Supported gold nanoparticles catalyzed cis-selective semihydrogenation of alkynes using ammonium formate as the reductant

被引:41
|
作者
Liang, Shengzong [1 ]
Hammond, Gerald B. [1 ]
Xu, Bo [2 ]
机构
[1] Univ Louisville, Dept Chem, Louisville, KY 40292 USA
[2] Donghua Univ, Coll Chem Chem Engn & Biotechnol, 2999 North Renmin Lu, Shanghai 201620, Peoples R China
基金
美国国家科学基金会;
关键词
PALLADIUM; HYDROGENATION; ACTIVATION; FLUORINE; DIFLUOROMETHYLATION; SEMIREDUCTION; ACETYLENE; MIXTURES; LACTONE; REAGENT;
D O I
10.1039/c6cc01318j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
TiO2 supported gold nanoparticles with low loading (0.5 mol%) are able to semihydrogenate non -fluorinated and gem-difluorinated alkynes to cis-alkenes with high selectivity, using cost-effective and easy-to-handle ammonium formate as the reductant. No over-reduction was observed. The good recyclability of Au/TiO2 allows for "green" semireduction of alkynes. A difluorinated pyran and ce,p-unsaturated 8-lactone were easily prepared from the obtained gem-difluoro alkene building blocks.
引用
收藏
页码:6013 / 6016
页数:4
相关论文
共 50 条
  • [1] Supported Gold Nanoparticle-Catalyzed cis-Selective Disilylation of Terminal Alkynes by σ Disilanes
    Gryparis, Charis
    Kidonakis, Marios
    Stratakis, Manolis
    ORGANIC LETTERS, 2013, 15 (23) : 6038 - 6041
  • [2] cis-Selective Transfer Semihydrogenation of Alkynes by Merging Visible-Light Catalysis with Cobalt Catalysis
    Tian, Wan-Fa
    He, Yong-Qin
    Song, Xian-Rong
    Ding, Hai-Xin
    Ye, Jing
    Guo, Wen-Jie
    Xiao, Qiang
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (05) : 1032 - 1038
  • [3] Trans- and cis-selective Lewis acid catalyzed hydrogermylation of alkynes
    Schwier, T
    Gevorgyan, V
    ORGANIC LETTERS, 2005, 7 (23) : 5191 - 5194
  • [4] cis-Semihydrogenation of alkynes with amine borane complexes catalyzed by gold nanoparticles under mild conditions
    Vasilikogiannaki, Eleni
    Titilas, Ioannis
    Vassilikogiannakis, Georgios
    Stratakis, Manolis
    CHEMICAL COMMUNICATIONS, 2015, 51 (12) : 2384 - 2387
  • [5] Highly efficient and cis-selective carbofunctionalization of internal alkynes catalyzed by palladium a-diimine complexes
    Zhang, Yu
    Du, Sheng-Nan
    Guo, Mia
    Wu, Xiao Meng
    Yu, Yong Yi
    Liu, Feng-Shou
    Xu, Chang
    MOLECULAR CATALYSIS, 2023, 549
  • [6] Selective Semihydrogenation of Alkynes with N-Graphitic-Modified Cobalt Nanoparticles Supported on Silica
    Chen, Feng
    Kreyenschulte, Carsten
    Radnik, Joerg
    Lund, Henrik
    Surkus, Annette-Enrica
    Junge, Kathrin
    Beller, Matthias
    ACS CATALYSIS, 2017, 7 (03): : 1526 - 1532
  • [7] Highly Chemo- and Regioselective Transfer Reduction of Aromatic Nitro Compounds using Ammonium Formate Catalyzed by Supported Gold Nanoparticles
    Lou, Xia-Bing
    He, Lin
    Qian, Yue
    Liu, Yong-Mei
    Cao, Yong
    Fan, Kang-Nian
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (2-3) : 281 - 286
  • [8] PVC-NHC-Pd(0): An efficient and reusable heterogeneous catalyst for highly cis-selective semihydrogenation of alkynes using formic acid as hydrogen source
    Zheng, Waner
    Zhou, Yuemin
    Li, Yiqun
    INORGANIC CHEMISTRY COMMUNICATIONS, 2021, 134
  • [9] Application of Pd Nanoparticles Supported on Mesoporous Hollow Silica Nanospheres for the Efficient and Selective Semihydrogenation of Alkynes
    Verho, Oscar
    Zheng, Haoquan
    Gustafson, Karl P. J.
    Nagendiran, Anuja
    Zou, Xiaodong
    Backvall, Jan-E.
    CHEMCATCHEM, 2016, 8 (04) : 773 - 778
  • [10] Highly efficient and cis-selective semihydrogenation of dialkyl alkynes with EtOH enforced by a catalyst-state induced color-change strategy
    Zhuangxing Li
    Guixia Liu
    Zheng Huang
    Science China(Chemistry), 2025, 68 (04) : 1392 - 1401