Nickel-catalyzed cyanation reaction of aryl/alkenyl halides with alkyl isocyanides

被引:12
|
作者
Zhang, Yanling [1 ]
Zhang, Zhiguo [1 ]
Hu, Yuanyuan [1 ]
Liu, Yunkui [1 ]
Jin, Hongwei [1 ]
Zhou, Bingwei [1 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H CYANATION; ARYL HALIDES; EFFICIENT CATALYSTS; COUPLING REACTIONS; TERMINAL ALKYNES; NITRILES; MILD; PD; COMPLEXES; BROMIDES;
D O I
10.1039/d2ob01240e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We herein describe a nickel-catalyzed cyanation reaction of aryl/alkenyl halides with alkyl isocyanides. Both aryl/alkenyl iodines and bromides were found to be competent electrophiles that reacted with alkyl isocyanides, affording nitrile compounds in moderate to good yields. A range of functional groups including halogens as well as hydroxyl, formyl, and acetamino groups were fairly compatible with the nickel catalysis. This protocol featured broad functional group tolerance, simple reaction conditions, and gram-scale synthesis.
引用
收藏
页码:8049 / 8053
页数:5
相关论文
共 50 条
  • [31] Nickel-catalyzed electrochemical carboxylation of unactivated aryl and alkyl halides with CO2
    Guo-Quan Sun
    Wei Zhang
    Li-Li Liao
    Li Li
    Zi-Hao Nie
    Jin-Gui Wu
    Zhen Zhang
    Da-Gang Yu
    Nature Communications, 12
  • [32] Nickel-catalyzed electrochemical homocoupling of alkenyl halides: Rates and mechanisms
    Cannes, C
    Labbe, E
    Durandetti, M
    Devaud, M
    Nedelec, JY
    JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1996, 412 (1-2): : 85 - 93
  • [33] Alkyl-aryl ketone synthesis via nickel-catalyzed reductive coupling of alkyl halides with aryl acids and anhydrides
    Jia, Xiao
    Zhang, Xinghua
    Qian, Qun
    Gong, Hegui
    CHEMICAL COMMUNICATIONS, 2015, 51 (51) : 10302 - 10305
  • [34] Nickel-Catalyzed Reductive Coupling of Aryl Halides with Secondary Alkyl Bromides and Allylic Acetate
    Wang, Shulin
    Qian, Qun
    Gong, Hegui
    ORGANIC LETTERS, 2012, 14 (13) : 3352 - 3355
  • [35] Nickel-Catalyzed Formal Aminocarbonylation of Unactivated Alkyl Iodides with Isocyanides
    Huang, Wenyi
    Wang, Yun
    Weng, Yangyang
    Shrestha, Mohini
    Qu, Jingping
    Chen, Yifeng
    ORGANIC LETTERS, 2020, 22 (08) : 3245 - 3250
  • [36] NICKEL-CATALYZED DISPLACEMENT-REACTIONS OF ARYL HALIDES
    CRAMER, R
    COULSON, DR
    JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (16): : 2267 - 2273
  • [37] Nickel-Catalyzed Cyanation of Aryl Triflates Using Acetonitrile as a Cyano Source
    Zhou K.
    Shen Z.
    Shanghai Jiaotong Daxue Xuebao/Journal of Shanghai Jiaotong University, 2023, 57 (10): : 1245 - 1249
  • [38] Nickel-Catalyzed Thiolation of Aryl Halides and Heteroaryl Halides through Electrochemistry
    Liu, Dong
    Ma, Hong-Xing
    Fang, Ping
    Mei, Tian-Sheng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (15) : 5033 - 5037
  • [39] Nickel-Catalyzed Cyanation of Unactivated Alkyl Sulfonates with Zn(CN)2
    Xia, Aiyou
    Lv, Peizhuo
    Xie, Xin
    Liu, Yuanhong
    ORGANIC LETTERS, 2020, 22 (20) : 7842 - 7847
  • [40] Decarboxylative photoredox/nickel-catalyzed conversion of aryl halides to aryl aminooxetanes
    Terrett, Jack
    Kolahdouzan, Kavoos
    Khalaf, Ryan
    Grandner, Jessica
    Chen, Yongsheng
    Huestis, Malcolm
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258