Transition-metal-free direct nucleophilic substitution of carboranyllithium and 2-halopyridines

被引：15
|
作者：
Lu J.-Y. [1 ,2 ]
Zhao B. [2 ]
Du Y. [2 ]
Yang J. [1 ]
Lu J. [1 ,2 ]
机构：
[1] Laboratory of Green Catalysis and Reaction Engineering of Haikou, Hainan Provincial Fine Chemical Engineering Research Center, School of Sciences, Hainan University, Haikou
[2] State Key Laboratory of Fluorine and Nitrogen Chemicals, Xi'An Modern Chemistry Research Institute, Xi'an Shaanxi
来源：
Organic and Biomolecular Chemistry | 2019年 / 17卷 / 32期
基金：
中国国家自然科学基金;
关键词：
Transition metals;
D O I：
10.1039/c9ob00978g
中图分类号：
学科分类号：
摘要：
A practical and efficient C(cage)-heteroarylation of carborane is presented, via direct nucleophilic substitution of carboranyllithium with 2-halopyridines. This reaction does not need the aid of any transition metal and utilizes readily available carboranyllithium nucleophiles, thereby avoiding transmetalation of carboranyllithium. The process exhibits a broad scope, and a vast array of 2-halopyridines have proven to be suitable substrates. The method serves as a complement to C(cage)-arylation reactions and may find wide applications in materials science and medicinal and coordination chemistry. © 2019 The Royal Society of Chemistry.
引用
收藏
页码：7438 / 7441
页数：3
相关论文
共 50 条
  • [21] Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions
    Fier, Patrick S.
    Maloney, Kevin M.
    ORGANIC LETTERS, 2016, 18 (09) : 2244 - 2247
  • [22] Transition-Metal-Free Direct Trifluoromethylation and Perfluoroalkylation of Imidazopyridines under Mild Conditions
    Han, Shuaijun
    Gao, Xianying
    Wu, Qingsong
    Li, Jingya
    Zou, Dapeng
    Wu, Yangjie
    Wu, Yusheng
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (07) : 1559 - 1563
  • [23] Chemo- and regioselective nucleophilic hydrofunctionalization of unactivated aliphatic alkenes under transition-metal-free catalysts
    Zhan, Ying
    Zhao, Yao
    Du, Qiang
    Rui, Jiacheng
    Chen, Rizhi
    Zheng, Xintao
    Wu, Xiaojin
    GREEN CHEMISTRY, 2021, 23 (09) : 3250 - 3255
  • [24] Transition-Metal-Free Defluorosilylation of Fluoroalkenes with Silylboronates
    Gao, Pan
    Wang, Guoqiang
    Xi, Longlong
    Wang, Minyan
    Li, Shuhua
    Shi, Zhuangzhi
    CHINESE JOURNAL OF CHEMISTRY, 2019, 37 (10) : 1009 - 1014
  • [25] Transition-Metal-Free Deconstructive Lactamization of Piperidines
    Romero-Ibanez, Julio
    Cruz-Gregorio, Silvano
    Sandoval-Lira, Jacinto
    Hernandez-Perez, Julio M.
    Quintero, Leticia
    Sartillo-Piscil, Fernando
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (26) : 8867 - 8871
  • [26] A Transition-Metal-Free Synthesis of Fluorinated Naphthols
    Hammann, Jeffrey M.
    Unzner, Teresa A.
    Magauer, Thomas
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (22) : 6733 - 6738
  • [27] Transition-metal-free homocoupling of organomagnesium compounds
    Krasovskiy, Arkady
    Tishkov, Alexander
    del Amo, Vicente
    Mayr, Herbert
    Knochel, Paul
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (30) : 5010 - 5014
  • [28] Transition-Metal-Free Thioboration of Terminal Alkynes
    Matsuyama, Taro
    Ishida, Hiroshi
    Wang, Chao
    Miyamoto, Kazunori
    Nakajima, Masaya
    Toriumi, Naoyuki
    Nagashima, Yuki
    Uchiyama, Masanobu
    JACS AU, 2024,
  • [29] Transition-Metal-Free Radical Hydrotrifluoromethylation of Alkynes
    Matcha, Kiran
    Antonchick, Andrey P.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (2-3) : 309 - 312
  • [30] Transition-Metal-Free Reductive Hydroxymethylation of Isoquinolines
    Reeves, Benjamin M.
    Hepburn, Hamish B.
    Grozavu, Alexandru
    Lindsay-Scott, Peter J.
    Donohoe, Timothy J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (44) : 15697 - 15701
12345