Metal-free regioselective C-H chalcogenylation of coumarins/(hetero)arenes at ambient temperature

被引：57
|
作者：
Song, Zengqiang [1 ]
Ding, Chaochao [1 ]
Wang, Shaoli [1 ]
Dai, Qian [1 ]
Sheng, Yaoguang [1 ]
Zheng, Zhilong [1 ]
Liang, Guang [1 ]
机构：
[1] Wenzhou Med Univ, Sch Pharmaceut Sci, Chem Biol Res Ctr, Wenzhou 325035, Zhejiang, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2020年 / 56卷 / 12期
基金：
中国国家自然科学基金;
关键词：
S BOND; COUMARINS; DERIVATIVES; FUNCTIONALIZATION; HETEROARYLATION; DICHALCOGENIDES; CHALCOGENATION; (HETERO)ARENES; DISELENIDES; OLEFINATION;
D O I：
10.1039/c9cc09001k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel, practical and metal-free approach for the regioselective selenation of coumarins employing (bis(trifluoroacetoxy)iodo)benzene (PIFA) at room temperature is presented. The developed method is suitable for a wide substrate scope and affords 3-selenyl coumarins in good to excellent yields with high selectivity. A radical mechanism is proposed for this new transformation. Furthermore, the application of sulfenylation with coumarines and selenation with other (hetero)arenes in this transformation is successful.
引用
收藏
页码：1847 / 1850
页数：4
相关论文
共 50 条
  • [21] Metal-free photoredox-catalysed formal C-H/C-H coupling of arenes enabled by interrupted Pummerer activation
    Aukland, Miles H.
    Siauciulis, Mindaugas
    West, Adam
    Perry, Gregory J. P.
    Procter, David J.
    NATURE CATALYSIS, 2020, 3 (02) : 163 - 169
  • [22] Selective C-H Iodination of (Hetero)arenes
    Tanwar, Lalita
    Boergel, Jonas
    Lehmann, Johannes
    Ritter, Tobias
    ORGANIC LETTERS, 2021, 23 (13) : 5024 - 5027
  • [23] Photocatalytic C-H Trifluoroethoxylation of (Hetero)arenes
    Chen, Mingxi
    Ling, Jingjing
    Cheng, Keguang
    Wang, Quande
    ORGANIC LETTERS, 2025, 27 (09) : 2241 - 2246
  • [24] Synthesis of Aryl Sulfides: Metal-Free C-H Sulfenylation of Electron-Rich Arenes
    Hostier, Thomas
    Ferey, Vincent
    Ricci, Gino
    Pardo, Domingo Gomez
    Cossy, Janine
    ORGANIC LETTERS, 2015, 17 (15) : 3898 - 3901
  • [25] Metal-Free Allylic C-H Amination
    Murakami, Suguru
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2023, 81 (03) : 267 - 268
  • [26] Metal-free directed C-H borylation
    Xu, Ming-Hua
    CHINESE SCIENCE BULLETIN-CHINESE, 2020, 65 (05): : 331 - 333
  • [27] Metal-free photoanodes for C-H functionalization
    Zhang, Junfang
    Zhu, Yuntao
    Njel, Christian
    Liu, Yuxin
    Dallabernardina, Pietro
    Stevens, Molly M.
    Seeberger, Peter H.
    Savateev, Oleksandr
    Loeffler, Felix F.
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [28] Metal-Free Allylic C-H Amination
    Murakami S.
    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 2023, 81 (03): : 267 - 268
  • [29] 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
  • [30] 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
12345