Copper-mediated construction of benzothieno[3,2-b]benzofurans by intramolecular dehydrogenative C-O coupling reaction

被引：10
作者：
Ai, Liankun [1 ]
Ajibola, Ibrahim Yusuf [1 ]
Li, Baolin [1 ]
机构：
[1] Univ Chinese Acad Sci, Sch Chem Sci, Beijing 100049, Peoples R China
来源：
RSC ADVANCES | 2021年 / 11卷 / 57期
基金：
中国国家自然科学基金;
关键词：
FIELD-EFFECT TRANSISTORS; FLASH VACUUM PYROLYSIS; ORGANIC SEMICONDUCTORS; CYCLIZATION; DIBENZOFURANS; ARYLPHENOLS; DERIVATIVES; TRANSPORT; DESIGN;
D O I：
10.1039/d1ra06985c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient method to synthesize benzothieno[3,2-b]benzofurans via intramolecular dehydrogenative C-H/O-H coupling has been developed. Good to excellent yields (64-91%) could be obtained no matter if the substituted group is electron-donating or electron-withdrawing. Notably, three-to-six fused ring thienofuran compounds could be constructed using this method. A reaction mechanism study showed that 1,1-diphenylethylene can completely inhibit the reaction. Therefore, it is a radical pathway initiated by single electron transfer between the hydroxyl of the substrate and the copper catalyst.
引用
收藏
页码：36305 / 36309
页数：5
相关论文
共 50 条
  • [1] Synthesis of Thieno[3,2-b]benzofurans by Palladium-catalyzed Intramolecular C-H/C-H Coupling
    Kaida, Hiroyuki
    Satoh, Tetsuya
    Hirano, Koji
    Miura, Masahiro
    CHEMISTRY LETTERS, 2015, 44 (08) : 1125 - 1127
  • [2] Synthesis of [1]Benzothieno[3,2-b][1]benzothiophenes through Iodine-Mediated Sulfur Insertion Reaction
    Ito, Kazuki
    Nakamura, Kohei
    Yoshida, Kazuhiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (21)
  • [3] Ullmann-Type Intramolecular C-O Reaction Toward Thieno[3,2-b]furan Derivatives with up to Six Fused Rings
    Chen, Daoliang
    Yuan, Dafei
    Zhang, Cheng
    Wu, Hao
    Zhang, Jianyun
    Li, Baolin
    Zhu, Xiaozhang
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (20) : 10920 - 10927
  • [4] Facile synthesis of [1]benzothieno[3,2-b]benzothiophene from o-dihalostilbenes
    Saito, Masahiko
    Yamamoto, Tatsuya
    Osaka, Itaru
    Miyazaki, Eigo
    Takimiya, Kazuo
    Kuwabara, Hirokazu
    Ikeda, Masaaki
    TETRAHEDRON LETTERS, 2010, 51 (40) : 5277 - 5280
  • [5] Copper-Catalyzed Double Intramolecular Ullmann Coupling for the Synthesis of Diastereomerically and Enantiomerically Pure 4b,9b-Dihydrobenzofuro[3,2-b]benzofurans
    Imrich, Hans-Georg
    Conrad, Juergen
    Beifuss, Uwe
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (35) : 7718 - 7734
  • [6] Efficient synthesis of thieno[3,2-b:4,5-b′]diindoles and benzothieno[3,2-b]-indoles by Pd-catalyzed site-selective C-C and C-N coupling reactions
    Tran Quang Hung
    Tuan Thanh Dang
    Villinger, Alexander
    Tran Van Sung
    Langer, Peter
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (45) : 9041 - 9044
  • [7] Cross dehydrogenative C-O coupling catalysed by a catenane-coordinated copper(i)
    Zhu, Lihui
    Li, Jiasheng
    Yang, Jun
    Au-Yeung, Ho Yu
    CHEMICAL SCIENCE, 2020, 11 (48) : 13008 - 13014
  • [8] Cascade Synthesis of Benzothieno[3,2-b]indoles under Oxidative Conditions Mediated by CuBr and tert-Butyl Hydroperoxide
    Zhao, Xiaoyuan
    Li, Qiao
    Xu, Jun
    Wang, Donghua
    Zhang-Negrerie, Daisy
    Du, Yunfei
    ORGANIC LETTERS, 2018, 20 (18) : 5933 - 5937
  • [9] A Palladium- and Copper-Catalyzed Synthesis of Dihydro[1,2-b]indenoindole-9-ol and Benzofuro[3,2-b]indolines: Metal-Controlled Intramolecular C-C and C-O Bond-Forming Reactions
    Boominathan, Siva Senthil Kumar
    Wang, Jeh-Jeng
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (47) : 17044 - 17050
  • [10] Domino C-N Coupling/Annulation versus C-N Coupling/Hydroamination of 2-Alkynyl-3-bromobenzothiophenes and 2-Alkynyl-3-bromothiophenes. Highly Efficient Synthesis of Benzothieno[3,2-b]quinolines and Thieno[3,2-b]pyrroles
    Salman, Ghazwan Ali
    Hussain, Munawar
    Iaroshenko, Viktor
    Villinger, Alexander
    Langer, Peter
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (2-3) : 331 - 336
12345