Electrochemical trifluoromethylation of 2-isocyanobiaryls using CF3SO2Na: synthesis of 6-(trifluoromethyl)phenanthridines

被引:9
|
作者
La-ongthong, Kannika [1 ,2 ]
Chantarojsiri, Teera [1 ,2 ]
Soorukram, Darunee [1 ,2 ]
Leowanawat, Pawaret [1 ,2 ]
Reutrakul, Vichai [1 ,2 ]
Kuhakarn, Chutima [1 ,2 ]
机构
[1] Mahidol Univ, Fac Sci, Dept Chem, Rama 6 Rd, Bangkok 10400, Thailand
[2] Mahidol Univ, Fac Sci, Ctr Excellence Innovat Chem PERCH CIC, Rama 6 Rd, Bangkok 10400, Thailand
关键词
D O I
10.1039/d3ob00239j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient trifluoromethylation of 2-isocyanobiaryls was developed through the constant current electrolysis, employing sodium trifluoromethanesulfinate (CF3SO2Na) as the trifluoromethyl source. The method enabled the syntheses of a series of 6-(trifluoromethyl)phenanthridine derivatives in moderate to high yields under metal- and oxidant-free conditions. A gram-scale synthesis highlights the synthetic versatility of the reported protocol.
引用
收藏
页码:4225 / 4236
页数:13
相关论文
共 50 条
  • [1] Electrochemical Decarboxylative Trifluoromethylation of , -Unsaturated Carboxylic Acids with CF3SO2Na
    Li, Fang-Yuan
    Lin, Dian-Zhao
    He, Tian-Jun
    Zhong, Wei-Qiang
    Huang, Jing-Mei
    CHEMCATCHEM, 2019, 11 (09) : 2350 - 2354
  • [2] Electrochemical Oxidative Trifluoromethylation of α-Oxoketene Ketene Dithioacetals with CF3SO2Na
    Gu, Qingyun
    Cheng, Zhenfeng
    Zeng, Xiaobao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (05) : 1537 - 1544
  • [3] Oxidative Trifluoromethylation of CF3SO2Na with Olefins Mediated by Diacetyl
    Xu, Wenyi
    Feng, Yisi
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2020, 41 (07): : 1567 - 1574
  • [4] External-Oxidant-Free Electrochemical Oxidative Trifluoromethylation of Arenes Using CF3SO2Na as the CF3 Source
    Deng, Yong
    Lu, Fangling
    You, Siqi
    Xia, Tianrui
    Zheng, Yifan
    Lu, Cuifen
    Yang, Guichun
    Chen, Zuxing
    Gao, Meng
    Lei, Aiwen
    CHINESE JOURNAL OF CHEMISTRY, 2019, 37 (08) : 817 - 820
  • [5] Electrochemically mediated trifluoromethylation of 2H-indazole derivatives using CF3SO2Na
    Wei, Tingting
    Wang, Kai
    Yu, Zhichen
    Hou, Jiahao
    Xie, Yuanyuan
    TETRAHEDRON LETTERS, 2021, 86
  • [6] Copper-catalyzed trifluoromethylation of styrene derivatives with CF3SO2Na
    Wu, Liu-Hai
    Zhao, Kai
    Shen, Zhi-Liang
    Loh, Teck-Peng
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (09): : 1872 - 1875
  • [7] Silver(I)-catalyzed denitrative trifluoromethylation of β-nitrostyrenes with CF3SO2Na
    Huang, Ping
    Li, Yaming
    Fu, Xinmei
    Zhang, Rong
    Jin, Kun
    Wang, Wenxin
    Duan, Chunying
    TETRAHEDRON LETTERS, 2016, 57 (42) : 4705 - 4708
  • [8] Photoinduced synthesis of -trifluoromethylated ketones through the oxidative trifluoromethylation of styrenes using CF3SO2Na as a trifluoromethyl reagent without an external photoredox catalyst
    Zhao, Lulu
    Li, Pinhua
    Zhang, Hao
    Wang, Lei
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (01) : 87 - 93
  • [9] UV-Light-Irradiated Trifluoromethylation of Diheteroaryl Disulfides with CF3SO2Na
    Cao, Bao-Qian
    Qiu, Yi-Feng
    Zhang, Xi
    Zhu, Zheng-He
    Quan, Zheng-Jun
    Wang, Xi-Cun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (06) : 1208 - 1214
  • [10] Visible-light-promoted olefinic trifluoromethylation of enamides with CF3SO2Na
    Tang, Kai
    Chen, Yixuan
    Guan, Jianping
    Wang, Zhujun
    Chen, Kai
    Xiang, Haoyue
    Yang, Hua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (34) : 7475 - 7479