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
  • [1] Hydroxylamines as oxidation catalysts: Thermochemical and kinetic studies
    Amorati, R
    Lucarini, M
    Mugnaini, V
    Pedulli, GF
    Minisci, F
    Recupero, F
    Fontana, F
    Astolfi, P
    Greci, L
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) : 1747 - 1754
  • [2] Proton-electron transfer pathways in the reactions of peroxyl and dpph• radicals with hydrogen-bonded phenols
    Amorati, Riccardo
    Menichetti, Stefano
    Viglianisi, Caterina
    Foti, Mario C.
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (97) : 11904 - 11906
  • [3] AN ELECTRON-SPIN RESONANCE STUDY OF THE SUPEROXIDE RADICAL-ANION IN POLYCRYSTALLINE MAGNESIUM-OXIDE AND TITANIUM-DIOXIDE POWDERS
    AMORELLI, A
    EVANS, JC
    ROWLANDS, CC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS I, 1988, 84 : 1723 - 1728
  • [4] [Anonymous], 2004, ACS SYM SER
  • [5] [Anonymous], 2007, ANGEW CHEM
  • [6] [Anonymous], 2011, Angew. Chem
  • [7] Synthesis of naphthalenediols by aerobic oxidation of diisopropylnaphthalenes catalyzed by N-hydroxyphthalimide (NHPI)/α,α′-azobisisobutyronitrile (AIBN)
    Aoki, Y
    Sakaguchi, S
    Ishii, Y
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (2-3) : 199 - 202
  • [8] Selective catalytic oxidation of cyclohexylbenzene to cyclohexylbenzene-1-hydroperoxide:: a coproduct-free route to phenol
    Arends, IWCE
    Sasidharan, M
    Kühnle, A
    Duda, M
    Jost, C
    Sheldon, RA
    [J]. TETRAHEDRON, 2002, 58 (44) : 9055 - 9061
  • [9] Hydrogen abstraction from ethylbenzene by imide-N-oxyl radicals with and without O2:: a DFT theoretical study
    Arnaud, R
    Milet, A
    Adamo, C
    Einhorn, C
    Einhorn, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2002, (12): : 1967 - 1972
  • [10] Astruc D., 2008, NANOPARTICLES CATALY