Electrochemically Enabled Dehydrogenative Phosphorothiolation of 2H-Indazoles under Electrolyte-Free Conditions

被引:27
作者
Ghosh, Payel [1 ]
Hajra, Alakananda [1 ]
机构
[1] Visva Bharati, Dept Chem, Santini Ketan 731235, W Bengal, India
关键词
Electrooxidation; Phosphorothiolation; cross dehydrogenative coupling; Electrolyte-free; 2H-indazole; BORONIC ACIDS; FUNCTIONALIZATION; AMINATION; ACCESS;
D O I
10.1002/adsc.202200932
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
We have developed an electrochemical method for phosphorothiolation of 2H-indazoles using S-hydrogen phosphorothioates via cross dehydrogenative coupling reaction under metal-free and electrolyte-free conditions. This protocol is compatible with electron donating groups like -Me, -OMe, halogen and elctron withdrawing groups such as -COOEt, affording respective indazolyl phosphorothioates in 62%-91% yields. Comprehensive mechanistic studies indicate that the reaction proceeds through a radical pathway.
引用
收藏
页码:4157 / 4165
页数:9
相关论文
共 67 条
  • [1] Electro-mechanochemical approach towards the chloro sulfoximidations of allenes under solvent-free conditions in a ball mill
    Amer, Mostafa M.
    Hommelsheim, Rene
    Schumacher, Christian
    Kong, Deshen
    Bolm, Carsten
    [J]. FARADAY DISCUSSIONS, 2023, 241 (00) : 79 - 90
  • [2] Visible light promoted cross-dehydrogenative coupling: a decade update
    Bagdi, Avik Kumar
    Rahman, Matiur
    Bhattacherjee, Dhananjay
    Zyryanov, Grigory V.
    Ghosh, Sumit
    Chupakhin, Oleg N.
    Hajra, Alakananda
    [J]. GREEN CHEMISTRY, 2020, 22 (20) : 6632 - 6681
  • [3] Copper-catalyzed reductive coupling of aryl sulfonyl chlorides with H-phosphonates leading to S-aryl phosphorothioates
    Bai, Jie
    Cui, Xiuling
    Wang, Hui
    Wu, Yangjie
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (64) : 8860 - 8863
  • [4] Direct C3 Carbamoylation of 2H-Indazoles
    Bhat, Vighneshwar Shridhar
    Lee, Anna
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (23) : 3382 - 3385
  • [5] Potassium Persulfate Mediated Chemodivergent C-3 Functionalization of 2H-Indazoles with DMSO as C1 Source
    Bhattacharjee, Suvam
    Laru, Sudip
    Ghosh, Payel
    Hajra, Alakananda
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (15) : 10866 - 10873
  • [6] Electrochemical Synthesis of α-Ketoamides under Catalyst-, Oxidant-, and Electrolyte-Free Conditions
    Chen, Jin-Yang
    Wu, Hong-Yu
    Gui, Qing-Wen
    Han, Xiao-Ran
    Wu, Yan
    Du, Kui
    Cao, Zhong
    Lin, Ying-Wu
    He, Wei-Min
    [J]. ORGANIC LETTERS, 2020, 22 (06) : 2206 - 2209
  • [7] Electrochemical Mn-Promoted Radical Selenylation of Boronic Acids with Diselenide Reagents
    Chen, Ziyue
    Wang, Yuan
    Hu, Chenjian
    Wang, Daoxin
    Lei, Peilin
    Yi, Hong
    Yuan, Yong
    Lei, Aiwen
    [J]. ORGANIC LETTERS, 2022, 24 (18) : 3307 - 3312
  • [8] Unparalleled Ease of Access to a Library of Biheteroaryl Fluorophores via Oxidative Cross-Coupling Reactions: Discovery of Photostable NIR Probe for Mitochondria
    Cheng, Yangyang
    Li, Gaocan
    Liu, Yang
    Shi, Yang
    Gao, Ge
    Wu, Di
    Lan, Jingbo
    You, Jingsong
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (14) : 4730 - 4738
  • [9] Paclitaxel, cisplatin and lonidamine in advanced ovarian cancer. A phase II study
    De Lena, M
    Lorusso, V
    Latorre, A
    Fanizza, G
    Gargano, G
    Caporusso, L
    Guida, M
    Catino, A
    Crucitta, E
    Sambiasi, D
    Mazzei, A
    [J]. EUROPEAN JOURNAL OF CANCER, 2001, 37 (03) : 364 - 368
  • [10] Selective N1-Acylation of Indazoles with Acid Anhydrides Using an Electrochemical Approach
    Dissanayake, D. M. M. Mevan
    Vannucci, Aaron K.
    [J]. ORGANIC LETTERS, 2019, 21 (02) : 457 - 460