Organophotocatalytic oxidation of alcohols to carboxylic acids

被引:10
|
作者
Tambe, Shrikant D. [1 ]
Cho, Eun Jin [1 ]
机构
[1] Chung Ang Univ, Dept Chem, 84 Heukseok Ro, Seoul 156756, South Korea
基金
新加坡国家研究基金会;
关键词
aerobic oxidation; alcohol; carboxylic acid; photocatalysis; visible light; AEROBIC OXIDATION; SELECTIVE PHOTOOXIDATION; PHOTOREDOX CATALYSIS; AMINES;
D O I
10.1002/bkcs.12610
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A sustainable photochemical protocol for the oxidation of alcohols to ketones and carboxylic acids has been developed by using 2,4,6-triphenylpyrylium tetrafluoroborate (TPPT) as organophotocatalyst and molecular oxygen as oxidant under visible light irradiation. The key reactive oxygen species, superoxide (O-2(center dot-)) for the first oxidation step from alcohol to aldehyde and singlet oxygen (O-1(2)) for the second oxidation step from aldehyde to carboxylic acid, were generated successfully by electron transfer and energy transfer pathways, respectively. A range of primary and secondary alcohols were converted to the corresponding carboxylic acids or ketones, and the optimized reaction conditions were applied to the synthesis of benzocoumarin.
引用
收藏
页码:1226 / 1230
页数:5
相关论文
共 50 条
  • [21] An efficient and practical system for the catalytic oxidation of alcohols, aldehydes, and α,β-unsaturated carboxylic acids
    Grill, Joseph M.
    Ogle, James W.
    Miller, Stephen A.
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (25): : 9291 - 9296
  • [22] Iron Catalysis for Room-Temperature Aerobic Oxidation of Alcohols to Carboxylic Acids
    Ma, Shengming (masm@sioc.ac.cn), 1600, American Chemical Society (138):
  • [23] Oxidation of primary alcohols to carboxylic acids with sodium chlorite catalyzed by TEMPO and bleach
    Zhao, MZ
    Li, J
    Mano, E
    Song, ZG
    Tschaen, DM
    Grabowski, EJJ
    Reider, PJ
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07): : 2564 - 2566
  • [24] Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer
    Tan, Wen-Yun
    Lu, Yi
    Zhao, Jing-Feng
    Chen, Wen
    Zhang, Hongbin
    ORGANIC LETTERS, 2021, 23 (17) : 6648 - 6653
  • [25] OXIDATION OF PRIMARY ALCOHOLS TO CARBOXYLIC-ACIDS AT THE NICKEL-HYDROXIDE ELECTRODE
    KAULEN, J
    SCHAFER, HJ
    SYNTHESIS-STUTTGART, 1979, (07): : 513 - 516
  • [26] Rational Engineering of a Flavoprotein Oxidase for Improved Direct Oxidation of Alcohols to Carboxylic Acids
    Pickl, Mathias
    Winkler, Christoph K.
    Glueck, Silvia M.
    Fraaije, Marco W.
    Faber, Kurt
    MOLECULES, 2017, 22 (12):
  • [27] Transition-metal-free aerobic oxidation of primary alcohols to carboxylic acids
    Wang, Jing
    Liu, Chao
    Yuan, Jiwen
    Lei, Aiwen
    NEW JOURNAL OF CHEMISTRY, 2013, 37 (06) : 1700 - 1703
  • [28] Iron Catalysis for Room-Temperature Aerobic Oxidation of Alcohols to Carboxylic Acids
    Jiang, Xingguo
    Zhang, Jiasheng
    Ma, Shengming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (27) : 8344 - 8347
  • [29] Hydroxymethylaniline Photocages for Carboxylic Acids and Alcohols
    Skalamera, Dani
    Bregovic, Vesna Blazek
    Antol, Ivana
    Bohne, Cornelia
    Basaric, Nikola
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23): : 12554 - 12568
  • [30] Thermal esterification of carboxylic acids with alcohols
    Magerramov, MN
    RUSSIAN JOURNAL OF APPLIED CHEMISTRY, 1995, 68 (02) : 291 - 293