Rhodium(III)-catalyzed aromatic C-H cyanation with dimethylmalononitrile as a cyanating agent

被引：21
作者：
Li, He [1 ]
Zhang, Sheng [1 ]
Yu, Xiaoqiang [1 ]
Feng, Xiujuan [1 ]
Yamamoto, Yoshinori [1 ,3 ,4 ]
Bao, Ming [1 ,2 ]
机构：
[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116023, Peoples R China
[2] Dalian Univ Technol, Sch Petr & Chem Engn, Panjin 124221, Peoples R China
[3] Tohoku Univ, WPI Adv Inst Mat Res, Sendai, Miyagi 9808577, Japan
[4] Ritsumeikan Univ, Res Org Sci & Technol, Kusatsu, Shiga 5258577, Japan
来源：
CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 09期
基金：
中国博士后科学基金; 中国国家自然科学基金;
关键词：
RHODIUM-CATALYZED CYANATION; LITHIUM REAGENTS; ARENES; BOND; TRANSNITRILATION; CHLORIDES; NITRILES; GRIGNARD; HALIDES; CARBON;
D O I：
10.1039/c8cc08930b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A rhodium-catalyzed aromatic C-H bond direct cyanation with safe, bench-stable, and commercially available dimethylmalononitrile as the cyanating agent has been successfully developed by using copper oxide as a promotor. Pyridine, quinoline, pyrimidine and pyrazole were used as the directing group in this type of C-H bond direct cyanation reaction.
引用
收藏
页码：1209 / 1212
页数：4
相关论文
共 50 条
  • [1] α-Iminonitrile: a new cyanating agent for the palladium catalyzed C-H cyanation of arenes
    Chen, Zhen-Bang
    Zhang, Fang-Ling
    Yuan, Qing
    Chen, Hai-Fang
    Zhu, Yong-Ming
    Shen, Jing-Kang
    RSC ADVANCES, 2016, 6 (69): : 64234 - 64238
  • [2] Rhodium Catalyzed Cyanation of Chelation Assisted C-H Bonds
    Chaitanya, Manthena
    Yadagiri, Dongari
    Anbarasan, Pazhamalai
    ORGANIC LETTERS, 2013, 15 (19) : 4960 - 4963
  • [3] Cobalt-Catalyzed C-H Cyanation of (Hetero)arenes and 6-Arylpurines with N-Cyanosuccinimide as a New Cyanating Agent
    Pawar, Amit B.
    Chang, Sukbok
    ORGANIC LETTERS, 2015, 17 (03) : 660 - 663
  • [4] Rhodium(III)-Catalyzed Selective C-H Cyanation of Indolines and Indoles with an Easily Accessible Cyano Source
    Mishra, Neeraj Kumar
    Jeong, Taejoo
    Sharma, Satyasheel
    Shin, Youngmi
    Han, Sangil
    Park, Jihye
    Oh, Joa Sub
    Kwak, Jong Hwan
    Jung, Young Hoon
    Kim, In Su
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (06) : 1293 - 1298
  • [5] Copper-catalyzed cyanation of heterocycle C-H bonds with ethyl(ethoxymethylene) cyanoacetate as a cyanating agent and its mechanism
    Li, Ze-Lin
    Sun, Kang-Kang
    Cai, Chun
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (11): : 1848 - 1853
  • [6] Nickel-Catalyzed Selective C-H Cyanation via Aromatic Thianthrenium Salts
    Zhang, Guofu
    Luo, Zijin
    Guan, Chenfei
    Zhang, Xianghao
    Ding, Chengrong
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13) : 9249 - 9256
  • [7] Copper-mediated C-H cyanation of (hetero) arenes with ethyl (ethoxymethylene) cyanoacetate as a cyanating agent
    Qi, Chaorong
    Hu, Xiaohan
    Jiang, Huanfeng
    CHEMICAL COMMUNICATIONS, 2017, 53 (57) : 7994 - 7997
  • [8] Rhodium-Catalyzed Direct C-H Bond Cyanation in Ionic Liquids
    Lv, Songyang
    Li, Yaling
    Yao, Tian
    Yu, Xinling
    Zhang, Chen
    Hai, Li
    Wu, Yong
    ORGANIC LETTERS, 2018, 20 (16) : 4994 - 4997
  • [9] 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
  • [10] Rhodium(III)-Catalyzed C-H Olefination of Aromatic/Vinyl Acids with Unactivated Olefins at Room Temperature
    Jambu, Subramanian
    Jeganmohan, Masilamani
    ORGANIC LETTERS, 2020, 22 (13) : 5057 - 5062
12345