Visible-Light-Induced Beckmann Rearrangement by Organic Photoredox Catalysis

被引:30
|
作者
Tang, Li [1 ]
Wang, Zhi-Lv [1 ]
Wan, Hai-Lan [1 ]
He, Yan-Hong [1 ]
Guan, Zhi [1 ]
机构
[1] Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China
基金
中国国家自然科学基金;
关键词
BOND FORMATION; KETOXIMES; MILD; LACTAMS; OXIMES; AMIDES;
D O I
10.1021/acs.orglett.0c02168
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and general strategy for efficient direct conversion of oximes to amides using an inexpensive organic photocatalyst and visible light is described. This radical Beckmann rearrangement can be performed under mild conditions. Various alkyl aryl ketoximes and diaryl ketoximes can be effectively converted into the corresponding amides in excellent yields.
引用
收藏
页码:6182 / 6186
页数:5
相关论文
共 50 条
  • [1] Visible-Light-Induced Photoredox Catalysis with a TetraceriumContaining Silicotungstate**
    Suzuki, Kosuke
    Tang, Fei
    Kikukawa, Yuji
    Yamaguchi, Kazuya
    Mizuno, Noritaka
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (21) : 5356 - 5360
  • [2] Visible-light-induced [4+2] cycloaddition of pentafulvenes by organic photoredox catalysis
    Tanaka, Kenta
    Asada, Yosuke
    Hoshino, Yujiro
    Honda, Kiyoshi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (40) : 8074 - 8078
  • [3] Iron Photoredox Catalysis as an Effective Tool for Organic Synthesis via Visible-Light-Induced Homolysis (VLIH)
    Srivastava, Vishal
    Singh, Praveen P.
    Sinha, Surabhi
    Tivari, Shraddha
    Singh, Pravin K.
    CHEMISTRYSELECT, 2025, 10 (04):
  • [4] Visible-light-induced hydroalkoxymethylation of electron-deficient alkenes by photoredox catalysis
    Miyazawa, Kazuki
    Yasu, Yusuke
    Koike, Takashi
    Akita, Munetaka
    CHEMICAL COMMUNICATIONS, 2013, 49 (65) : 7249 - 7251
  • [5] Visible-Light-Induced Regioselective Deaminative Alkylation of Coumarins via Photoredox Catalysis
    Tao, Maoling
    Wang, An-Jun
    Guo, Peng
    Li, Weipiao
    Zhao, Liang
    Tong, Jie
    Wang, Haoyang
    Yu, Yanbo
    He, Chun-Yang
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (01) : 24 - 29
  • [6] Visible-Light-Induced Photoredox Catalysis: An Easy Access to Green Radical Chemistry
    Koike, Takashi
    Akita, Munetaka
    SYNLETT, 2013, 24 (19) : 2492 - 2505
  • [7] Visible-Light-Induced Photoredox Catalysis of Dye-Sensitized Titanium Dioxide: Selective Aerobic Oxidation of Organic Sulfides
    Lang, Xianjun
    Zhao, Jincai
    Chen, Xiaodong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (15) : 4697 - 4700
  • [8] Visible-light-induced synthesis of a variety of trifluoromethylated alkenes from potassium vinyltrifluoroborates by photoredox catalysis
    Yasu, Yusuke
    Koike, Takashi
    Akita, Munetaka
    CHEMICAL COMMUNICATIONS, 2013, 49 (20) : 2037 - 2039
  • [9] Recent Synthetic Applications of the Hypervalent Iodine(III) Reagents in Visible-Light-Induced Photoredox Catalysis
    Chen, Chaoyue
    Wang, Xin
    Yang, Tinghai
    FRONTIERS IN CHEMISTRY, 2020, 8
  • [10] Photocatalytic oxidation of lignin model systems by merging palladium and visible-light-induced photoredox catalysis
    Kaerkaes, Markus
    Matsuura, Bryan
    Stephenson, Corey
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250