Direct CH Bond Arylation of Indoles with Aryl Boronic Acids Catalyzed by Palladium Nanoparticles Encapsulated in Mesoporous Metal-Organic Framework

被引:81
|
作者
Huang, Yuanbiao [1 ]
Ma, Tao [1 ]
Huang, Ping [1 ]
Wu, Dongshuang [1 ]
Lin, Zujin [1 ]
Cao, Rong [1 ]
机构
[1] Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Fuzhou 350002, Peoples R China
关键词
aryl boronic acids; CH activation; indole; metal-organic frameworks; Pd nanoparticles; DIRECT C-2 ARYLATION; ORGANOMETALLIC CVD-PRECURSORS; HIGHLY-ACTIVE CATALYSTS; INCLUSION-COMPOUNDS; GOLD NANOPARTICLES; ROOM-TEMPERATURE; PD NANOPARTICLES; FUNCTIONALIZATION; OXIDATION; C3-ARYLATION;
D O I
10.1002/cctc.201200957
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
Highly dispersed Pd nanoparticles encapsulated in the mesoporous metal-organic framework MIL-101 demonstrated high activity and selectivity for the direct C2 arylation of various indoles with aryl boronic acids using O2 or 2,2,6,6-tetramethylpiperidine N-oxyradical as an external oxidant in acidic media under mild conditions. The green catalyst is easily recoverable and can be reused six times without leaching and loss of activity.
引用
收藏
页码:1877 / 1883
页数:7
相关论文
共 50 条
  • [31] Highly Efficient Synthesis of Arylpyrrole Derivatives via Rh(III)-Catalyzed Direct C-H Arylation with Aryl Boronic Acids
    Wang, Liang
    Li, Zhan
    Qu, Xing
    Peng, Wangming
    CHINESE JOURNAL OF CHEMISTRY, 2015, 33 (09) : 1015 - 1018
  • [32] Hydrogenation of Nitrobenzene Catalyzed by Metal-Organic Framework-Supported Ni Nanoparticles
    Jiang Jun
    Li Gang
    Kong Ling-Hao
    ACTA PHYSICO-CHIMICA SINICA, 2015, 31 (01) : 137 - 144
  • [33] Palladium(0)-catalyzed direct cross-coupling reaction of allyl alcohols with aryl- and vinyl-boronic acids
    Tsukamoto, H
    Sato, M
    Kondo, Y
    CHEMICAL COMMUNICATIONS, 2004, (10) : 1200 - 1201
  • [34] Palladium nanoparticles encapsulated inside the pores of a metal-organic framework as a highly active catalyst for carbon-carbon cross-coupling
    Shang, Ningzhao
    Gao, Shutao
    Zhou, Xin
    Feng, Cheng
    Wang, Zhi
    Wang, Chun
    RSC ADVANCES, 2014, 4 (97): : 54487 - 54493
  • [35] PALLADIUM-CATALYZED CROSS-COUPLING OF ARYL AND ALKENYL BORONIC ACIDS WITH ALKENES VIA OXIDATIVE ADDITION OF A CARBON-BORON BOND TO PALLADIUM(0)
    CHO, CS
    UEMURA, S
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 465 (1-2) : 85 - 92
  • [36] Size-Dependent Spin Crossover and Bond Flexibility in Metal-Organic Framework Nanoparticles
    Davenport, Audrey M.
    Marshall, Checkers R.
    Nishiguchi, Taichi
    Kadota, Kentaro
    Andreeva, Anastasia B.
    Horike, Satoshi
    Brozek, Carl K.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (34) : 23692 - 23698
  • [37] Room temperature synthesis of β-ketonitriles catalyzed by metal-organic framework supported Pd nanoparticles
    Li, Wen-Jing
    Wang, Zi-Qi
    Wang, Jun -Bo
    Wu, Rong
    Shi, Hong-Wei
    Liu, En-Xi
    Zhang, Mo
    Zhang, Zhan-Hui
    JOURNAL OF CATALYSIS, 2024, 430
  • [38] Highly Selective Acetylene Semihydrogenation Catalyzed by Cu Nanoparticles Supported in a Metal-Organic Framework
    Redfern, Louis R.
    Li, Zhanyong
    Zhang, Xuan
    Farha, Omar K.
    ACS APPLIED NANO MATERIALS, 2018, 1 (09): : 4413 - 4417
  • [39] Study on the Selective Hydrogenation of Quinoline Catalyzed by Composites of Metal-Organic Framework and Pt Nanoparticles
    Chen Junmin
    Cui Chengqian
    Liu Hanlin
    Li Guodong
    ACTA CHIMICA SINICA, 2022, 80 (04) : 467 - 475
  • [40] Friedel-Crafts Alkylation of Indoles with Nitroalkenes through Hydrogen-Bond-Donating Metal-Organic Framework
    Rao, Purna Chandra
    Mandal, Sukhendu
    CHEMCATCHEM, 2017, 9 (07) : 1172 - 1176