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
  • [1] Visible-light-promoted trifluoromethylselenolation of ortho-hydroxyarylenaminones
    Lu, Linghui
    Zhao, Xiongjie
    Dessie, Wubliker
    Xia, Xianwu
    Duan, Xiangjia
    He, Jun
    Wang, Rui
    Liu, Yu
    Wu, Chao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (08) : 1754 - 1758
  • [2] Synthesis of Monofluoroalkenes through Visible-Light-Promoted Defluorinative Alkylation of gem-Difluoroalkenes with 4-Alkyl-1,4-dihydropyridines
    Du, Hai-Wu
    Sun, Jing
    Gao, Qi-Sheng
    Wang, Jing-Yun
    Wang, He
    Xu, Zhaoqing
    Zhou, Ming-Dong
    ORGANIC LETTERS, 2020, 22 (04) : 1542 - 1546
  • [3] Visible-Light-Promoted Trifluoromethylthiolation of Styrenes by Dual Photoredox/Halide Catalysis
    Honeker, Roman
    Garza-Sanchez, R. Aleyda
    Hopkinson, Matthew N.
    Glorius, Frank
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (13) : 4395 - 4399
  • [4] Visible-Light-Promoted Cross-Coupling Reactions of 4-Alkyl-1,4-dihydropyridines with Thiosulfonate or Selenium Sulfonate: A Unified Approach to Sulfides, Selenides, and Sulfoxides
    Li, Jian
    Yang, Xin-Er
    Wang, Shan-Le
    Zhang, Long-Long
    Zhou, Xiao-Zhou
    Wang, Shun-Yi
    Ji, Shun-Jun
    ORGANIC LETTERS, 2020, 22 (12) : 4908 - 4913
  • [5] Iodocyclization of 1,4-dihydropyridines
    Lavilla, R
    Coll, O
    Nicolàs, M
    Bosch, J
    TETRAHEDRON LETTERS, 1998, 39 (28) : 5089 - 5092
  • [6] PHOTOOXIDATION OF 1,4-DIHYDROPYRIDINES
    MITSUNOBU, O
    WADA, M
    MASUDA, H
    MATSUMOT.S
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1972, 45 (05) : 1453 - +
  • [7] OXIDATION OF 1,4-DIHYDROPYRIDINES
    DUBUR, GY
    ULDRIKIS, YR
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1970, (01): : 83 - &
  • [8] REACTIONS OF 1,4-DIHYDROPYRIDINES
    SAUSINSH, A
    DUBUR, G
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1993, (05): : 579 - 612
  • [9] REACTIONS OF 1,4-DIHYDROPYRIDINES
    SAUSINS, A
    DUBURS, G
    HETEROCYCLES, 1988, 27 (01) : 291 - 314
  • [10] ZINC(II)-PROMOTED REDUCTION OF KETONES BY 1-METHYL-1,4-DIHYDROPYRIDINES
    DEKONING, AJ
    ALBERTSJANSEN, HJ
    BOERSMA, J
    VANDERKERK, GJM
    RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1980, 99 (10): : 316 - 321
12345