MnO2@Fe3O4 Magnetic Nanoparticles as Efficient and Recyclable Heterogeneous Catalyst for Benzylic sp3 C-H Oxidation

被引:9
|
作者
Pandey, Akanksha M. [1 ]
Agalave, Sandip G. [1 ]
Vinod, Chathakudath P. [2 ]
Gnanaprakasam, Boopathy [1 ]
机构
[1] Indian Inst Sci Educ & Res, Dept Chem, Pune 411008, Maharashtra, India
[2] CSIR NCL Catalysis & Inorgan Chem Div, Pune, Maharashtra, India
关键词
Benzylic sp(3) C-H Oxidation; Carbonyl Compounds; Continuous flow; Heterogeneous Catalysis; Magnetic Nanoparticles; tert-Butyl Hydroperoxide; TERT-BUTYL HYDROPEROXIDE; SELECTIVE OXIDATION; MANGANESE-DIOXIDE; AEROBIC OXIDATION; SATURATED-HYDROCARBONS; CARBONYL-COMPOUNDS; ALKYLARENES; ALKANES; BONDS; MILD;
D O I
10.1002/asia.201900810
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, we report a highly chemoselective and efficient heterogeneous MnO2@Fe3O4 MNP catalyst for the oxidation of benzylic sp(3) C-H group of ethers using TBHP as a green oxidant to afford ester derivatives in high yield under batch/continuous flow module. This catalyst was also effective for the benzylic sp(3) C-H group of methylene derivatives to furnish the ketone in high yield which can be easily integrated into continuous flow condition for scale up. The catalyst is fully characterized by spectroscopic techniques and it was found that 0.424 % MnO2@Fe3O4 catalyzes the reaction; the magnetic nanoparticles of this catalyst could be easily recovered from the reaction mixture. The recovered catalyst was recycled for twelve cycles without any loss of the catalytic activity. The advantages of MnO2@Fe3O4 MNP are its catalytic activity, easy preparation, recovery, and recyclability, gram scale synthesis with a TOF of up to 14.93 h(-1) and low metal leaching during the reaction.
引用
收藏
页码:3414 / 3423
页数:10
相关论文
共 50 条
  • [41] Stereoretentive H/D Exchange via an Electroactivated Heterogeneous Catalyst at sp3 C-H Sites Bearing Amines or Alcohols
    Bhatia, Souful
    Spahlinger, Greg
    Boukhumseen, Nehal
    Boll, Quentin
    Li, Zhenglong
    Jackson, James E.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (24) : 4230 - 4235
  • [42] Distinctive size effects of Pt nanoparticles immobilized on Fe3O4@PPy used as an efficient recyclable catalyst for benzylic alcohol aerobic oxidation and hydrogenation reduction of nitroaromatics
    Long, Yu
    Yuan, Bing
    Niu, Jianrui
    Tong, Xin
    Ma, Jiantai
    [J]. NEW JOURNAL OF CHEMISTRY, 2015, 39 (02) : 1179 - 1185
  • [43] Catalytic Intermolecular C(sp3)-H Amination: Selective Functionalization of Tertiary C-H Bonds vs Activated Benzylic C-H Bonds
    Brunard, Erwan
    Boquet, Vincent
    Van Elslande, Elsa
    Saget, Tanguy
    Dauban, Philippe
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (17) : 6407 - 6412
  • [44] Solvent-free aerobic photocatalytic oxidation of C(sp3)-H and C(sp3)-OH to C=O bonds
    Jiang, Xulu
    Wang, Weitao
    Wang, Huan
    He, Zhen-Hong
    Yang, Yang
    Wang, Kuan
    Liu, Zhao-Tie
    Han, Buxing
    [J]. GREEN CHEMISTRY, 2024, 26 (08) : 4552 - 4562
  • [45] Active sp3 C-H Bond Oxidation Initiated sp3-sp2 Consecutive C-H Functionalization of N-Arylglycine Amides: Construction of Isatins
    Ji, Honghe
    Zhu, Yingzu
    Shao, Yu
    Liu, Jing
    Yuan, Yu
    Jia, Xiaodong
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (18): : 9859 - 9865
  • [46] Ruthenium(0)-Catalyzed sp3 C-H Bond Arylation of Benzylic Amines Using Arylboronates
    Dastbaravardeh, Navid
    Schnuerch, Michael
    Mihovilovic, Marko D.
    [J]. ORGANIC LETTERS, 2012, 14 (07) : 1930 - 1933
  • [47] Pd(0)-catalyzed benzylic arylation-oxidation of 4-methylquinazolines via sp3 C-H activation under air conditions
    Zhao, Dan
    Zhu, Min-Xue
    Wang, Yue
    Shen, Qi
    Li, Jian-Xin
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (37) : 6246 - 6249
  • [48] Fe3O4@SiO2/EDAC-Pd(0) as a novel and efficient inorganic/organic magnetic composite: sustainable catalyst for the benzylic C-H bond oxidation and reductive amination under mild conditions
    Bhardwaj, Madhvi
    Sharma, Harsha
    Paul, Satya
    Clark, James H.
    [J]. NEW JOURNAL OF CHEMISTRY, 2016, 40 (06) : 4952 - 4961
  • [49] AIBN-initiated direct thiocyanation of benzylic sp3 C-H with N-thiocyanatosaccharin
    Wu, Di
    Duan, Yongjie
    Liang, Kun
    Yin, Hongquan
    Chen, Fu-Xue
    [J]. CHEMICAL COMMUNICATIONS, 2021, 57 (77) : 9938 - 9941
  • [50] Fe3O4 magnetic nanoparticles (MNPs) as an efficient catalyst for allylic oxidation of chromenes to coumarins with TBHP
    Maurya, Rohit Kumar
    Dey, Ashutosh
    Niharika, Avanigadda Madhu
    Kumar, Vikash
    Burra, Amarender Goud
    Khatravath, Dr. Mahender
    [J]. Journal of Molecular Structure, 2025, 1322