Silica gel-Mediated Friedel-Crafts Reaction of lndoles with Functionalized Nitroallylic Acetates via an SN1 Process

被引:2
|
作者
Ho, Ching-Yin [1 ]
Roy, Suparna [1 ]
Chen, Yan-Ming [1 ]
Chen, Kwunmin [1 ]
机构
[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan
关键词
Friedel-Crafts reaction; Indole; Nitroallylic acetate; Electrophile; S(N)1; CATALYZED ALLYLIC ALKYLATION; NONREARRANGED MONOTERPENOID UNIT; SIMPLE INDOLE ALKALOIDS; IONIC LIQUIDS; ARYL HALIDES; ALCOHOLS; BENZENE; LIGANDS; KETONES;
D O I
10.1002/jccs.201100643
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An environmentally friendly Friedel-Crafts reaction was demonstrated between indoles and functionalized nitroallylic acetates in the presence of silica gel, providing the corresponding C-3-selective regioisomers in good to high overall chemical yields (70-93%).
引用
收藏
页码:940 / 946
页数:7
相关论文
共 32 条
  • [1] Organocatalytic Friedel-Crafts Benzylation of Heteroaromatic and Aromatic Compounds via an SN1 Pathway
    Watanabe, Naruhisa
    Matsugi, Aoi
    Nakano, Keiji
    Ichikawa, Yoshiyasu
    Kotsuki, Hiyoshizo
    SYNLETT, 2014, 25 (03) : 438 - 442
  • [2] Route to Functionalized Tetrahydrobenzo[d]azepines via Re2O7-Mediated Intramolecular Friedel-Crafts Reaction
    Zheng, Yuzhu
    Huang, Qing
    Fang, Xiong
    Xie, Youwei
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (03): : 2001 - 2008
  • [3] Silica gel-mediated rearrangement of allylic acetates. Application to the synthesis of 1,3-enynes
    Serra-Muns, Anna
    Guerinot, Amandine
    Reymond, Sebastien
    Cossy, Janine
    CHEMICAL COMMUNICATIONS, 2010, 46 (23) : 4178 - 4180
  • [4] Synthesis of Spiroindanyl-2-oxindoles via PPA-mediated Intramolecular Friedel-Crafts Reaction
    Seo, Da Young
    Min, Beom Kyu
    Roh, Hwa Jung
    Kim, Jae Nyoung
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2017, 38 (10): : 1231 - 1234
  • [5] Silane-Mediated Alkylation of Arenes via Reductive Friedel-Crafts Reaction Using Carbonyl Compounds
    Khan, Jabir
    Mahato, Rina
    Kanhaiya, Chinmoy
    Hazra, Chinmoy Kumar
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (11)
  • [6] Synthesis of functionalized 3-chloro-1-naphthols via Friedel-Crafts acylation of vinyl chlorides
    Xin Linghu
    McLaughlin, Mark
    Chen, Cheng-yi
    Reamer, Robert A.
    Dimichele, Lisa
    Davies, Ian W.
    TETRAHEDRON LETTERS, 2012, 53 (13) : 1550 - 1552
  • [7] Synthesis of dihydroindeno[1,2-c] isochromene via cascade cyclization and Friedel-Crafts reaction
    Saikia, Anil K.
    Ghosh, Priya
    Deka, Manash Jyoti
    Borah, Madhurjya
    RSC ADVANCES, 2016, 6 (108): : 106656 - 106661
  • [8] Rapid and Scalable Preparation of High-Crystalline Carboxyl-Functionalized Covalent Triazine Frameworks via Friedel-Crafts Reaction
    Zhang, Lei
    Sun, Tian
    Zhang, Zhao
    Zhang, Ziyue
    Xu, Yuxi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (10)
  • [9] Silica Gel Mediated Friedel-Crafts Alkylation of 3-Indolylmethanols with Indoles: Synthesis of Unsymmetrical Bis(3-indolyl)methanes
    Zou, Yongzhen
    Chen, Cuili
    Chen, Xianxiao
    Zhang, Xiaoxiang
    Rao, Weidong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (16) : 2266 - 2271
  • [10] An Efficient and Green Synthesis of 1-Indanone and 1-Tetralone via Intramolecular Friedel-Crafts Acylation Reaction
    Phuong Hoang Tran
    Vy Hieu Huynh
    Hansen, Poul Erik
    Duy-Khiem Nguyen Chau
    Thach Ngoc Le
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (05) : 482 - 486