Ag1Pd1 Nanoparticles-Reduced Graphene Oxide as a Highly Efficient and Recyclable Catalyst for Direct Aryl C-H Olefination

被引:21
作者
Hu, Qiyan [1 ]
Liu, Xiaowang [1 ]
Wang, Guoliang [1 ]
Wang, Feifan [1 ]
Li, Qian [1 ]
Zhang, Wu [1 ]
机构
[1] Anhui Normal Univ, Coll Chem & Mat Sci, Anhui Lab Mol Based Mat, Minist Educ,Key Lab Funct Mol Solids, 1 Beijing East Rd, Wuhu 241000, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
Ag1Pd1; nanoparticles; C-H olefination; heterogeneous catalysis; recyclable catalysts; reduced graphene oxide; CROSS-COUPLING REACTIONS; BOND FUNCTIONALIZATION; BIMETALLIC NANOPARTICLES; PALLADIUM NANOPARTICLES; ALLOY NANOPARTICLES; ALIPHATIC ALKENES; PD NANOPARTICLES; ACTIVATION; OXIDATION; AMINATION;
D O I
10.1002/chem.201704056
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The efficient and selective palladium-catalyzed activation of C-H bonds is of great importance for the construction of diverse bioactive molecules. Despite significant progress, the inability to recycle palladium catalysts and the need for additives impedes the practical applications of these reactions. Ag1Pd1 nanoparticles-reduced graphene oxide (Ag1Pd1-rGO) was used as highly efficient and recyclable catalyst for the chelation-assisted ortho C-H bond olefination of amides with acrylates in good yields with a broad substrate scope. The catalyst can be recovered and reused at least 5 times without losing activity. A synergistic effect between the Ag and Pd atoms on the catalytic activity was found, and a plausible mechanism for the AgPd-rGO catalyzed C-H olefination is proposed. These findings suggest that the search for such Pd-based bimetallic alloy nanoparticles is a new method towards the development of superior recyclable catalysts for direct aryl C-H functionalization under mild conditions.
引用
收藏
页码:17659 / 17662
页数:4
相关论文
共 54 条
  • [1] Palladium Nanoparticle-Catalyzed Direct Ethynylation of Aliphatic Carboxylic Acid Derivatives via C(sp3)-H Bond Functionalization
    Al-Amin, Mohammad
    Arisawa, Mitsuhiro
    Shuto, Satoshi
    Ano, Yusuke
    Tobisu, Mamoru
    Chatani, Naoto
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) : 1631 - 1637
  • [2] [Anonymous], 2016, ANGEW CHEM
  • [3] Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
  • [4] Efficient, Selective, and Recyclable Palladium Catalysts in Carbon-Carbon Coupling Reactions
    Arpad Molnar
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 2251 - 2320
  • [5] Role of Lewis acid additives in a palladium catalyzed directed C-H functionalization reaction of benzohydroxamic acid to isoxazolone
    Athira, C.
    Sunoj, Raghavan B.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (01) : 246 - 255
  • [6] Pd nanoparticles for C-C coupling reactions
    Balanta, Angelica
    Godard, Cyril
    Claver, Carmen
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 4973 - 4985
  • [7] Replacing Pd(OAc)2 with supported palladium nanoparticles in ortho-directed CDC reactions of alkylbenzenes
    Bao, Yong-Sheng
    Zhang, Dongling
    Jia, Meilin
    Bao Zhaorigetu
    [J]. GREEN CHEMISTRY, 2016, 18 (07) : 2072 - 2077
  • [8] Fast synthesis of Ag-Pd@reduced graphene oxide bimetallic nanoparticles and their applications as carbon-carbon coupling catalysts
    Chen, Mingxi
    Zhang, Zhe
    Li, Lingzhi
    Liu, Yu
    Wang, Wei
    Gao, Jianping
    [J]. RSC ADVANCES, 2014, 4 (58): : 30914 - 30922
  • [9] Chen X., 2009, ANGEW CHEM, V121, P5196
  • [10] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality
    Chen, Xiao
    Engle, Keary M.
    Wang, Dong-Hui
    Yu, Jin-Quan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) : 5094 - 5115