Oxidative C-S Bond Cleavage of Benzyl Thiols Enabled by Visible-Light-Mediated Silver(II) Complexes

被引:21
|
作者
Hong, Boseok [1 ]
Aganda, Kim Christopher C. [2 ]
Lee, Anna [1 ,2 ]
机构
[1] Myongji Univ, Dept Chem, Yongin 17058, South Korea
[2] Myongji Univ, Dept Energy Sci & Technol, Yongin 17058, South Korea
基金
新加坡国家研究基金会;
关键词
SINGLET MOLECULAR-OXYGEN; PHOTOSENSITIZED OXIDATION; PHOTOREDOX CATALYSIS; CARBONYL-COMPOUNDS; ORGANIC SULFIDES; SUPEROXIDE ION; SULFOXIDES; MECHANISM; REARRANGEMENT; PERSULFOXIDE;
D O I
10.1021/acs.orglett.0c01399
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The oxidative cleavage reaction of the C-S bond using singlet oxygen is challenging because of its uncontrollable nature. We have developed a novel method for the singlet-oxygen-mediated selective C-S bond cleavage reaction using silver(II)-ligand complexes. Visible-light-induced silver catalysis enables the controlled oxidative cleavage of benzyl thiols to afford carbonyl compounds, such as aldehydes or ketones, which are important synthetic components.
引用
收藏
页码:4395 / 4399
页数:5
相关论文
共 50 条
  • [1] Visible-light-mediated oxidative C-S bond cleavage of benzyl thiols through in situ activation strategy
    Hong, Boseok
    Lee, Anna
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (30) : 5938 - 5942
  • [2] Visible-Light-Mediated Photocatalytic Oxidative C-C Bond Cleavage of Geminal Diazides: An Approach to Oxamates
    Katta, Narenderreddy
    Murugan, Arumugavel
    Sharma, Sonika
    Sharada, Duddu S.
    SYNOPEN, 2021, 05 (02): : 152 - 157
  • [3] Visible-light-mediated C-S bond activation in cysteine derivatives with quinoxalinones for the synthesis of heteroaryl amino acids
    Ling, Shuqi
    Hai, Jingjie
    Li, Xinyao
    ORGANIC CHEMISTRY FRONTIERS, 2025, 12 (06): : 2018 - 2024
  • [4] Visible-light-mediated C-F bond cleavage for the synthesis of polyfluorinated compounds
    Wang, Bin
    Wang, Cui-Tian
    Li, Xue-Song
    Sun, Wen-Hui
    Liu, Xue-Yuan
    Liang, Yong-Min
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (13) : 3341 - 3346
  • [5] 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
  • [6] Recent Progress in the C-S Bond Formation Reactions Mediated by Visible Light
    Wu Mina
    Liu Bo
    Yuan Jialong
    Fu Qiang
    Wang Rui
    Lou Dawei
    Liang Fushun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (07) : 2269 - 2292
  • [7] γ-Functionalizations of Amines through Visible-Light-Mediated, Redox-Neutral C-C Bond Cleavage
    Shu, Wei
    Genoux, Alexandre
    Li, Zhaodong
    Nevado, Cristina
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (35) : 10521 - 10524
  • [8] Direct synthesis of hydrazones by visible light mediated aerobic oxidative cleavage of the C=C bond
    Ding, Ya
    Li, Hao
    Meng, Yunge
    Zhang, Te
    Li, Jiawen
    Chen, Qiu-Yun
    Zhu, Chunyin
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (08): : 1611 - 1614
  • [9] Thiolate Coordination vs C-S Bond Cleavage of Thiolates in Dinickel(II) Complexes
    Das, Ayan
    Ganguly, Tuhin
    Majumdar, Amit
    INORGANIC CHEMISTRY, 2021, 60 (02) : 945 - 959
  • [10] C=C Bond Oxidative Cleavage of BODIPY Photocages by Visible Light
    Xu, Youwei
    Lin, Shanmeng
    He, Rongkun
    Zhang, Yichuan
    Gao, Quan
    Ng, Dennis K. P.
    Geng, Jin
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (44) : 11268 - 11272