4CzIPN catalyzed photochemical oxidation of benzylic alcohols

被引:13
作者
Zhang, Heng [1 ]
Guo, Tianyun [1 ]
Wu, Mingzhong [2 ]
Huo, Xing [2 ]
Tang, Shouchu [1 ]
Wang, Xiaolei [2 ]
Liu, Jian [1 ]
机构
[1] Lanzhou Univ, Sch Pharm, Lanzhou 730000, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
关键词
Photocatalysts; Oxidation; Air; Benzylic alcohols;
D O I
10.1016/j.tetlet.2021.152878
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A green photoredox oxidation of benzylic primary and secondary alcohols to aldehydes and ketones with air as an oxidant was reported. The oxidation shows broad substrate scope and excellent selectivity over benzylic alcohols to the aliphatic alcohols. Further mechanistic studies revealed a quinuclidine mediated HAT process, and blue LEDs promoted 4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene) photoredox cycle were involved in our oxidation. (C) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数:4
相关论文
共 42 条
  • [1] Selective oxidation of secondary alcohols
    Arterburn, JB
    [J]. TETRAHEDRON, 2001, 57 (49) : 9765 - 9788
  • [2] Visible-Light-Activated C-C Bond Cleavage and Aerobic Oxidation of Benzyl Alcohols Employing BiMXO5(M=Mg, Cd, Ni, Co, Pb, Ca and X=V, P)
    Bhim, Anupam
    Sasmal, Shreya
    Gopalakrishnan, Jagannatha
    Natarajan, Srinivasan
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (19) : 3104 - 3115
  • [3] Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis
    Capaldo, Luca
    Ravelli, Davide
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (15) : 2056 - 2071
  • [4] Singlet Oxygen-Engaged Selective Photo-Oxidation over Pt Nanocrystals/Porphyrinic MOF: The Roles of Photothermal Effect and Pt Electronic State
    Chen, Yu-Zhen
    Wang, Zhiyong U.
    Wang, Hengwei
    Lu, Junling
    Yu, Shu-Hong
    Jiang, Hai-Long
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (05) : 2035 - 2044
  • [5] Catalytic photooxidation of 4-methoxybenzyl alcohol with a flavin-zinc(II)-cyclen complex
    Cibulka, R
    Vasold, R
    König, B
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (24) : 6223 - 6231
  • [6] Site-Selective and Stereoselective C-H Alkylations of Carbohydrates via Combined Diarylborinic Acid and Photoredox Catalysis
    Dimakos, Victoria
    Su, Hsin Y.
    Garrett, Graham E.
    Taylor, Mark S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (13) : 5149 - 5153
  • [7] Oxidation of alkyl benzenes by a flavin photooxidation catalyst on nanostructured metal-oxide films
    Dongare, Prateek
    MacKenzie, Ian
    Wang, Degao
    Nicewicz, David A.
    Meyer, Thomas J.
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2017, 114 (35) : 9279 - 9283
  • [8] Efficient catalysis of rare-earth metal ions in photoinduced electron-transfer oxidation of benzyl alcohols by a flavin analogue
    Fukuzumi, S
    Yasui, K
    Suenobu, T
    Ohkubo, K
    Fujitsuka, M
    Ito, O
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2001, 105 (46) : 10501 - 10510
  • [9] Photocatalytic Oxidation of Alcohols over TiO2 Covered with Nb2O5
    Furukawa, Shinya
    Shishido, Tetsuya
    Teramura, Kentaro
    Tanaka, Tsunehiro
    [J]. ACS CATALYSIS, 2012, 2 (01): : 175 - 179
  • [10] Using Singlet Oxygen to Synthesize Natural Products and Drugs
    Ghogare, Ashwini A.
    Greer, Alexander
    [J]. CHEMICAL REVIEWS, 2016, 116 (17) : 9994 - 10034