Visible-Light-Promoted Trifluoromethylthiolation and Trifluoromethylselenolation of 1,4-Dihydropyridines

被引：13
|
作者：
Shan, Xiwen [1 ]
Wang, Xiaoxing [1 ]
Chen, Enxue [1 ]
Liu, Juyan [1 ]
Lu, Kui [1 ]
Zhao, Xia [1 ]
机构：
[1] Tianjin Normal Univ, Coll Chem, Tianjin Key Lab Struct & Performance Funct Mol, Tianjin 300387, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 01期
基金：
中国国家自然科学基金;
关键词：
ELECTRON-RICH AROMATICS; TRIFLUOROMETHANESULFONYL CHLORIDE; ALKENES; INDOLES; ESTERS; DIFLUOROMETHYLTHIOLATION; REAGENTS; CF3SO2NA;
D O I：
10.1021/acs.joc.2c02348
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report a metal-free trifluoromethylthiolation and trifluoromethylselenolation of 1,4-dihydropyridines with S-(tri-fluoromethyl) 4-methylbenzenesulfonothioate and Se-(trifluoro-methyl) 4-methylbenzenesulfonoselenoate under visible light irradiation. This transformation was tolerated with a wide range of functional groups and provided an alternative and green strategy for the synthesis of trifluoromethylthioesters and trifluoromethyl-selenoesters.
引用
收藏
页码：319 / 328
页数：10
相关论文
共 50 条
  • [21] Visible-light-promoted sulfonylmethylation of imidazopyridines
    Xia Mi
    Yuanfang Kong
    Jingyu Zhang
    Chao Pi
    Xiuling Cui
    Chinese Chemical Letters, 2019, 30 (12) : 2295 - 2298
  • [22] Visible-Light-Promoted Synthesis of Benzimidazoles
    Park, Sehyun
    Jung, Jaehun
    Cho, Eun Jin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (19) : 4148 - 4154
  • [23] NEW SYNTHESIS OF 1,4-DIHYDROPYRIDINES
    CHENNAT, T
    EISNER, U
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (10): : 926 - 929
  • [24] Vicinal diamination of 1,4-dihydropyridines
    Lavilla, R
    Kumar, R
    Coll, O
    Masdeu, C
    Bosch, J
    CHEMICAL COMMUNICATIONS, 1998, (24) : 2715 - 2716
  • [25] Progress in Synthesis of 1,4-Dihydropyridines
    Lu, Lingling
    Xu, Hui
    Zhou, Pan
    Yu, Fuchao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (12) : 2858 - 2879
  • [26] NOVEL FLUORESCENT 1,4-DIHYDROPYRIDINES
    NAIR, V
    OFFERMAN, RJ
    TURNER, GA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1986, 192 : 271 - ORGN
  • [27] Novel Oxidation of 1,4-Dihydropyridines
    Hatamjafari, Farhad
    Montazeri, Nasser
    Pourshamsian, Khalil
    ASIAN JOURNAL OF CHEMISTRY, 2011, 23 (07) : 3287 - 3288
  • [28] Metal-Free-Mediated Oxidation Aromatization of 1,4-Dihydropyridines to Pyridines Using Visible Light and Air
    Wei, Xiaojing
    Wang, Lin
    Jia, Wenliang
    Du, Shaofu
    Wu, Lizhu
    Liu, Qiang
    CHINESE JOURNAL OF CHEMISTRY, 2014, 32 (12) : 1245 - 1250
  • [29] Copper-Catalyzed Cyanoalkylation and Trifluoromethylthiolation of Styrene Derivatives via a Visible-Light-Promoted Cross-Coupling
    Xu, Xiao-Jing
    Chi, Zhuo-Min
    Rui, Rong
    Zhang, Zhe
    Li, Hong-Zhe
    Liu, Xue-Yuan
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (11) : 2607 - 2612
  • [30] Visible-light-mediated alkylation of 4-alkyl-1,4-dihydropyridines with alkenyl sulfones
    Yue, Fuyang
    Dong, Jianyang
    Liu, Yuxiu
    Wang, Qingmin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (41) : 8924 - 8928
12345