Visible-light-promoted organic dye catalyzed perfluoroalkylation of hydrazones under mild conditions

被引:17
|
作者
Zhou, Ming-Dong [1 ]
Peng, Zhen [1 ]
Li, Lei [1 ]
Wang, He [1 ]
机构
[1] Liaoning Shihua Univ, Sch Chem & Mat Sci, Dandong Rd 1, Fushun 113001, Peoples R China
基金
中国国家自然科学基金;
关键词
Visible-light photoredox catalysis; Eosin Y; Perfluoroalkylation; Hydrazones; C-H TRIFLUOROMETHYLATION; PHOTOREDOX CATALYSIS; RADICAL TRIFLUOROMETHYLATION; FLUOROALKYLATION REACTIONS; UNACTIVATED ALKENES; FLUORINE; IODIDES; DIFLUOROALKYLATION; PHARMACEUTICALS; ISOCYANIDES;
D O I
10.1016/j.tetlet.2019.151124
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general and facile visible-light-promoted organic dye catalyzed perfluoroalkylation of hydrazones has been developed using inexpensive and non-toxic Eosin Y as the photoredox catalyst under mild conditions. This reaction protocol exhibits synthetic simplicity, broad scope of substrates, and excellent functional group compatibility. A gram scale synthesis can be also facilitated with a satisfactory yield, which opens up the possibility of practical applications. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页数:4
相关论文
共 50 条
  • [1] Visible-light-promoted direct C3-trifluoromethylation and perfluoroalkylation of imidazopyridines
    Li, Meichen
    Li, Gaolin
    Dai, Chenxun
    Zhou, Wenjun
    Zhan, Wenqiang
    Gao, Muyang
    Rong, Yuan
    Tan, Ze
    Deng, Wei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (38) : 8301 - 8306
  • [2] Visible-light-promoted organic-dye-catalyzed three-component coupling of aldehydes, hydrazines and bromodifluorinated reagents
    Li, Jin-Xue
    Li, Lei
    Zhou, Ming-Dong
    Wang, He
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (06): : 1003 - 1007
  • [3] Visible-light-promoted organic dye-catalyzed sulfidation and phosphorylation of arylhydrazines toward aromatic sulfides and diarylphosphoryl hydrazides
    Li, Rui
    Shi, Tao
    Chen, Xiao-Lan
    Lv, Qi-Yan
    Zhang, Yin-Li
    Peng, Yu-Yu
    Qu, Ling-Bo
    Yu, Bing
    NEW JOURNAL OF CHEMISTRY, 2019, 43 (34) : 13642 - 13646
  • [4] Visible-light-promoted organic-dye-catalyzed sulfonylation/cyclization to access indolo[2,1-a]isoquinoline derivatives
    Tang, Yucai
    Duan, Jinglin
    Yang, Biyu
    He, Yupeng
    Du, Changyuan
    Zhang, Xiangyang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (40) : 8152 - 8161
  • [5] A Visible-Light-Promoted Metal-Free Strategy towards Arylphosphonates: Organic-Dye-Catalyzed Phosphorylation of Arylhydrazines with Trialkylphosphites
    Li, Rui
    Chen, Xiaolan
    Wei, Shengkai
    Sun, Kai
    Fan, Lulu
    Liu, Yan
    Qu, Lingbo
    Zhao, Yufen
    Yu, Bing
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (24) : 4807 - 4813
  • [6] Visible-light-promoted catalytic epoxidation of alkenes under metal-free conditions
    Tan, Dabao
    Cai, Xiaoyan
    Zhang, Lele
    Liu, Boyu
    Zeng, Jianbin
    Li, Feiming
    Cai, Zhixiong
    Huang, Mingqiang
    Chen, Xiaoping
    Cai, Shunyou
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (22): : 6437 - 6443
  • [7] Visible-light mediated directed perfluoroalkylation of hydrazones
    Ji, Heng
    Ni, Hui-qiong
    Zhi, Peng
    Xi, Zi-wei
    Wang, Wei
    Shi, Jian-jun
    Shen, Yong-miao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (28) : 6014 - 6023
  • [8] Visible-Light-Promoted Efficient Aerobic Dehydrogenation of N-Heterocycles by a Tiny Organic Semiconductor Under Ambient Conditions
    Yu, Kunyi
    Zhang, Hanjie
    Su, Chenliang
    Zhu, Yongfa
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (13) : 1956 - 1960
  • [9] Visible-light-promoted synthesis of diaryl sulfides under air
    Hong, Boseok
    Lee, Juyoung
    Lee, Anna
    TETRAHEDRON LETTERS, 2017, 58 (29) : 2809 - 2812
  • [10] Visible-Light-Promoted Selenofunctionalization of Alkenes
    Conner, Elizabeth S.
    Crocker, Katherine E.
    Fernando, Ranelka G.
    Fronczek, Frank R.
    Stanley, George G.
    Ragains, Justin R.
    ORGANIC LETTERS, 2013, 15 (21) : 5558 - 5561