C-H functionalization of (hetero)arenes: Direct selanylation mediated by Selectfluor

被引:22
|
作者
Belladona, Andrei L. [1 ]
Cervo, Rodrigo [1 ]
Alves, Diego [2 ]
Barcellos, Thiago [3 ]
Cargnelutti, Roberta [1 ]
Schumacher, Ricardo F. [1 ]
机构
[1] Fed Univ Santa Maria UFSM, Dept Chem, BR-97105900 Santa Maria, RS, Brazil
[2] Fed Univ Pelotas UFPel, CCQFA, LASOL, POB 354, BR-96010310 Pelotas, RS, Brazil
[3] Univ Caxias UCS, Lab Biotechnol Nat & Synthet Prod, Caxias Do Sul, RS, Brazil
关键词
Selectfluor; N-Heterocycles; Diaryl diselenide; Selanylation reaction; C-H functionalization; ASSISTED SYNTHESIS; DERIVATIVES; ANTIOXIDANT; EFFICIENT; INDOLES; THIOLATION; SELENATION; SELENIDES; ARENES; CUI;
D O I
10.1016/j.tetlet.2020.152035
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The direct selanylation of a diverse array of (hetero)arenes, including imidazo[2, 1-b]thiazole, imidazo [1, 2-a]pyridine, 1H-indole, 1H-pyrazole, isoxazole and naphthalen-2-ol is presented. The reactions are mediated by Selectfluor, as a stable, easy to handle and commercially available oxidant. The methodology features simple, mild and safe reaction conditions to produce non-symmetrical diorganyl selenides in moderate to excellent yields. The reactions were conducted at room temperature in air using NaHCO3 in acetonitrile. (C) 2020 Elsevier Ltd. All rights reserved.
引用
收藏
页数:4
相关论文
共 50 条
  • [1] 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
  • [2] Direct Perfluoroalkylation of C-H Bonds in (Hetero)arenes
    Baguia, Hajar
    Evano, Gwilherm
    CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (41)
  • [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] Electrochemical C-H Functionalization of (Hetero)Arenes-Optimized by DoE
    Doerr, Maurice
    Roeckl, Johannes L.
    Rein, Jonas
    Schollmeyer, Dieter
    Waldvogel, Siegfried R.
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (45) : 10195 - 10198
  • [5] C-H Bond Functionalization of N-Heteroarenes Mediated by Selectfluor
    Romero, Angel H.
    TOPICS IN CURRENT CHEMISTRY, 2023, 381 (05)
  • [6] Visible light mediated C-H trifluoromethylation of (hetero)arenes
    Xiao, Fang
    Jin-Hong Lin
    Hao, Fei
    Zheng, Xing
    Guo, Yu
    Ji-Chang Xiao
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (07) : 1982 - 1985
  • [7] Rhodium-Catalyzed Direct C-H Phosphorylation of (Hetero)arenes Suitable for Late-Stage Functionalization
    Min, Minsik
    Kang, Dahye
    Jung, Sungwoo
    Hong, Sungwoo
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (08) : 1296 - 1301
  • [8] Sustainable protocols for direct C-H bond arylation of (hetero)arenes
    Albano, Gianluigi
    Punzi, Angela
    Capozzi, Maria Annunziata M.
    Farinola, Gianluca M.
    GREEN CHEMISTRY, 2022, 24 (05) : 1809 - 1894
  • [9] t-BuONa-mediated direct C-H halogenation of electron-deficient (hetero) arenes
    Liu, Xia
    Zhao, Xin
    Liang, Fushun
    Ren, Baoyi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (06) : 886 - 890
  • [10] C-H hetero-functionalization of arenes through palladacyclopentane-type intermediates
    Cao, Liming
    Hua, Yu
    Cheng, Hong-Gang
    Zhou, Qianghui
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (14): : 3883 - 3914