Visible-light-induced C(sp3)-H bromination of 4-methylthiophene derivatives with HBr/H2O2

被引：2
|
作者：
Song, Wenbo [1 ,2 ]
Ma, Ming [1 ,2 ]
Zhang, Wenjing [1 ,2 ]
Feng, Ranran [1 ,2 ]
Lu, Congcong [1 ,2 ]
Zhang, Hong-Yu [1 ,2 ]
Zhang, Yuecheng [1 ,3 ]
Zhao, Jiquan [1 ,2 ]
机构：
[1] Hebei Univ Technol, Sch Chem Engn & Technol, Tianjin 300131, Peoples R China
[2] Hebei Prov Key Lab Green Chem Technol & High Effic, Tianjin 300131, Peoples R China
[3] Hebei Univ Technol, Natl Local Joint Engn Lab Energy Conservat Chem Pr, Tianjin 300130, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2024年 / 22卷 / 20期
关键词：
SOLVENT-FREE BROMINATION; TAK-385; RELUGOLIX; GNRH ANTAGONIST; H2O2-HBR; KETONES; SYSTEM;
D O I：
10.1039/d4ob00547c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient method to synthesize ethyl 4-(bromomethyl)thiophene-3-carboxylate derivatives has been developed via a visible-light-induced radical process in good yields and with wide functional group tolerance under air conditions and at ambient temperature. The present protocol has the advantages of a high atom economy, easy purification, and environmental friendliness as it employs HBr as the bromine source and the cheap and low-toxic H2O2 as the oxidant. The synthetic utility of this method is demonstrated by a gram scale reaction and its application in the innovative synthesis of the clinical drug relugolix.
引用
收藏
页码：4145 / 4152
页数：8
相关论文
共 50 条
  • [21] Visible-Light-Promoted Radical Cross-Dehydrogenative Coupling of C(sp3)-H/C(sp3)-H and C(sp3)-H/C(sp2)-H via Intermolecular HAT
    Xie, Xinpeng
    Qiao, Kaikai
    Shao, Bing-ru
    Jiang, Wenfeng
    Shi, Lei
    ORGANIC LETTERS, 2023, 25 (23) : 4264 - 4269
  • [22] Visible-light-induced methylsulfonylation/bicyclization of C(sp3)-tethered 1,7-enynes using a DMSO/H2O system
    Huang, Min-Hua
    Zhu, Chi-Fan
    He, Chun-Lan
    Zhu, Yi-Long
    Hao, Wen-Juan
    Wang, De-Cai
    Tu, Shu-Jiang
    Jiang, Bo
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (10): : 1643 - 1650
  • [23] Visible-light induced C(sp3)-H arylation of glycine derivatives by cerium catalysis
    Wang, Shutao
    Ye, Yanjie
    Shen, Hailong
    Liu, Jiyu
    Liu, Zhao
    Jiang, Zhigen
    Lei, Junqiang
    Zhang, Yuan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (41) : 8364 - 8371
  • [24] Visible-light-induced intramolecular sp3 C-H oxidation of 2-alkyl-substituted benzamides for the synthesis of functionalized iminoisobenzofurans
    Wu, Lingang
    Hao, Yanan
    Liu, Yuxiu
    Wang, Qingmin
    CHEMICAL COMMUNICATIONS, 2019, 55 (92) : 13908 - 13911
  • [25] Visible-light-induced C(sp3)-H functionalizations of piperidines to 3,3-dichloro-2-hydroxy-piperidines with N-chlorosuccinimide
    Wang, Fang
    Liu, Xiaoli
    Wang, Lei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (27) : 6141 - 6146
  • [26] Visible-Light-Induced N-Radical Directed Remote Functionalization of sp3 C-H Bonds
    Xiao Li
    Li Jiaheng
    Wang Ting
    ACTA CHIMICA SINICA, 2019, 77 (09) : 841 - 849
  • [27] Visible-Light-Induced Difluoroalkylation of C(sp3)-H Bonds with Trimethylsilyl Chloride as a Dual-Function Reagent
    Wang, Xiaochen
    Wu, Senhui
    Ding, Pengxuan
    Liu, Yuxiu
    Song, Hongjian
    Wang, Qingmin
    ADVANCED SYNTHESIS & CATALYSIS, 2025,
  • [28] Visible-Light-Induced Direct Thiolation at α-C(sp3)-H of Ethers with Disulfides Using Acridine Red as Photocatalyst
    Zhu, Xianjin
    Xie, Xiaoyu
    Li, Pinhua
    Guo, Jianqi
    Wang, Lei
    ORGANIC LETTERS, 2016, 18 (07) : 1546 - 1549
  • [29] Visible-Light-Induced Mpg-C3N4 Catalyzed C(sp2)-H Thiocyanation of Ketene Dithioacetals
    Yin, Fumeng
    Hu, Shan
    Zhu, Shuwei
    Xing, Shifeng
    Zhu, Hongjun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 28 (04)
  • [30] Photocatalytic Visible-Light-Induced Nitrogen Insertion via Dual C(sp3)-H and C(sp2)-H Bond Functionalization: Access to Privileged Imidazole-based Scaffolds
    Patel, Srilaxmi M.
    Prasad, Ermiya P.
    Bakthadoss, Manickam
    Sharada, Duddu S.
    ORGANIC LETTERS, 2021, 23 (02) : 257 - 261
12345