Hydroarylative cyclization of enynes with aromatic ketones catalyzed by a low-valent iron-phosphine complex

被引：0
作者：
Kitazawa, Yoichi [1 ]
Kochi, Takuya [1 ]
Kakiuchi, Fumitoshi [1 ,2 ]
机构：
[1] Keio Univ, Fac Sci & Technol, Dept Chem, 3-14-1 Hiyoshi,Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
[2] JST, CREST, JPMJCR20R1, 4-1-8 Honcho, Kawaguchi, Saitama 3320012, Japan
来源：
TETRAHEDRON LETTERS | 2025年 / 155卷
关键词：
Iron catalyst; C -H bond cleavage; Aromatic ketones; Enynes; Cycloaddition; 1,6-ENYNES; ACTIVATION;
D O I：
10.1016/j.tetlet.2024.155409
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report here an iron-catalyzed C-H functionalization of aromatic ketones via cyclization of enynes. The reaction is applicable to a variety of aromatic ketones and enables regioselective introduction of a hydrogen atom and an aryl group at the alkyne moiety and the olefin moiety, respectively.
引用
收藏
页数：5
相关论文
共 24 条
  • [1] Iron-Catalyzed C-H Functionalization Processes
    Cera, Gianpiero
    Ackermann, Lutz
    [J]. TOPICS IN CURRENT CHEMISTRY, 2016, 374 (05)
  • [2] Ligand Effects in Carboxylic Ester- and Aldehyde-Assisted β-C-H Activation in Regiodivergent and Enantioselective Cycloisomerization-Hydroalkenylation and Cycloisomerization-Hydroarylation, and [2+2+2]-Cycloadditions of 1,6-Enynes
    Ghosh, Kiron K.
    RajanBabu, T. V.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, : 18753 - 18770
  • [3] Cationic Co(I) Catalysts for Regiodivergent Hydroalkenylation of 1,6-Enynes: An Uncommon cis-β-C-H Activation Leads to Z-Selective Coupling of Acrylates
    Herbort, James H.
    Lalisse, Remy F.
    Hadad, Christopher M.
    RajanBabu, T., V
    [J]. ACS CATALYSIS, 2021, 11 (15) : 9605 - 9617
  • [4] Metal-catalyzed enyne cycloisomerization in natural product total synthesis
    Hu, Ying
    Bai, Miao
    Yang, Ying
    Zhou, Qianghui
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (11): : 2256 - 2275
  • [5] Chiral Diene Ligands in Asymmetric Catalysis
    Huang, Yinhua
    Hayashi, Tamio
    [J]. CHEMICAL REVIEWS, 2022, 122 (18) : 14346 - 14404
  • [6] Iron/Photosensitizer-Catalyzed Directed C-H Activation Triggered by the Formation of an Iron Metallacycle
    Kato, Yoshimi
    Yoshino, Tatsuhiko
    Matsunaga, Shigeki
    [J]. ACS CATALYSIS, 2023, 13 (07) : 4552 - 4559
  • [7] KHAND IU, 1971, J CHEM SOC CHEM COMM, P36
  • [8] Deuterium-Labeling Studies on the C-H/Olefin Coupling of Aromatic Ketones Catalyzed by Fe(PMe3)4
    Kimura, Naoki
    Katta, Shiori
    Kitazawa, Yoichi
    Kochi, Takuya
    Kakiuchi, Fumitoshi
    [J]. SYNTHESIS-STUTTGART, 2021, 53 (18): : 3383 - 3389
  • [9] Iron-Catalyzed Ortho C-H Homoallylation of Aromatic Ketones with Methylenecyclopropanes
    Kimura, Naoki
    Katta, Shiori
    Kitazawa, Yoichi
    Kochi, Takuya
    Kakiuchi, Fumitoshi
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (12) : 4543 - 4549
  • [10] Iron-Catalyzed Regioselective Anti-Markovnikov Addition of C-H Bonds in Aromatic Ketones to Alkenes
    Kimura, Naoki
    Kochi, Takuya
    Kakiuchi, Fumitoshi
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (42) : 14849 - 14852
123