Gold Nanoparticle-Polydopamine-Reduced Graphene Oxide Ternary Nanocomposite as an Efficient Catalyst for Selective Oxidation of Benzylic C(sp3)-H Bonds Under Mild Conditions

被引:42
作者
Majumdar, Biju [1 ]
Bhattacharya, Tamalika [1 ]
Sarma, Tridib K. [1 ]
机构
[1] Indian Inst Technol, Sch Basic Sci, Discipline Chem, Khandwa Rd, Indore 452020, Madhya Pradesh, India
关键词
graphene; heterogeneous catalysis; nanoparticles; oxidation; supported catalysts; N-HYDROXYPHTHALIMIDE NHPI; PD ALLOY NANOPARTICLES; C-H BONDS; MOLECULAR-OXYGEN; AEROBIC OXIDATION; VISIBLE-LIGHT; HYDROCARBON OXIDATION; HYDROGEN ABSTRACTION; ELECTRON-TRANSFER; ALKANE OXIDATION;
D O I
10.1002/cctc.201600136
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A ternary nanocomposite comprising of Au nanoparticles (NPs), polydopamine, and reduced graphene oxide exhibits excellent activity and selectivity towards the oxidation of C-H bonds in benzylic hydrocarbons under mild conditions in the presence of N-hydroxyphthalimide. All the components in the nanocomposite play an important role in the effectiveness of the catalyst. Sufficient electron transfer from polydopamine to the Au NPs afforded a more negatively charged nanoparticle surface and was favorable for molecular oxygen activation, leading to C-H bond oxidation. The reaction followed a free radical pathway as shown by detailed mechanistic studies. Further, easy separation and excellent reusability without significant loss in activity over several iterations make the ternary nanocomposite an excellent heterogeneous catalyst for C-H oxidation reactions.
引用
收藏
页码:1825 / 1835
页数:11
相关论文
共 105 条
  • [21] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation
    Colby, Denise A.
    Bergman, Robert G.
    Ellman, Jonathan A.
    [J]. CHEMICAL REVIEWS, 2010, 110 (02) : 624 - 655
  • [22] C-H Bond Activation Reactions of Ethers That Generate Iridium Carbenes
    Conejero, Salvador
    Paneque, Margarita
    Poveda, Manuel L.
    Santos, Laura L.
    Carmona, Ernesto
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (04) : 572 - 580
  • [23] Spin Trapping of Au-H Intermediate in the Alcohol Oxidation by Supported and Unsupported Gold Catalysts
    Conte, Marco
    Miyamura, Hiroyuki
    Kobayashi, Shu
    Chechik, Victor
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (20) : 7189 - 7196
  • [24] Supported gold nanoparticles as catalysts for organic reactions
    Corma, Avelino
    Garcia, Hermenegildo
    [J]. CHEMICAL SOCIETY REVIEWS, 2008, 37 (09) : 2096 - 2126
  • [25] Unravelling the origin of the high-catalytic activity of supported Au:: A density-functional theory-based interpretation
    Cruz Hernandez, Norge
    Fdez. Sanz, Javier
    Rodriguez, Jose A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (49) : 15600 - 15601
  • [26] Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion
    Davies, Huw M. L.
    Manning, James R.
    [J]. NATURE, 2008, 451 (7177) : 417 - 424
  • [27] Selective formation of lactate by oxidation of 1,2-propanediol using gold palladium alloy supported nanocrystals
    Dimitratos, Nikolaos
    Lopez-Sanchez, Jose Antonio
    Meenakshisundaram, Sankar
    Anthonykutty, Jinto Manjaly
    Brett, Gemma
    Carley, Albert F.
    Taylor, Stuart H.
    Knight, David W.
    Hutchings, Graham J.
    [J]. GREEN CHEMISTRY, 2009, 11 (08) : 1209 - 1216
  • [28] Ding S.T., 2012, ANGEW CHEM, V124, P9360
  • [29] Establishing a Au Nanoparticle Size Effect in the Oxidation of Cyclohexene Using Gradually Changing Au Catalysts
    Donoeva, Baira G.
    Ovoshchnikov, Daniil S.
    Golovko, Vladimir B.
    [J]. ACS CATALYSIS, 2013, 3 (12): : 2986 - 2991
  • [30] Graphite oxide as a carbocatalyst for the preparation of fullerene-reinforced polyester and polyamide nanocomposites
    Dreyer, Daniel R.
    Jarvis, Karalee A.
    Ferreira, Paulo J.
    Bielawski, Christopher W.
    [J]. POLYMER CHEMISTRY, 2012, 3 (03) : 757 - 766