Aerobic Oxidative Sulfenylation of Pyrazolones and Pyrazoles Catalyzed by Metal-Free Flavin-Iodine Catalysis

被引:38
|
作者
Tanimoto, Kazumasa [1 ]
Ohkado, Ryoma [1 ]
Iida, Hiroki [1 ]
机构
[1] Shimane Univ, Grad Sch Nat Sci & Technol, Dept Chem, 1060 Nishikawatsu, Matsue, Shimane 6908504, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 22期
关键词
BOND FORMATION; C-S; THIOLATION; SULPHENYLATION; TEMPERATURE; INDOLES; ANALOGS; THIOLS; POTENT;
D O I
10.1021/acs.joc.9b02422
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two-component metal-free catalytic oxidative sulfenylation of pyrazolones with thiols has been achieved using the biomimetic flavin and iodine. The methodology is mild and eco-friendly, proceeds in the presence of air or molecular oxygen (1 atm) as the sole sacrificial reagent, and generates water as the only byproduct. The methodology was also extended to the sulfenylation of pyrazoles and electron-rich benzenes and afforded a series of thioethers in good yields.
引用
收藏
页码:14980 / 14986
页数:7
相关论文
共 50 条
  • [1] Flavin-iodine coupled organocatalysis for the aerobic oxidative direct sulfenylation of indoles with thiols under mild conditions
    Ohkado, Ryoma
    Ishikawa, Tatsuro
    Iida, Hiroki
    GREEN CHEMISTRY, 2018, 20 (05) : 984 - 988
  • [2] Metal-free direct construction of sulfenylated pyrazoles via the NaOH promoted sulfenylation of pyrazolones with aryl thiols
    Liu, Xiaoxia
    Cui, Huanhuan
    Yang, Daoshan
    Dai, Shicui
    Zhang, Tiantian
    Sun, Jingyu
    Wei, Wei
    Wang, Hua
    RSC ADVANCES, 2016, 6 (57) : 51830 - 51833
  • [3] Metal-free, iodine-catalyzed regioselective sulfenylation of indoles with thiols
    Yi, Shanli
    Li, Meichao
    Mo, Weimin
    Hu, Xinquan
    Hu, Baoxiang
    Sun, Nan
    Jin, Liqun
    Shen, Zhenlu
    TETRAHEDRON LETTERS, 2016, 57 (17) : 1912 - 1916
  • [4] Metal-Free Atom-Economical Synthesis of Tetra-Substituted Imidazoles via Flavin-Iodine Catalyzed Aerobic Cross-Dehydrogenative Coupling of Amidines and Chalcones
    Takeda, Aki
    Okai, Hayaki
    Watabe, Kyoji
    Iida, Hiroki
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (15): : 10372 - 10376
  • [5] Metal-free molecular iodine-catalyzed direct sulfonylation of pyrazolones with sodium sulfinates leading to sulfonated pyrazoles at room temperature
    Wei, Wei
    Cui, Huanhuan
    Yang, Daoshan
    Liu, Xiaoxia
    He, Chenglong
    Dai, Shicui
    Wang, Hua
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (01): : 26 - 30
  • [6] Tandem Flavin-Iodine-Catalyzed Aerobic Oxidative Sulfenylation of Imidazo[1,2-a]Pyridines with Thiols
    Iida, Hiroki
    Demizu, Ryuta
    Ohkado, Ryoma
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (19): : 12291 - 12296
  • [7] Synthesis of pyrazolones and pyrazoles via Pd-catalyzed aerobic oxidative dehydrogenation
    Zhu, Ye-Fu
    Wei, Bo-Le
    Wei, Jiao-Jiao
    Wang, Wen-Qiong
    Song, Wei-Bin
    Xuan, Li-Jiang
    TETRAHEDRON LETTERS, 2019, 60 (17) : 1202 - 1205
  • [8] Metal-Free Iodine-Catalyzed Synthesis of Fully Substituted Pyrazoles and Its Sulphenylation
    Sun, Jun
    Qiu, Jiang-Kai
    Zhu, Yi-Long
    Guo, Cheng
    Hao, Wen-Juan
    Jiang, Bo
    Tu, Shu-Jiang
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (16): : 8217 - 8224
  • [9] Metal-Free Catalyzed Defluorinative O -Arylation of Pyrazolones with Polyfluoroarenes
    Yang, Liu
    Qin, Tao
    Liu, Bin
    SYNLETT, 2023, 34 (19) : 2336 - 2340
  • [10] Flavin/I2 catalyzed aerobic oxidative C-H sulfenylation of anilines
    Jiang, Xinpeng
    Shen, Zhifeng
    Zheng, Cong
    Fang, Liyun
    Chen, Keda
    Yu, Chuanming
    TETRAHEDRON LETTERS, 2020, 61 (33)