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

被引:29
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 [J].
Amer, Mostafa M. ;
Hommelsheim, Rene ;
Schumacher, Christian ;
Kong, Deshen ;
Bolm, Carsten .
FARADAY DISCUSSIONS, 2023, 241 (00) :79-90
[2]   Visible light promoted cross-dehydrogenative coupling: a decade update [J].
Bagdi, Avik Kumar ;
Rahman, Matiur ;
Bhattacherjee, Dhananjay ;
Zyryanov, Grigory V. ;
Ghosh, Sumit ;
Chupakhin, Oleg N. ;
Hajra, Alakananda .
GREEN CHEMISTRY, 2020, 22 (20) :6632-6681
[3]   Copper-catalyzed reductive coupling of aryl sulfonyl chlorides with H-phosphonates leading to S-aryl phosphorothioates [J].
Bai, Jie ;
Cui, Xiuling ;
Wang, Hui ;
Wu, Yangjie .
CHEMICAL COMMUNICATIONS, 2014, 50 (64) :8860-8863
[4]   Direct C3 Carbamoylation of 2H-Indazoles [J].
Bhat, Vighneshwar Shridhar ;
Lee, Anna .
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 [J].
Bhattacharjee, Suvam ;
Laru, Sudip ;
Ghosh, Payel ;
Hajra, Alakananda .
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (15) :10866-10873
[6]   Electrochemical Synthesis of α-Ketoamides under Catalyst-, Oxidant-, and Electrolyte-Free Conditions [J].
Chen, Jin-Yang ;
Wu, Hong-Yu ;
Gui, Qing-Wen ;
Han, Xiao-Ran ;
Wu, Yan ;
Du, Kui ;
Cao, Zhong ;
Lin, Ying-Wu ;
He, Wei-Min .
ORGANIC LETTERS, 2020, 22 (06) :2206-2209
[7]   Electrochemical Mn-Promoted Radical Selenylation of Boronic Acids with Diselenide Reagents [J].
Chen, Ziyue ;
Wang, Yuan ;
Hu, Chenjian ;
Wang, Daoxin ;
Lei, Peilin ;
Yi, Hong ;
Yuan, Yong ;
Lei, Aiwen .
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 [J].
Cheng, Yangyang ;
Li, Gaocan ;
Liu, Yang ;
Shi, Yang ;
Gao, Ge ;
Wu, Di ;
Lan, Jingbo ;
You, Jingsong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (14) :4730-4738
[9]   Paclitaxel, cisplatin and lonidamine in advanced ovarian cancer. A phase II study [J].
De Lena, M ;
Lorusso, V ;
Latorre, A ;
Fanizza, G ;
Gargano, G ;
Caporusso, L ;
Guida, M ;
Catino, A ;
Crucitta, E ;
Sambiasi, D ;
Mazzei, A .
EUROPEAN JOURNAL OF CANCER, 2001, 37 (03) :364-368
[10]   Selective N1-Acylation of Indazoles with Acid Anhydrides Using an Electrochemical Approach [J].
Dissanayake, D. M. M. Mevan ;
Vannucci, Aaron K. .
ORGANIC LETTERS, 2019, 21 (02) :457-460