501 - 508