Recent Developments in the Direct Methylation of Electron-Deficient N-Heteroarenes

被引:20
作者
Kim, Junghoon [1 ]
Cho, Seung Hwan [1 ]
机构
[1] Pohang Univ Sci & Technol POSTECH, Dept Chem, Pohang 790784, South Korea
基金
新加坡国家研究基金会;
关键词
N-heteroarenes; methylation; radical reaction; catalysis; transition-metal-free; H BOND FUNCTIONALIZATION; DIRECT ALKYLATION; SELECTIVE ALKYLATION; OXIDES; PYRIDINE; ARYLATION; REAGENTS; HETEROCYCLES; ACTIVATION; SULFOXIDES;
D O I
10.1055/s-0036-1588073
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The direct introduction of methyl groups into electron-deficient N-heteroarenes has recently emerged as an efficient and promising strategy to afford methylated N-heteroarenes, which are important motifs in a variety of pharmaceuticals and biologically active molecules. Herein, three general state-of-the-art approaches including radical-mediated, transition-metal-catalyzed, or transition-metal-free direct C-H methylations of electron-deficient N-heteroarenes are highlighted.
引用
收藏
页码:2525 / 2529
页数:5
相关论文
共 50 条
  • [41] Synthesis of polyfluoroalkylphosphorylated dihydroquinolines and dihydroisoquinolines decorated with N-acylethenyl substituents by the reaction of bis(polyfluoroalkyl)phosphonates with electron-deficient acetylenes and quinolines
    Volkov, Pavel A.
    Khrapova, Kseniya O.
    Telezhkin, Anton A.
    Albanov, Alexander I.
    Trofimov, Boris A.
    JOURNAL OF FLUORINE CHEMISTRY, 2023, 270
  • [42] Beyond simple hetero Diels-Alder cycloadditions. A new type of element-ligand cooperativity at N, C,N-coordinated arsinidene and stibinidene centres in the reaction with an electron-deficient alkyne
    Zechovsky, Jan
    Kremlacek, Vit
    Erben, Milan
    Hejda, Martin
    Rychagova, Elena
    Jambor, Roman
    Ruzicka, Ales
    Ketkov, Sergey
    Dostal, Libor
    DALTON TRANSACTIONS, 2022, 51 (41) : 15933 - 15945
  • [43] Computational and experimental studies on copper-mediated selective cascade C-H/N-H annulation of electron-deficient acrylamide with arynes
    Chen, Chao
    Hao, Yu
    Zhang, Ting-Yu
    Pan, Jin-Long
    Ding, Jun
    Xiang, Heng-Ye
    Wang, Man
    Ding, Tong-Mei
    Duan, Abing
    Zhang, Shu-Yu
    CHEMICAL COMMUNICATIONS, 2019, 55 (06) : 755 - 758
  • [44] Nickel-Catalyzed Reaction of Arylzinc Reagents with N-Aromatic Heterocycles: A Straightforward Approach to C-H Bond Arylation of Electron-Deficient Heteroaromatic Compounds
    Tobisu, Mamoru
    Hyodo, Isao
    Chatani, Naoto
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (34) : 12070 - +
  • [45] Pd-Catalyzed Redox-Neutral C-N Coupling Reaction of Iminoquinones with Electron-Deficient Alkenes without External Oxidants: Access of Tertiary (E)-Enamines and Application to the Synthesis of Indoles and Quinolin-4-ones
    Jillella, Raveendra
    Raju, Selvam
    Hsiao, Huan-Chang
    Hsu, Day-Shin
    Chuang, Shih-Ching
    ORGANIC LETTERS, 2020, 22 (16) : 6252 - 6256
  • [46] SERS Spectroscopy and DFT Studies of Thionine and its Derivatives Adsorbed on Silver Colloids: Which N Atom is Used for Coordination of a Phenothiazine-Based Natural Dye to Electron-Deficient Metal Surface?
    Yu, Malg-Eum
    Cheong, Byeong-Seo
    Cho, Han-Gook
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2017, 38 (08) : 928 - 934
  • [47] Revealing the activity of inert Zn-based ZIF-L/aerogel composites in Fenton-like catalysis: Electron-deficient N (-C=N-C) triggering 1O2 evolution
    Peng, Haihao
    Xu, Zhengyong
    Yang, Zhaohui
    Tong, Jing
    Xiang, Yinping
    Xiong, Weiping
    CHEMICAL ENGINEERING JOURNAL, 2024, 487
  • [48] Palladium-catalyzed C-N bond formation via direct C-H bond functionalization. Recent developments in heterocyclic synthesis
    Beccalli, Egle M.
    Broggini, Gianluigi
    Fasana, Andrea
    Rigamonti, Micol
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (01) : 277 - 295
  • [49] [2+2+2] Annulation of N-(1-Naphthyl)acetamide with Two Alkynoates via Cleavage of Adjacent C-H and C-N Bonds Catalyzed by an Electron-Deficient Rhodium(III) Complex
    Terasawa, Jyunichi
    Shibata, Yu
    Fukui, Miho
    Tanaka, Ken
    MOLECULES, 2018, 23 (12):
  • [50] Reaction of electron-deficient 6-methoxyquinolinate-substituted cluster [Os3(CO)9{μ3-η1, κ1-C9H5N(6-OMe)}(μ-H)] with PPh3: Thermally induced ligand isomerization, decarbonylation and orthometallation
    Begum, Shahin A.
    Chowdhury, Arshad H.
    Ghosh, Shishir
    Tocher, Derek A.
    Rosenberg, Edward
    Hardcastle, Kenneth I.
    Kabir, Shariff E.
    INORGANICA CHIMICA ACTA, 2018, 478 : 25 - 31