Rh(III)-catalyzed direct cross-dehydrogenative coupling of aromatic nitriles with heteroarenes: Rapid access to biheteroaryl-2-carbonitriles

被引:21
作者
Xu, Huibei [1 ]
Zhu, Yanying [1 ]
Chai, Xinyue [1 ]
Yang, Jiahui [1 ]
Dong, Lin [1 ]
机构
[1] Sichuan Univ, Sichuan Res Ctr Drug Precis Ind Technol, West China Sch Pharm, Key Lab Drug Targeting & Drug Delivery Syst Educ M, Chengdu 610041, Peoples R China
来源
GREEN SYNTHESIS AND CATALYSIS | 2020年 / 1卷 / 02期
基金
中国国家自然科学基金;
关键词
Rh(III)-catalysis; Cross-dehydrogenative coupling; C-H activation; Heteroarylation; Biphenyl-2-carbonitriles; H BOND ACTIVATION; CATALYZED C-H; ANNULATION CASCADE; DIRECT CYANATION; CYANO; INDOLES; RHODIUM; ARENES; FUNCTIONALIZATION; ARYLNITRILES;
D O I
10.1016/j.gresc.2020.09.001
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Transition-metal-catalyzed direct C-H/C-H cross-coupling reactions as efficient and atom-economical approaches have been widely used to build up complex heterocyclic compounds. However, the strategy for preparation of biphenyl-2-carbonitriles has not been well established. Herein, we described the first cyanogen directed Rh(III)catalyzed CDC reaction of aromatic nitriles with heteroarenes. Various biphenyl-2-carbonitrilederivatives were obtained with broad functional group compatibility.
引用
收藏
页码:167 / 170
页数:4
相关论文
共 67 条
  • [1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations
    Ackermann, Lutz
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) : 281 - 295
  • [2] Recent developments and perspectives in palladium-catalyzed cyanation of aryl halides: synthesis of benzonitriles
    Anbarasan, Pazhamalai
    Schareina, Thomas
    Beller, Matthias
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5049 - 5067
  • [3] Remote para-C-H Functionalization of Arenes by a D-Shaped Biphenyl Template-Based Assembly
    Bag, Sukdev
    Patra, Tuhin
    Modak, Atanu
    Deb, Arghya
    Maity, Soham
    Dutta, Uttam
    Dey, Aniruddha
    Kancherla, Rajesh
    Maji, Arun
    Hazra, Avijit
    Bera, Milan
    Maiti, Debabrata
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (37) : 11888 - 11891
  • [4] Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups
    Chen, Zhengkai
    Wang, Binjie
    Zhang, Jitan
    Yu, Wenlong
    Liu, Zhanxiang
    Zhang, Yuhong
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09): : 1107 - 1295
  • [5] Nickel Catalysis Enables Oxidative C(sp2)-H/C(sp2)-H Cross-Coupling Reactions between Two Heteroarenes
    Cheng, Yangyang
    Wu, Yimin
    Tan, Guangyin
    You, Jingsong
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (40) : 12275 - 12279
  • [6] Pd(II)-Catalyzed ortho- or meta-C-H Olefination of Phenol Derivatives
    Dai, Hui-Xiong
    Li, Gang
    Zhang, Xing-Guo
    Stepan, Antonia F.
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (20) : 7567 - 7571
  • [7] COMPLEXES OF THE PLATINUM METALS CONTAINING WEAK DONOR LIGANDS
    DAVIES, JA
    HARTLEY, FR
    [J]. CHEMICAL REVIEWS, 1981, 81 (01) : 79 - 90
  • [8] Palladium catalysed meta-C-H functionalization reactions
    Dey, Aniruddha
    Agasti, Soumitra
    Maiti, Debabrata
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (24) : 5440 - 5453
  • [9] N,N-Dimethylformamide: A Multipurpose Building Block
    Ding, Shengtao
    Jiao, Ning
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (37) : 9226 - 9237
  • [10] Direct Transformation of N,N-Dimethylformamide to -CN: Pd-Catalyzed Cyanation of Heteroarenes via C-H Functionalization
    Ding, Shengtao
    Jiao, Ning
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (32) : 12374 - 12377