Synthesis of functionalized benzimidazoles via oxidative tandem quartic C-H aminations and cleavage of C-N and C-C bonds

被引:4
|
作者
Liang, Taoyuan [1 ]
Zhao, He [1 ]
Gong, Lingzhen [1 ]
Jiang, Huanfeng [1 ]
Zhang, Min [1 ,2 ]
机构
[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Wushan Rd 381, Guangzhou 510641, Peoples R China
[2] Qingyuan Huayuan Inst Sci & Technol Collaborat In, Qingyuan 511500, Peoples R China
基金
中国国家自然科学基金;
关键词
COPPER-CATALYZED SYNTHESIS;
D O I
10.1039/d1cc05521f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Via aerobic copper-catalyzed tandem quartic C-H aminations, we herein present an unprecedented approach for the synthesis of functionalized benzimidazoles from aniline derivatives and 2-substituted cyclic amines. The cyclic amines act as the C=N building blocks and are involved in the annulation reaction by cleavage of inert alpha-C-N and beta-C-C bonds. The synthetic protocol features high selectivity, no need for specific aminating agents, mild conditions, and the use of a naturally abundant [Cu]/O-2 catalyst system.
引用
收藏
页码:12976 / 12979
页数:4
相关论文
共 50 条
  • [1] Synthesis of C-C and C-N bonds via oxidative C-H activation
    DeBoef, Brenton
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [2] Synthesis of C-C and C-N bonds via oxidative C-H activation
    DeBoef, Brenton
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [3] Synthesis of C-C and C-N bonds via oxidative C-H functionalization
    DeBoef, Brenton
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [4] Oxidative cleavage of the C-H, C-C, C-O bonds by transition metal atoms
    Wang, Jiaqi
    Wilson, Angela K.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [5] Consequent Construction of C-C and C-N Bonds via Palladium-Catalyzed Dual C-H Activation: Synthesis of Benzo[c]cinnoline Derivatives
    Li, Hongsheng
    Zhao, Junhao
    Yi, Songjian
    Hu, Kongzhen
    Feng, Pengju
    [J]. ORGANOMETALLICS, 2021, 40 (07) : 880 - 889
  • [6] Nitrogenation of Amides via C-C and C-N Bond Cleavage
    Zhu, Ming -Hui
    Cheng, Zengrui
    Wei, Jialiang
    Tan, Hui
    Jiao, Ning
    [J]. CCS CHEMISTRY, 2023, 5 (05): : 1061 - 1068
  • [7] C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation
    Song, Guoyong
    Wang, Fen
    Li, Xingwei
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) : 3651 - 3678
  • [8] Converting C-H to C-C bonds: Synthesis of veratramine
    Taber, Douglass F.
    Berry, James F.
    DeMatteo, Peter W.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [9] Amide-Directed Tandem C-C/C-N Bond Formation through C-H Activation
    Zhu, Chen
    Wang, Rui
    Falck, John R.
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (07) : 1502 - 1514
  • [10] Oxidative formation of C-C bonds directly from C-H/C-H bonds with dioxygen as terminal oxidant
    Li, Chao-Jun
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248