Metal-free visible-light-mediated aerobic oxidation of silanes to silanols

被引:22
|
作者
Wang, Jing [1 ]
Li, Bin [1 ]
Liu, Li-Chuan [1 ]
Jiang, Chenran [1 ]
He, Tao [1 ]
He, Wei [1 ]
机构
[1] Tsinghua Univ, Sch Pharmaceut Sci, Beijing 100084, Peoples R China
基金
国家重点研发计划; 中国国家自然科学基金;
关键词
metal-free; photoredox; aerobic oxidation; silanes; MERGING PHOTOREDOX CATALYSIS; DIRECTING GROUP; SINGLET OXYGEN; HYDROGEN; AROMATIZATION; ORGANOSILANES; ALKENYLATION; GENERATION; PRODUCT; OXIDANT;
D O I
10.1007/s11426-018-9289-9
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Oxidation of silanes into silanols using water/air has attracted considerable attention. The known methods with no exception required a metal catalyst. Herein we report the first metal-free method: 2 mol% Rose Bengal as the catalyst, air (O-2) as the oxidant, water as the additive and under visible light irradiation. While this method produces various silanols in a simple, cost-effective, efficient (92%-99% yields) and scalable fashion, its reaction mechanism is very different than the reported ones associated with metal catalysis.
引用
收藏
页码:1594 / 1599
页数:6
相关论文
共 50 条
  • [41] Fluoroalkylselenolation of Alkyl Silanes/Trifluoroborates under Metal-Free Visible-Light Photoredox Catalysis
    Ghiazza, Clement
    Khrouz, Lhoussain
    Billard, Thierry
    Monnereau, Cyrille
    Tlili, Anis
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (10) : 1559 - 1566
  • [42] Visible-Light-Mediated Metal-Free Hydrosilylation of Alkenes through Selective Hydrogen Atom Transfer for Si-H Activation
    Zhou, Rong
    Goh, Yi Yiing
    Liu, Haiwang
    Tao, Hairong
    Li, Lihua
    Wu, Jie
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (52) : 16621 - 16625
  • [43] Simple Benchtop Approach to Polymer Brush Nanostructures Using Visible-Light-Mediated Metal-Free Atom Transfer Radical Polymerization
    Discekici, Emre H.
    Pester, Christian W.
    Treat, Nicolas J.
    Lawrence, Immy
    Mattson, Kaila M.
    Narupai, Benjaporn
    Toumayan, Edward P.
    Luo, Yingdong
    McGrath, Alaina J.
    Clark, Paul G.
    de Alaniz, Javier Read
    Hawker, Craig J.
    ACS MACRO LETTERS, 2016, 5 (02) : 258 - 262
  • [44] Visible-light-mediated metal-free regioselective oxidative C-C bond cleavage of lignin dimers to aromatic acids
    Meng, Ye
    Li, Jie
    Liu, Huan
    Wu, Hongguo
    Li, Hu
    CHEMICAL COMMUNICATIONS, 2024, 60 (12) : 1642 - 1645
  • [45] Metal-Free Visible-Light-Mediated Desulfurization and Aromatization of Dihydropyrimidine-2-thiones for Synthesis of 2-Unsubstituted Pyrimidines
    Yang, Tian-Yao
    Wang, Xi-Cun
    Quan, Zheng-Jun
    SYNLETT, 2017, 28 (07) : 847 - 850
  • [46] Visible-light-mediated decarboxylative (E)-alkenylation of aliphatic carboxylic acids with aryl styryl sulfones under metal-free conditions
    Burlingham, Sarah-Jayne
    Guijarro, David
    Bosque, Irene
    Chinchilla, Rafael
    Gonzalez-Gomez, Jose C.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (40) : 7923 - 7928
  • [47] Metal-free aerobic oxidation of benzazole derivatives
    Dos Santos, Aurelie
    El Kaim, Laurent
    Grimaud, Laurence
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (20) : 3282 - 3287
  • [48] Visible-Light-Mediated Aminoquinolate Diarylboron-Catalyzed Metal-Free Hydroxylation of Organoboronic Acids under Air and Room Temperature
    Wei, Lanfeng
    Zhang, Jinli
    Xu, Liang
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2020, 8 (37) : 13894 - 13899
  • [49] Visible-light-mediated oxidative arylation of vinylarenes under aerobic conditions
    Bu, Meijie
    Niu, Teng Fei
    Cai, Chun
    CATALYSIS SCIENCE & TECHNOLOGY, 2015, 5 (02) : 830 - 834
  • [50] Visible-light-driven metal-free aerobic synthesis of highly diastereoselective phosphinoylpyrroloindoles
    Gorre, Ramesh
    Enagandhula, Damodar
    Balasubramanian, Sridhar
    Akondi, Srirama Murthy
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (07) : 1354 - 1358