Regioselective C-H Phosphorothiolation of (Hetero)arenes Enabled by the Synergy of Electrooxidation and Ultrasonic Irradiation

被引：49
|
作者：
Meng, Ze-Yin [1 ,2 ]
Feng, Cheng-Tao [1 ,2 ]
Zhang, Ling [2 ]
Yang, Qing [2 ]
Chen, De-Xiang [2 ]
Xu, Kun [3 ]
机构：
[1] Anhui Univ Chinese Med, Sch Pharm, Hefei 230012, Peoples R China
[2] Anhui Univ Sci & Technol, Sch Chem Engn, Huainan 232001, Peoples R China
[3] Beijing Univ Technol, Fac Environm & Life, Beijing 100124, Peoples R China
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 11期
关键词：
ARYL; ACIDS;
D O I：
10.1021/acs.orglett.1c01161
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An electrochemically regioselective C-H phosphorothiolation of (hetero)arenes with thiocyanate as the S source under ultrasonic irradiation has been developed. The synergistic cooperation of electrooxidation and ultrasonication markedly accelerated the C-H phosphorothiolation reaction. This mechanistically different method is distinguished by its wide substrate scope and transition-metal-free and external-oxidant-free conditions, thus complementing the existing metal-catalyzed or peroxide-mediated protocols for the green synthesis of S-(hetero)aryl phosphorothioates.
引用
收藏
页码：4214 / 4218
页数：5
相关论文
共 50 条
  • [1] Selective C-H Iodination of (Hetero)arenes
    Tanwar, Lalita
    Boergel, Jonas
    Lehmann, Johannes
    Ritter, Tobias
    ORGANIC LETTERS, 2021, 23 (13) : 5024 - 5027
  • [2] Photocatalytic C-H Trifluoroethoxylation of (Hetero)arenes
    Chen, Mingxi
    Ling, Jingjing
    Cheng, Keguang
    Wang, Quande
    ORGANIC LETTERS, 2025, 27 (09) : 2241 - 2246
  • [3] NIS/TBHP Induced Regioselective Selenation of (Hetero)Arenes via Direct C-H Functionalization
    Ding, Chaochao
    Yu, Yuanzu
    Yu, Qiongli
    Xie, Zixin
    Zhou, Yan
    Zhou, Jianmin
    Liang, Guang
    Song, Zengqiang
    CHEMCATCHEM, 2018, 10 (23) : 5397 - 5401
  • [4] Ru-Catalyzed Regioselective Direct Hydroxymethylation of (Hetero)Arenes via C-H Activation
    Zhang, Guo-Fu
    Li, Yue
    Xie, Xiao-Qiang
    Ding, Cheng-Rong
    ORGANIC LETTERS, 2017, 19 (05) : 1216 - 1219
  • [5] Metal-free regioselective C-H chalcogenylation of coumarins/(hetero)arenes at ambient temperature
    Song, Zengqiang
    Ding, Chaochao
    Wang, Shaoli
    Dai, Qian
    Sheng, Yaoguang
    Zheng, Zhilong
    Liang, Guang
    CHEMICAL COMMUNICATIONS, 2020, 56 (12) : 1847 - 1850
  • [6] Recent Progress in Iridium-Catalyzed Remote Regioselective C-H Borylation of (Hetero)Arenes
    Zou, Xiaoliang
    Xu, Senmiao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (07) : 2610 - 2620
  • [7] Direct Perfluoroalkylation of C-H Bonds in (Hetero)arenes
    Baguia, Hajar
    Evano, Gwilherm
    CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (41)
  • [8] Direct C-H trifluoromethylthiolation of (hetero)arenes: A review
    Hamzehloo, Majid
    Hosseinian, Akram
    Ebrahimiasl, Saeideh
    Monfared, Aazam
    Vessally, Esmail
    JOURNAL OF FLUORINE CHEMISTRY, 2019, 224 : 52 - 60
  • [9] Photocatalytic regioselective C-H bond functionalizations in arenes
    Hu, Jun
    Pradhan, Suman
    Waiba, Satyadeep
    Das, Shoubhik
    CHEMICAL SCIENCE, 2025, 16 (03) : 1041 - 1070
  • [10] Oxidative C-H/C-H Coupling Reactions between Two (Hetero)arenes
    Yang, Yudong
    Lan, Jingbo
    You, Jingsong
    CHEMICAL REVIEWS, 2017, 117 (13) : 8787 - 8863
12345