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
  • [41] Visible-Light-Mediated Sulfonylimination of Tertiary Amines with Sulfonylazides Involving Csp3-Csp3 Bond Cleavage
    Gui, Jiao
    Xie, Haisheng
    Jiang, Huanfeng
    Zeng, Wei
    ORGANIC LETTERS, 2019, 21 (08) : 2804 - 2807
  • [42] Visible-Light Mediated, Photocatalyst-Free C-S Bond Formation via EDA Complex Formation
    Shanthi., Markabandhu
    Perumal, Karuppaiah
    Hemamalini, Vijayakumar
    Dandela, Rambabu
    Ramesh, Subburethinam
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 14 (03)
  • [43] Recent application of visible-light induced radicals in C-S bond formation
    Srivastava, Vishal
    Singh, Pravin K.
    Srivastava, Arjita
    Singh, Praveen P.
    RSC ADVANCES, 2020, 10 (34) : 20046 - 20056
  • [44] Eosin Y catalyzed visible light mediated aerobic photo-oxidative cleavage of the C-C double bond of styrenes
    Singh, Atul K.
    Chawla, Ruchi
    Yadav, La Dhar S.
    TETRAHEDRON LETTERS, 2015, 56 (05) : 653 - 656
  • [45] Oxidative C-C Bond Cleavage of Aldehydes via Visible-Light Photoredox Catalysis
    Sun, Hongnan
    Yang, Chao
    Gao, Fei
    Li, Zhe
    Xia, Wujiong
    ORGANIC LETTERS, 2013, 15 (03) : 624 - 627
  • [46] Visible-Light-Induced Cleavage of C-S Bonds in Thioacetals and Thioketals with Iodine as a Photocatalyst
    Krumb, Matthias
    Kammer, Lisa Marie
    Forster, Robert
    Grundke, Caroline
    Opatz, Till
    CHEMPHOTOCHEM, 2020, 4 (02): : 101 - 104
  • [47] Visible-light-mediated amidation from carboxylic acids and tertiary amines via C-N cleavage
    Gu, Chengyihan
    Wang, Shuaishuai
    Zhang, Qingran
    Xie, Jin
    CHEMICAL COMMUNICATIONS, 2022, 58 (39) : 5873 - 5876
  • [48] Simultaneous Construction of C-Se And C-S Bonds via the Visible-Light-Mediated Multicomponent Cascade Reaction of Diselenides, Alkynes, and SO2
    Chen, Hui
    Ding, Rui
    Tang, Haitao
    Pan, Yingming
    Xu, Yanli
    Chen, Yanyan
    CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (19) : 3264 - 3268
  • [50] Syntheses, Crystal Structures and Cleavage Mechanism of C-S Bond in Cd(II) and Zn(II) Complexes with Tris(2-mercaptopyridyl)methane
    Yang Hong
    Han Xin-Li
    CHINESE JOURNAL OF INORGANIC CHEMISTRY, 2015, 31 (08) : 1597 - 1602