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 50 条
  • [1] Catalyst-free selective oxidation of C(sp3)-H bonds in toluene on water
    Lee, Kyoungmun
    Cho, Yumi
    Kim, Jin Chul
    Choi, Chiyoung
    Kim, Jiwon
    Lee, Jae Kyoo
    Li, Sheng
    Kwak, Sang Kyu
    Choi, Siyoung Q.
    NATURE COMMUNICATIONS, 2024, 15 (01)
  • [2] Robust Bio-derived Polyoxometalate Hybrid for Selective Aerobic Oxidation of Benzylic C(sp3)-H Bonds
    Song, Jinliang
    Hua, Manli
    Huang, Xin
    Ma, Jun
    Xie, Chao
    Han, Buxing
    ACS CATALYSIS, 2023, 13 (07) : 4142 - 4154
  • [3] Organocatalytic Aerobic Oxidation of Benzylic sp3 C-H Bonds of Ethers and Alkylarenes Promoted by a Recyclable TEMPO Catalyst
    Zhang, Zhiguang
    Gao, Yuan
    Liu, Yuan
    Li, Jianjun
    Xie, Hexin
    Li, Hao
    Wang, Wei
    ORGANIC LETTERS, 2015, 17 (21) : 5492 - 5495
  • [4] Selective Oxidation of Benzylic sp3 C-H Bonds using Molecular Oxygen in a Continuous-Flow Microreactor
    Yun, Lei
    Zhao, Jingnan
    Tang, Xiaofei
    Ma, Cunfei
    Yu, Zongyi
    Meng, QingWei
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2021, 25 (07) : 1612 - 1618
  • [5] A highly reduced graphene oxide/ZrOx-MnCO3 or -Mn2O3 nanocomposite as an efficient catalyst for selective aerial oxidation of benzylic alcohols
    Assal, Mohamed E.
    Shaik, Mohammed Rafi
    Kuniyil, Mufsir
    Khan, Mujeeb
    Al-Warthan, Abdulrahman
    Siddiqui, Mohammed Rafiq H.
    Khan, Sohail M. A.
    Tremel, Wolfgang
    Tahir, Muhammad Nawaz
    Adil, Syed Farooq
    RSC ADVANCES, 2017, 7 (87) : 55336 - 55349
  • [6] Activation of C(SP3)-H Bonds Promoted Oxidation of Sulfides by O2 Under Catalyst-Free Conditions
    Wang, Zufeng
    Wang, Hongyi
    Zhao, Zhiying
    Zhu, Yu
    Deng, Youer
    Li, Xiaolong
    Zeng, Dan
    Liu, Yachun
    Zhang, Chao
    Fu, Zaihui
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2024, 46 (03): : 300 - 308
  • [7] An efficient approach for enhancing the catalytic activity of Ni-MOF-74 via a relay catalyst system for the selective oxidation of benzylic C-H bonds under mild conditions
    Guo, Changyan
    Zhang, Yonghong
    Zhang, Yi
    Wang, Jide
    CHEMICAL COMMUNICATIONS, 2018, 54 (30) : 3701 - 3704
  • [8] Radical alkylation of C(sp3)-H bonds with diacyl peroxides under catalyst-free conditions
    Tian, Hao
    Xu, Wentao
    Liu, Yuxiu
    Wang, Qingmin
    CHEMICAL COMMUNICATIONS, 2019, 55 (98) : 14813 - 14816
  • [9] Thiyl radical promoted iron-catalyzed-selective oxidation of benzylic sp3 C-H bonds with molecular oxygen
    Geng, Shasha
    Xiong, Baojian
    Zhang, Yun
    Zhang, Juan
    He, Yun
    Feng, Zhang
    CHEMICAL COMMUNICATIONS, 2019, 55 (84) : 12699 - 12702
  • [10] Ultraviolet-light-induced aerobic oxidation of benzylic C(sp3)-H of alkylarenes under catalyst- and additive-free conditions
    Zhou, Jiacheng
    Li, Meichao
    Li, Tianci
    Li, Chunmei
    Hu, Xinquan
    Jin, Liqun
    Sun, Nan
    Hu, Baoxiang
    Shen, Zhenlu
    TETRAHEDRON, 2021, 82