Visible Light-Mediated Selective Aerobic Oxidation of Alcohols Catalyzed by Disulfide in Batch and Flow

被引：1
|
作者：
Lu, Yue [1 ]
Zhao, Jingnan [1 ]
Sun, Huinan [1 ]
Li, Jianing [1 ]
Yu, Zongyi [1 ]
Ma, Cunfei [1 ]
Zhu, Hongfei [1 ]
Meng, Qingwei [1 ,2 ]
机构：
[1] Dalian Univ Technol, Sch Chem Engn, Dept Pharmaceut Engn, State Key Lab Fine Chem, Dalian 116024, Peoples R China
[2] Dalian Univ Technol, Ningbo Inst, Ningbo 315000, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 06期
基金：
中国国家自然科学基金;
关键词：
THIYL-RADICAL CATALYST; TRANSITION-METAL-FREE; PHOTOCATALYTIC OXIDATION; ALKENES; SYSTEM;
D O I：
10.1021/acs.joc.3c02718
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Selective aerobic oxidation of alcohols in batch and flow can be realized under light irradiation, utilizing disulfide as the photocatalyst, and a variety of primary and secondary alcohols were converted to the corresponding aldehydes or ketones in up to 99% yield and high selectivity. The reaction efficiency could be increased even further by combining a continuous-flow strategy. Detailed mechanistic studies have also been achieved to determine the role of oxygen and disulfides in this oxidation.
引用
收藏
页码：3868 / 3874
页数：7
相关论文
共 50 条
  • [41] Visible Light-Mediated Copper(I)-Catalysed Aerobic Oxidation of Ynamides/Ynamines at Room Temperature: A Sustainable Approach to the Synthesis of α-Ketoimides/α-Ketoamides
    Ragupathi, Ayyakkannu
    Charpe, Vaibhav Pramod
    Sagadevan, Arunachalam
    Hwang, Kuo Chu
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (07) : 1138 - 1143
  • [42] Light-Mediated Formal Radical Deoxyfluorination of Tertiary Alcohols through Selective Single-Electron Oxidation with TEDA2+.
    Troyano, Francisco Jose Aguilar
    Ballaschk, Frederic
    Jaschinski, Marcel
    Oezkaya, Yasemin
    Gomez-Suarez, Adrian
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (62) : 14054 - 14058
  • [43] Aerobic oxidation of alcohols with air catalyzed by decacarbonyldimanganese
    Meng, Shan-Shui
    Lin, Li-Rong
    Luo, Xiang
    Lv, Hao-Jun
    Zhao, Jun-Ling
    Chan, Albert S. C.
    GREEN CHEMISTRY, 2019, 21 (22) : 6187 - 6193
  • [44] Bromine-Catalyzed Aerobic Oxidation of Alcohols
    Uyanik, Muhammet
    Fukatsu, Ryota
    Ishihara, Kazuaki
    CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (03) : 456 - 460
  • [45] Visible-Light-Driven Enantioselective Aerobic Oxidation of β-Dicarbonyl Compounds Catalyzed by Cinchona-Derived Phase Transfer Catalysts in Batch and Semi-Flow
    Tang, Xiao-Fei
    Zhao, Jing-Nan
    Wu, Yu-Feng
    Feng, Shi-Hao
    Yang, Fan
    Yu, Zong-Yi
    Meng, Qing-Wei
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (22) : 5245 - 5252
  • [46] Light-Mediated Polymerization Catalyzed by Carbon Nanomaterials
    Luo, Xiongfei
    Zhai, Yingxiang
    Wang, Ping
    Tian, Bing
    Liu, Shouxin
    Li, Jian
    Yang, Chenhui
    Strehmel, Veronika
    Li, Shujun
    Matyjaszewski, Krzysztof
    Yilmaz, Gorkem
    Strehmel, Bernd
    Chen, Zhijun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (18)
  • [47] Light-Mediated Deoxygenation of Alcohols with a Dimeric Gold Catalyst
    McCallum, Terry
    Slavko, Ekaterina
    Morin, Mathieu
    Barriault, Louis
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (01) : 81 - 85
  • [48] Mild oxidation of benzyl alcohols to benzyl aldehydes or ketones catalyzed by visible light
    Ren, Shujian
    Cheng, Dongping
    Li, Xiaonian
    Xu, Xiaoliang
    TETRAHEDRON LETTERS, 2021, 76
  • [49] Selective Aerobic Oxidation of Benzylic Alcohols Catalyzed by a Dicyclopropenylidene-Ag(I) Complex
    Mir, Roya
    Rowshanpour, Rozhin
    Dempsey, Katie
    Pilkington, Melanie
    Dudding, Travis
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (09): : 5726 - 5731
  • [50] Selective Aerobic Oxidation of Benzylic Alcohols Catalyzed by Carbon-Based Catalysts: A Nonmetallic Oxidation System
    Kuang, Yongbo
    Islam, Nazrul M.
    Nabae, Yuta
    Hayakawa, Teruaki
    Kakimoto, Masa-aki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (02) : 436 - 440
12345