Transition-metal-free mono- or dinitration of protected anilines

被引：7
|
作者：
Dai Enrui [1 ]
Dong Yongrui [1 ]
Kong Rui [1 ]
Liu Guangzhang [1 ]
Dong Ying [2 ]
Wu Qiong [3 ]
Liang Deqiang [1 ,3 ]
Ma Yinhai [1 ]
机构：
[1] Kunming Univ, Sch Chem & Chem Engn, Kunming 650214, Yunnan, Peoples R China
[2] Shandong Normal Univ, Coll Chem Chem Engn & Mat Sci, Jinan, Peoples R China
[3] Yunnan Engn Technol Res Ctr Plast Films, Kunming 650214, Yunnan, Peoples R China
来源：
SYNTHETIC COMMUNICATIONS | 2020年 / 50卷 / 11期
基金：
中国国家自然科学基金;
关键词：
Amide-assisted strategy; anilides; C - H functionalization; divergent synthesis; radical reaction; C-H FUNCTIONALIZATION; N-ALLYL ANILINES; NITRATION; 8-AMINOQUINOLINES; ACTIVATION; ACID;
D O I：
10.1080/00397911.2020.1752730
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An amide-assisted arene nitration is presented, and both mono- and dinitration of protected anilines could be effected by using NaNO2 and NaNO3 as the mono- and bisnitrating agents, respectively. This divergent synthesis is transition-metal- and acid-free, and features a broad substrate scope, low cost, and ortho-para selectivity.
引用
收藏
页码：1687 / 1695
页数：9
相关论文
共 50 条
  • [1] Transition-Metal-Free Direct Arylation of Anilines
    Pirali, Tracey
    Zhang, Fengzhi
    Miller, Anna H.
    Head, Jenna L.
    McAusland, Donald
    Greaney, Michael F.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) : 1006 - 1009
  • [2] Transition-metal-free regioselective thiocyanation of phenols, anilines and heterocycles
    Mete, Trimbak B.
    Khopade, Tushar M.
    Bhat, Ramakrishna G.
    [J]. TETRAHEDRON LETTERS, 2017, 58 (05) : 415 - 418
  • [3] Transition-Metal-Free Regioselective Cross-Coupling: Controlled Synthesis of Mono- or Dithiolation Indolizines
    Li, Bin
    Chen, Zhiyu
    Cao, Hua
    Zhao, Hong
    [J]. ORGANIC LETTERS, 2018, 20 (11) : 3291 - 3295
  • [4] Aerobic, Transition-Metal-Free, Direct, and Regiospecific Mono-α-arylation of Ketones: Synthesis and Mechanism by DFT Calculations
    Xu, Qing-Long
    Gao, Hongyin
    Yousufuddin, Muhammed
    Ess, Daniel H.
    Kuerti, Laszlo
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (38) : 14048 - 14051
  • [5] Transition-Metal-Free Csp2-H Regioselective Thiocyanation of Free Anilines
    Dai, Peng
    Li, Chenxiao
    Li, Yufei
    Xia, Qing
    Zhang, Mingzhi
    Gu, Yu-Cheng
    Zhang, Wei-Hua
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (10) : 1585 - 1588
  • [6] Transition-Metal-Free Regioselective Thiocyanation of Triisopropylsilane (TIPS)-Protected Phenols
    Ju Guodong
    Zhou Guangyu
    Zhao Yingsheng
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (04) : 1327 - 1336
  • [7] Transition-metal-free C-H oxidative activation: persulfate-promoted selective benzylic mono- and difluorination
    Ma, Jing-jing
    Yi, Wen-bin
    Lu, Guo-ping
    Cai, Chun
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (10) : 2890 - 2894
  • [8] Transition-Metal-Free Approach for the Synthesis of 4-Aryl-quinolines from Alkynes and Anilines
    Phanindrudu, Mandalaparthi
    Wakade, Sandip Balasaheb
    Tiwari, Dipak Kumar
    Likhar, Pravin R.
    Tiwari, Dharmendra Kumar
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (16): : 9137 - 9143
  • [9] Carbazole and Triarylpyrrole Synthesis from Anilines and Cyclohexanones or Acetophenones under Transition-Metal-Free Condition
    Wu, Jun
    Chen, Xiangui
    Xie, Yanjun
    Guo, Yanjun
    Zhang, Qian
    Deng, Guo-Jun
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (11): : 5743 - 5750
  • [10] Regioselective and solvent-free arylation of β-nitrostyrenes with mono- and dialkyl anilines
    Ranjbari, Mohammad A.
    Tavakol, Hossein
    Manoukian, Meghmik
    [J]. RESEARCH ON CHEMICAL INTERMEDIATES, 2021, 47 (02) : 709 - 721
12345