Indole-Fused Benzoxepine Synthesis via Visible-Light-Driven Aerobic Dehydrogenative [5+2] Annulation

被引:0
|
作者
Dong, Kui [1 ]
Zhao, Yi-Lin [1 ]
Jin, Xiao-Ling [1 ]
Liu, Qiang [1 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
ALKALOIDS;
D O I
10.1021/acs.orglett.3c03310
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A photocatalyzed oxidative dehydrogenative annulation between 2-(1H-indol-2-yl)-phenols and alkenylphenols is presented. Various indole-fused benzoxepines can be obtained at room temperature using atom-efficient strategies. This method not only avoids the use of stoichiometric amounts of oxidants but also exhibits excellent atom economy by generating H2O as the only theoretical byproduct.
引用
收藏
页码:8258 / 8262
页数:5
相关论文
共 50 条
  • [11] Heterogeneous visible-light promoted dehydrogenative [4+2] annulation of benzothioamides and alkynes under aerobic conditions
    Guo, Yanmin
    Chang, Rong
    Fu, Zhen
    Zhou, Cong-Ying
    Guo, Zhen
    GREEN CHEMISTRY, 2023, 25 (13) : 5206 - 5212
  • [12] Visible-Light-Driven Stereoselective Annulation of Alkyl Anilines and Dibenzoylethylenes via Electron Donor-Acceptor Complexes
    Runemark, August
    Zacharias, Savannah C.
    Sunden, Henrik
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (02): : 1901 - 1910
  • [13] Chemoselective Annulation of 2-Benzothiazolimines Enabled by Bifunctional Phosphonium Salt: Highly Enantioselective Synthesis of Indole-fused Cyclic Thiourea Scaffolds
    Li, Kehan
    Lu, Dongming
    Tan, Jian-Ping
    Ren, Xiaoyu
    Wang, Tianli
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (09)
  • [14] Visible-light-driven three-component annulation for the synthesis of highly functionalized 2-iminothiazolidin-4-ones without photocatalysts
    Yang, Beining
    Wang, Yatang
    Yang, Xiaojuan
    Li, Yinyin
    Zhang, Zhiying
    Hua, Xiaofeng
    Ouyang, Lu
    Zheng, Lvyin
    Guo, Wei
    GREEN CHEMISTRY, 2024, 26 (08) : 4477 - 4483
  • [15] Formal (3+4)-Annulation of Propargylic p-Quinone Methides with 2-Indolylmethanols: Synthesis of Polysubstituted Indole-Fused Oxepines
    Qiu, Zong-Wang
    Li, Bao Qiong
    Liu, Hong-Fu
    Zhu, Zhi-Qiang
    Pan, Han-Peng
    Feng, Na
    Ma, Ai-Jun
    Peng, Jin-Bao
    Zhang, Xiang-Zhi
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (11): : 7490 - 7499
  • [16] Preparation of α-Acyloxy Ketones via Visible-Light-Driven Aerobic Oxo-Acyloxylation of Olefins with Carboxylic Acids
    Zhang, Qing-Bao
    Bang, Yong-Liang
    Zhou, Da-Gang
    Zhou, Pan-Pan
    Wu, Li-Zhu
    Liu, Qiang
    ORGANIC LETTERS, 2016, 18 (20) : 5256 - 5259
  • [17] Synthesis of indole-fused scaffolds via [3+3] cyclization reaction of 2-indolylmethanols with quinone imines
    Qin, Lu-Zhe
    Cheng, Ya-Long
    Wen, Xiaoan
    Xu, Qing-Long
    Zhen, Le
    TETRAHEDRON, 2021, 77
  • [18] Synthesis of (Z)-Cinnamate Derivatives via Visible-Light-Driven E-to-Z Isomerization
    Shu, Penghua
    Xu, Haichang
    Zhang, Lingxiang
    Li, Junping
    Liu, Hao
    Luo, Yuehui
    Yang, Xue
    Ju, Zhiyu
    Xu, Zhihong
    SYNOPEN, 2019, 3 (04): : 103 - 107
  • [19] Visible-Light-Driven Iodine-Catalyzed Synthesis of Unsymmetrical Disulfides via Oxidative Coupling
    Ren, Ming-Zhe
    Fu, Yan-Jun
    Zhang, Bo-Sheng
    Quan, Zheng-Jun
    Wang, Xi-Cun
    SYNTHESIS-STUTTGART, 2023, 55 (13): : 2011 - 2018
  • [20] Visible-light-driven SAQS-catalyzed aerobic oxidative dehydrogenation of alkyl 2-phenylhydrazinecarboxylates
    Van Hieu Tran
    Kim, Hee-Kwon
    RSC ADVANCES, 2022, 12 (47) : 30304 - 30309