Late-Stage C-H Nitration of Unactivated Arenes by Fe(NO3)3<middle dot>9H2O in Hexafluoroisopropanol

被引:9
作者
Zheng, Yuzhu [1 ]
Hu, Qi-Qi [1 ]
Huang, Qing [1 ]
Xie, Youwei [1 ]
机构
[1] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Hubei Key Lab Mat Chem & Serv Failure, Minist Educ,Hubei Key Lab Bioinorgan Chem & Mat Me, Wuhan 430074, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
NITRO-COMPOUNDS; HYDROARYLATION;
D O I
10.1021/acs.orglett.4c01006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Operationally simple and generally applicable arene nitration with cheap and easily accessible chemicals has been a long-sought transformation in the synthetic organic community. In this work, we realized this goal with nontoxic and inexpensive Fe(NO3)(3)<middle dot>9H(2)O as the nitro source and easily recyclable solvent hexafluoroisopropanol as the promotor via a network of hydrogen-bonding interactions. As a result of the relative mildness and high reliability of this protocol, late-stage nitration of various highly functionalized natural products and commercially available drugs was realized.
引用
收藏
页码:3316 / 3320
页数:5
相关论文
共 41 条
  • [1] Protein tyrosine nitration: A signaling mechanism conserved from yeast to man
    Bottari, Serge P.
    [J]. PROTEOMICS, 2015, 15 (2-3) : 185 - 187
  • [2] Facile access to nitroarenes and nitroheteroarenes using N-nitrosaccharin
    Calvo, Roxan
    Zhang, Kun
    Passera, Alessandro
    Katayev, Dmitry
    [J]. NATURE COMMUNICATIONS, 2019, 10 (1)
  • [3] Nitration of Pyrrolo[2,1-a]isoquinolines
    Chen, Xiao-Hui
    Ma, Dan-Dan
    Gao, Xin
    Li, Yun-Meng
    Jiang, Da-Bo
    Ma, Chao
    Cui, Hai-Lei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (07) : 4649 - 4661
  • [4] Total Synthesis of Anti-tuberculosis Natural Products Ilamycins E1 and F
    Cheng, Yingying
    Tang, Shoubin
    Guo, Yian
    Ye, Tao
    [J]. ORGANIC LETTERS, 2018, 20 (19) : 6166 - 6169
  • [5] Hydroarylation of Alkenes Using Anilines in Hexafluoroisopropanol
    Colomer, Ignacio
    [J]. ACS CATALYSIS, 2020, 10 (11): : 6023 - 6029
  • [7] Biochemistry of Peroxynitrite and Protein Tyrosine Nitration
    Ferrer-Sueta, Gerardo
    Campolo, Nicolas
    Trujillo, Madia
    Bartesaghi, Silvina
    Carballa, Sebastian
    Romero, Natalia
    Alvarez, Beatriz
    Radi, Rafael
    [J]. CHEMICAL REVIEWS, 2018, 118 (03) : 462 - +
  • [8] Reduction of Nitro Compounds Using 3d-Non-Noble Metal Catalysts
    Formenti, Dario
    Ferretti, Francesco
    Scharnagl, Florian Korbinian
    Beller, Matthias
    [J]. CHEMICAL REVIEWS, 2019, 119 (04) : 2611 - 2680
  • [9] Regio- and Chemoselective Mono- and Bisnitration of 8-Amino quinoline Amides with Fe(NO3)3•9H2O as Promoter and Nitro Source
    He, Yan
    Zhao, Ningning
    Qiu, Liqi
    Zhang, Xinying
    Fan, Xuesen
    [J]. ORGANIC LETTERS, 2016, 18 (23) : 6054 - 6057
  • [10] An Intermolecular Hydroarylation of Unactivated Arylcyclopropane via Re2O7/HFIP-Mediated Ring Opening
    Hu, Liqun
    Xiang, Yao
    Lan, Xiao-Bing
    Xie, Youwei
    [J]. ORGANIC LETTERS, 2024, 26 (10) : 2085 - 2090