Visible-Light-Induced Organophotoredox-Catalyzed Phosphonylation of 2H-Indazoles with Diphenylphosphine Oxide

被引：92
|
作者：
Singsardar, Mukta [1 ]
Dey, Amrita [1 ]
Sarkar, Rajib [1 ]
Hajra, Alakananda [1 ]
机构：
[1] Visva Bharati, Dept Chem, Santini Ketan 731235, W Bengal, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 20期
关键词：
C-H FUNCTIONALIZATION; PHOTOREDOX CATALYSIS; DIARYLPHOSPHINE OXIDES; EFFICIENT SYNTHESIS; BOND FORMATION; ROSE-BENGAL; IMIDAZOHETEROCYCLES; INHIBITORS; DESIGN; WATER;
D O I：
10.1021/acs.joc.8b02019
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A metal-free visible-light-induced phosphonylation of 2H-indazoles with diphenylphosphine oxide has been developed using rose bengal as an organophotoredox catalyst under ambient air at room temperature. A library of diphenyl(2-phenyl-2H-indazol-3-yl)phosphine oxide with broad functionalities has been synthesized in high yields. The experimental result suggests the radical pathway of the reaction.
引用
收藏
页码：12694 / 12701
页数：8
相关论文
共 50 条
  • [21] Iodine-catalyzed aerobic oxidation of o-alkylazoarenes to 2H-indazoles
    Yi, Xiangli
    Xi, Chanjuan
    TETRAHEDRON, 2017, 73 (10) : 1311 - 1316
  • [22] A General and Mild Palladium-Catalyzed Domino Reaction for the Synthesis of 2H-Indazoles
    Halland, Nis
    Nazare, Marc
    R'kyek, Omar
    Alonso, Jorge
    Urmann, Matthias
    Lindenschmidt, Andreas
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (37) : 6879 - 6882
  • [23] Visible light-promoted transition metal-free direct C3-carbamoylation of 2H-Indazoles
    Ma, Chunhua
    Shang, Linchun
    Zhao, Hanying
    He, Xing
    Lv, Qiyan
    Zhang, Dandan
    Jiang, Yuqin
    FRONTIERS IN CHEMISTRY, 2022, 10
  • [24] Visible-light-induced iron-catalyzed reduction of nitroarenes to anilines
    Yang, Shilei
    He, Min
    Wang, Yi
    Bao, Ming
    Yu, Xiaoqiang
    CHEMICAL COMMUNICATIONS, 2023, 59 (95) : 14177 - 14180
  • [25] Visible-Light-Induced Ni-Catalyzed Radical Borylation of Chloroarenes
    Tian, Ya-Ming
    Guo, Xiao-Ning
    Krummenacher, Ivo
    Wu, Zhu
    Nitsch, Joern
    Braunschweig, Holger
    Radius, Udo
    Marder, Todd B.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (42) : 18231 - 18242
  • [26] Visible-Light-Induced Metal- and Photosensitizer-Free C(sp3)-H Phosphorylation of 3,4-Dihydroquinoxalin-2(1H)-ones with Diphenylphosphine Oxide
    Jia, Li
    Lu, Yanan
    Chen, Ying
    Zhong, Yu
    Zhao, Fen
    Zhou, Yongyun
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (16): : 11659 - 11664
  • [27] Visible-Light-Induced Copper-Catalyzed Alkynylation/Alkylation of Alkenes
    Zhang, Yajing
    Zhang, Dayong
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05): : 3213 - 3223
  • [28] Visible-Light Photocatalyzed C3-H Alkylation of 2H-Indazoles/Indoles with Sulfoxonium Ylides via Diversified Mechanistic Pathways
    Peng, Yuzhu
    Wang, Yujing
    Wang, Kaifeng
    Sun, Qing
    Bao, Xiaoguang
    ACS CATALYSIS, 2024, 14 (02) : 1193 - 1204
  • [29] Silver-catalyzed radical reaction of 2H-indazoles with 1,3-dicarbonyl compounds to access 3-dicarbonyl indazoles
    Li, Zhen-Hua
    Wang, Wen-Biao
    Qin, Jin-Jing
    Ye, Li-Xian
    He, Jia-Yu
    Xie, Yuan-Yuan
    TETRAHEDRON, 2021, 91
  • [30] Visible-light-induced palladium-catalyzed C-H acylation of Azobenzenes at room temperature
    Xie, Pan
    Zhao, Xuyang
    Xue, Cheng
    Wen, Feifei
    Du, Dongdong
    Zhang, Wanying
    MOLECULAR CATALYSIS, 2024, 569
12345