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
  • [1] Organophotoredox-Catalyzed Direct C-H Amination of 2H-Indazoles with Amines
    Neogi, Sukanya
    Ghosh, Asim Kumar
    Majhi, Koushik
    Samanta, Sadhanendu
    Kibriya, Golam
    Hajra, Alakananda
    ORGANIC LETTERS, 2020, 22 (14) : 5605 - 5609
  • [2] Visible-Light-Induced Regioselective Cross-Dehydrogenative Coupling of 2H-Indazoles with Ethers
    Singsardar, Mukta
    Lam, Sudip
    Mondal, Susmita
    Hajra, Alakananda
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (07): : 4543 - 4550
  • [3] Visible Light-Induced Organophotoredox-Catalyzed β-Hydroxytrifluoromethylation of Unactivated Alkenes
    Behera, Mousumi
    Dharpure, Pankaj D.
    Sahu, Ajit K.
    Bhat, Ramakrishna G.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (20): : 14695 - 14709
  • [4] Visible light-induced organophotoredox-catalyzed difunctionalization of alkenes and alkynes
    Gupta, Subham
    Kundu, Abhishek
    Ghosh, Sumit
    Chakraborty, Amrita
    Hajra, Alakananda
    GREEN CHEMISTRY, 2023, 25 (21) : 8459 - 8493
  • [5] Visible-light-induced Mn(0)-catalyzed direct C-3 mono-, di- and perfluoroalkylation reactions of 2H-indazoles
    Laru, Sudip
    Bhattacharjee, Suvam
    Hajra, Alakananda
    CHEMICAL COMMUNICATIONS, 2022, 58 (98) : 13604 - 13607
  • [6] Visible-Light Organophotoredox-Catalyzed Synthesis of Precursors for Horner-Type Olefinations
    Nebe, Marco M.
    Loeper, Daniel
    Fuermeyer, Fabian
    Opatz, Till
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (20-21) : 2471 - 2476
  • [7] Visible-Light-Induced Remote C(sp3)-H Phosphonylation of Amides
    Xiang Panjie
    Yu Bing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (06) : 2057 - 2058
  • [8] Visible-Light-Induced Regioselective ortho-C-H Phosphonylation of β-Naphthols with Diarylphosphine Oxides
    Yuan Jinwei
    Liu Yan
    Ge Yuanyuan
    Dong Shaoxuan
    Song Saiyi
    Yang Liangru
    Xiao Yongmei
    Zhang Shouren
    Qu Lingbo
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (12) : 4738 - 4748
  • [9] Visible-Light-Promoted Direct C3-H Cyanomethylation of 2H-Indazoles
    Mi, Xia
    Cui, Beibei
    Song, Jinqing
    Zhang, Jingyu
    ACS OMEGA, 2023, 8 (12): : 11192 - 11200
  • [10] Organophotoredox-Catalyzed C(sp2)-H Difluoromethylenephosphonation of Imidazoheterocycles
    Singsardar, Mukta
    Mondal, Susmita
    Laru, Sudip
    Hajra, Alakananda
    ORGANIC LETTERS, 2019, 21 (14) : 5606 - 5610
12345