Lewis Acid and Fluoroalcohol Mediated Nucleophilic Addition to the C2 Position of Indoles

被引:41
|
作者
Morimoto, Naoki [1 ]
Morioku, Kumika [2 ]
Suzuk, Hideyuki [3 ]
Takeuchi, Yasuo [1 ]
Nishina, Yuta [3 ,4 ]
机构
[1] Okayama Univ, Grad Sch Med Dent & Pharmaceut Sci, Div Pharmaceut Sci, Kita Ku, Okayama 7008530, Japan
[2] Okayama Univ, Fac Engn, Dept Appl Chem & Biotechnol, Kita Ku, Okayama 7008530, Japan
[3] Okayama Univ, Res Core Interdisciplinary Sci, Kita Ku, Okayama 7008530, Japan
[4] Japan Sci & Technol Agcy, Precursory Res Embryon Sci & Technol, 4-1-8 Honcho, Kawaguchi, Saitama 3320012, Japan
关键词
N-ACETYL INDOLES; HETEROCYCLIC CHEMISTRY; AROMATIC HETEROCYCLES; BUILDING-BLOCKS; DERIVATIVES; BENZOFUROINDOLINES; FUNCTIONALIZATION; STEREOCHEMISTRY; HYDROARYLATION; CONSTRUCTION;
D O I
10.1021/acs.orglett.6b00629
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Indole readily undergoes nucleophilic substitution at the C3 site, and many indole derivatives have been functionalized using this property. Indole also forms indolium, which allows electrophilic addition in acidic conditions, but current examples have been limited to intramolecular reactions. C2 site-selective nucleophilic addition to indole derivatives using fluoroalcohol and a Lewis acid was developed.
引用
收藏
页码:2020 / 2023
页数:4
相关论文
共 50 条
  • [1] Selectivity in the Addition of Electron-Deficient Radicals to the C2 Position of Indoles
    Li, Yi
    Vaz, Roy J.
    Olson, Steven H.
    Munson, Mark
    Paras, Nick A.
    Conrad, Jay
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (36) : 5828 - 5832
  • [2] Lewis Acid Mediated Addition of Indoles and Alcohols to Tetronic Acid and Tetramic Acids
    Mejia, Fernando Banales
    Lafferty, Megan M.
    Melvin, Sophia J.
    Truax, Nathanyal J.
    Kean, Maeve H.
    Pelkey, Erin T.
    SYNLETT, 2017, 28 (02) : 260 - 264
  • [3] Lewis Acid-Mediated Nucleophilic Addition of Dialkylphosphite to C=N Double Bond of Hydrazones
    Lien, Chia-Ling
    Yeh, Shu-Hua
    Hsu, Chi-Tung
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (03) : 543 - 549
  • [4] Lewis Acid-Catalyzed Nucleophilic Addition of Indoles to in Situ-Generated 2-Amidoallyl Cations
    Schlegel, Marcel
    Schneider, Christoph
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (11): : 5986 - 5992
  • [5] Regioselective C2 Sulfonylation of Indoles Mediated by Molecular Iodine
    Katrun, Praewpan
    Mueangkaew, Charoensak
    Pohmakotr, Manat
    Reutrakul, Vichai
    Jaipetch, Thaworn
    Soorukram, Darunee
    Kuhakarn, Chutima
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (04): : 1778 - 1785
  • [6] SYNTHESIS OF PROCYANIDINS C2 AND C1 USING LEWIS ACID MEDIATED EQUIMOLAR CONDENSATION
    Oizumi, Yukiko
    Katoh, Miyuki
    Hattori, Yasunao
    Toda, Kazuya
    Kawaguchi, Koichiro
    Fujii, Hiroshi
    Makabe, Hidefumi
    HETEROCYCLES, 2012, 85 (09) : 2241 - 2250
  • [7] Nucleophilic addition reaction of aromatic compounds in the presence of Lewis acid
    Lin, JR
    Kanazaki, S
    Kashino, S
    Tsuboi, S
    SYNLETT, 2002, (06) : 899 - 902
  • [8] Lewis Acid Activation of Pyridines for Nucleophilic Aromatic Substitution and Conjugate Addition
    Abou-Shehada, Sarah
    Teasdale, Matthew C.
    Bull, Steven D.
    Wade, Charles E.
    Williams, Jonathan M. J.
    CHEMSUSCHEM, 2015, 8 (06) : 1083 - 1087
  • [9] Nucleophilic addition reaction of aromatic compounds with α-chloroglycidates in the presence of Lewis acid
    Lin, JR
    Gubaidullin, AT
    Mamedov, VA
    Tsuboi, S
    TETRAHEDRON, 2003, 59 (10) : 1781 - 1790
  • [10] Metal-Free Directed C-H Borylation of Indoles at the Sterically Congested C2 Position
    Jiang, Wang
    Bai, Jingyi
    Lv, Jiahang
    Zhao, Yue
    Yan, Chaoguo
    Shi, Zhuangzhi
    SYNLETT, 2023, 34 (18) : 2220 - 2226