Copper-catalyzed, oxidative sp2 C-H cyanation: facile synthesis of aromatic carbonitriles

被引:8
|
作者
Liu, Jin-Qiang [1 ]
Hao, Bao-Yu [2 ,3 ]
Zou, Hao [2 ]
Zhang, Wei-Han [2 ]
Chen, Xin-Zhi [3 ]
机构
[1] Luoyang Normal Univ, Coll Chem & Chem Engn, Luoyang 471022, Peoples R China
[2] Hutchison MediPharma Ltd, Shanghai 201203, Peoples R China
[3] Zhejiang Univ, Dept Chem & Biol Engn, Hangzhou 310027, Zhejiang, Peoples R China
基金
高等学校博士学科点专项科研基金;
关键词
C-H activation; cyanation; copper catalyzed; aryl carbonitriles; NITRILES; CYANIDE; N; N-DIMETHYLFORMAMIDE; HETEROARENES; ALCOHOLS; INDOLES;
D O I
10.3998/ark.5550190.p008.682
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cu(OAc)(2)-catalyzed regioselective oxidative C-H cyanation of two different types of aromatics was described, providing facile access to functionalized heterocycles in good yields. Control experiments suggest the copper chelation-assisted oxidative C-H activation mechanism.
引用
收藏
页码:72 / 93
页数:22
相关论文
共 50 条
  • [41] Cu(TFA)2-Catalyzed Picolinamido-Directed C(sp2)-H Cyanation of Naphthalenes by Using Benzoyl Cyanide as a Cyano Source
    Song, He
    Liu, Xiaochong
    Wang, Chenglong
    Qiao, Jingyi
    Chu, Wenyi
    Sun, Zhizhong
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (11) : 1693 - 1698
  • [42] Copper-Catalyzed Aromatic C-H Bond Halogenation Using Lithium Halides as Halogenating Reagents
    Lu, Yongzhong
    Wang, Ruiping
    Qiao, Xixue
    Shen, Zengming
    SYNLETT, 2011, (07) : 1038 - 1042
  • [43] The facile construction of the phthalazin-1(2H)-one scaffold via copper-mediated C-H(sp2)/C-H(sp) coupling under mild conditions
    Zhu, Wei
    Wang, Bao
    Zhou, Shengbin
    Liu, Hong
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1624 - 1631
  • [44] Rhodium(III)-Catalyzed Direct Cyanation of Aromatic C-H Bond to Form 2-(Alkylamino)benzonitriles Using N-Nitroso As Directing Group
    Dong, Jiawei
    Wu, Zhongjie
    Liu, Zhengyi
    Liu, Ping
    Sun, Peipei
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24) : 12588 - 12593
  • [45] Cobalt(III)-Catalyzed [4+2] Annulation of Heterobicyclic Alkenes by sp2 C-H Activation
    Dey, Arnab
    Rathi, Anuja
    Volla, Chandra M. R.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (07) : 1362 - 1367
  • [46] Nickel-Catalyzed Decarboxylative Acylation of Heteroarenes by sp2 C-H Functionalization
    Yang, Ke
    Zhang, Cheng
    Wang, Peng
    Zhang, Yan
    Ge, Haibo
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (24) : 7241 - 7244
  • [47] Copper-Catalyzed Direct C-H Bond Oxidative Sulfonylation of β-Alkyl Cyanoalkenes with Sodium Sulfinates
    Jin, Junyi
    Zhou, Kaiyang
    Liu, Xinxiang
    Wang, Can
    Chen, Yunfeng
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (08)
  • [48] Cobalt-Catalyzed C(sp2)-H Alkoxylation of Aromatic and Olefinic Carboxamides
    Zhang, Lin-Bao
    Hao, Xin-Qi
    Zhang, Shou-Kun
    Liu, Zhan-Jiang
    Zheng, Xin-Xiang
    Gong, Jun-Fang
    Niu, Jun-Long
    Song, Mao-Ping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (01) : 272 - 275
  • [49] Copper-catalyzed monoselective C-H amination of ferrocenes with alkylamines
    Jia, Zhen-Sheng
    Yue, Qiang
    Li, Ya
    Xu, Xue-Tao
    Zhang, Kun
    Shi, Bing-Feng
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2021, 17 : 2488 - 2495
  • [50] Copper-catalyzed C-H/N-H annulation of enaminones and alkynyl esters for densely substituted pyrrole synthesis
    Fu, Leiqing
    Wan, Jie-Ping
    Zhou, Liyun
    Liu, Yunyun
    CHEMICAL COMMUNICATIONS, 2022, 58 (11) : 1808 - 1811