Nickel-catalyzed divergent formylation and carboxylation of aryl halides with isocyanides

被引:4
|
作者
Mao, Haoying [1 ]
Qian, Hongwei [1 ]
He, Zhichang [1 ]
Zhang, Zhiguo [1 ]
Jin, Hongwei [1 ]
Liu, Yunkui [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
Compendex;
D O I
10.1039/d3ob00327b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we describe a nickel-catalyzed divergent formylation and carboxylation reaction of aryl halides with isocyanides. A rich array of aromatic aldehydes and carboxylic acids can be, respectively, accessed in moderate to good yields. Some sensitive functional groups such as hydroxyl, iodine, cyano, and indolyl are fairly tolerant of nickel catalysis. In the carboxylation reactions, the combination of isocyanide and H2O is first employed as a promising carbonyl surrogate instead of gaseous CO and CO2.
引用
收藏
页码:3360 / 3364
页数:5
相关论文
共 50 条
  • [1] Nickel-catalyzed reductive formylation of aryl halides via formyl radical
    XiaoBo Liu
    RenMing Liu
    XiaoDi Bao
    HuaJian Xu
    Qi Zhang
    YuFeng Liang
    Chinese Chemical Letters, 2024, 35 (12) : 476 - 481
  • [2] Nickel-catalyzed cyanation reaction of aryl/alkenyl halides with alkyl isocyanides
    Zhang, Yanling
    Zhang, Zhiguo
    Hu, Yuanyuan
    Liu, Yunkui
    Jin, Hongwei
    Zhou, Bingwei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (41) : 8049 - 8053
  • [3] Nickel-catalyzed hydrodehalogenation of aryl halides
    Weidauer, Maik
    Irran, Elisabeth
    Someya, Chika I.
    Haberberger, Michael
    Enthaler, Stephan
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 729 : 53 - 59
  • [4] 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
  • [5] Nickel-catalyzed electrochemical carboxylation of unactivated aryl and alkyl halides with CO2
    Sun, Guo-Quan
    Zhang, Wei
    Liao, Li-Li
    Li, Li
    Nie, Zi-Hao
    Wu, Jin-Gui
    Zhang, Zhen
    Yu, Da-Gang
    NATURE COMMUNICATIONS, 2021, 12 (01)
  • [6] On the Feasibility of Nickel-Catalyzed Trifluoromethylation of Aryl Halides
    Jover, Jesus
    Miloserdov, Fedor M.
    Benet-Buchholz, Jordi
    Grushin, Vladimir V.
    Maseras, Feliu
    ORGANOMETALLICS, 2014, 33 (22) : 6531 - 6543
  • [7] Nickel-catalyzed aminocarbonylation of Aryl/Alkenyl/Allyl (pseudo) halides with isocyanides and H2O
    Li, Qiao
    Cai, Yun
    Jin, Hongwei
    Liu, Yunkui
    Zhou, Bingwei
    TETRAHEDRON LETTERS, 2020, 61 (51)
  • [8] NICKEL-CATALYZED DISPLACEMENT-REACTIONS OF ARYL HALIDES
    CRAMER, R
    COULSON, DR
    JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (16): : 2267 - 2273
  • [9] 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
  • [10] 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