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
  • [1] Regioselective C-H chalcogenylation and halogenation of arenes and alkenes under metal-free conditions
    Li, Bin
    Hu, Mingli
    Ge, Jun
    Xu, Wei
    Wu, Jinghan
    Tong, Yao
    Zhao, Zhengyi
    Liu, Xiuxiu
    He, Ling
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (14) : 2910 - 2916
  • [2] Real Metal-Free C-H Arylation of (Hetero)arenes: The Radical Way
    Bellina, Fabio
    SYNTHESIS-STUTTGART, 2021, 53 (15): : 2517 - 2544
  • [3] "Metal-free" electrooxidative C-H thiocyanation of arenes
    Kokorekin, V. A.
    Mel'nikova, E. I.
    Yaubasarova, R. R.
    Gorpinchenko, N. V.
    Petrosyan, V. A.
    RUSSIAN CHEMICAL BULLETIN, 2019, 68 (11) : 2140 - 2141
  • [4] Transition metal-free direct C-H trifluoromethyltion of (hetero)arenes with Togni's reagent
    Chen, Xiaoyu
    Ding, Licheng
    Li, Linlin
    Li, Jingya
    Zou, Dapeng
    Wu, Yangjie
    Wu, Yusheng
    TETRAHEDRON LETTERS, 2020, 61 (09)
  • [5] Metal-Free Oxidative C-H Bond Amination at Ambient Temperature
    Samanta, Rajarshi
    Antonchick, Andrey P.
    SYNLETT, 2012, (06) : 809 - 813
  • [6] Metal-Free, Regioselective, Dehydrogenative Cross-Coupling between Formamides/Aldehydes and Coumarins by C-H Functionalization
    Gupta, Mohit
    Kumar, Prashant
    Bahadur, Vijay
    Kumar, Krishan
    Parmar, Virinder S.
    Singh, Brajendra K.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (07) : 896 - 900
  • [7] Organocatalytic, Oxidative, Intramolecular C-H Bond Amination and Metal-free Cross-Amination of Unactivated Arenes at Ambient Temperature
    Antonchick, Andrey P.
    Samanta, Rajarshi
    Kulikov, Katharina
    Lategahn, Jonas
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) : 8605 - 8608
  • [8] Regioselective C-H Selenylation of Heteroarenes Under Metal-free Conditions
    Schumacher, Ricardo F.
    Cargnelutti, Roberta
    Speranca, Adriane
    Kazmierczak, Jean C.
    Anjos, Thiago
    Hartmann, Cleidi M.
    Godoi, Benhur
    CURRENT ORGANIC CHEMISTRY, 2021, 25 (18) : 2068 - 2088
  • [9] Transition Metal-Free Direct C-H Bond Sulfenylation of Alkenes and Arenes
    Xu, Xinming
    Yang, Hanlin
    Li, Wenzhong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (07) : 1912 - 1925
  • [10] Metal-free radical perfluoroalkylation of (hetero) arenes
    Zhong, Sabilla
    Hafner, Andreas
    Hussal, Christoph
    Nieger, Martin
    Braese, Stefan
    RSC ADVANCES, 2015, 5 (09): : 6255 - 6258
12345