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
来源：
BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2022年 / 43卷 / 11期
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
  • [11] Copper-catalyzed aerobic oxidation of primary alcohols to carboxylic acids
    Yu, Yibo
    Zhai, Di
    Zhou, Zhengnan
    Jiang, Sheng
    Qian, Hui
    Ma, Shengming
    CHEMICAL COMMUNICATIONS, 2023, 59 (35) : 5281 - 5284
  • [12] ON ESTERIFICATION OF CARBOXYLIC ACIDS WITH ALCOHOLS
    Baiyramova, Z. E.
    Magerramov, A. M.
    Magerramov, M. N.
    Aliev, I. A.
    Lyutfaliev, A. G.
    Garazade, Kh. A.
    IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA I KHIMICHESKAYA TEKHNOLOGIYA, 2012, 55 (01): : 115 - +
  • [13] Electrochemical oxidation of alcohols and carboxylic acids with diamond anodes - A comparison with other advanced oxidation processes
    Canizares, P.
    Paz, R.
    Saez, C.
    Rodrigo, M. A.
    ELECTROCHIMICA ACTA, 2008, 53 (05) : 2144 - 2153
  • [14] Carbon-carbon bond fission on oxidation of primary alcohols to carboxylic acids
    Bekish, Andrei V.
    TETRAHEDRON LETTERS, 2012, 53 (24) : 3082 - 3085
  • [15] A Recyclable, Metal-Free Mechanochemical Approach for the Oxidation of Alcohols to Carboxylic Acids
    Denlinger, Kendra Leahy
    Carr, Preston
    Waddell, Daniel C.
    Mack, James
    MOLECULES, 2020, 25 (02):
  • [16] Cobalt(II)-catalyzed oxidation of alcohols into carboxylic acids and ketones with hydrogen peroxide
    Das, S
    Punniyamurthy, T
    TETRAHEDRON LETTERS, 2003, 44 (32) : 6033 - 6035
  • [17] Combining photoredox catalysis and oxoammonium cations for the oxidation of aromatic alcohols to carboxylic acids
    Nandi, Jyoti
    Hutcheson, Ellen L.
    Leadbeater, Nicholas E.
    TETRAHEDRON LETTERS, 2021, 63
  • [18] Carboxylic acids from primary alcohols and aldehydes by a pyridinium chlorochromate catalyzed oxidation
    Hunsen, M
    SYNTHESIS-STUTTGART, 2005, (15): : 2487 - 2490
  • [19] IBX-mediated oxidation of primary alcohols and aldehydes to form carboxylic acids
    Mazitschek, R
    Mülbaier, M
    Giannis, A
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (21) : 4059 - 4061
  • [20] 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
12345