Visible-Light-Driven Iodine-Catalyzed Synthesis of Unsymmetrical Disulfides via Oxidative Coupling

被引:1
|
作者
Ren, Ming-Zhe [1 ]
Fu, Yan-Jun [1 ]
Zhang, Bo-Sheng [1 ]
Quan, Zheng-Jun [1 ]
Wang, Xi-Cun [1 ]
机构
[1] Northwest Normal Univ, Coll Chem & Chem Engn, Int Sci & Technol Cooperat Base Water Retent Chem, Lanzhou 730070, Gansu, Peoples R China
来源
SYNTHESIS-STUTTGART | 2023年 / 55卷 / 13期
基金
中国国家自然科学基金;
关键词
iodine; visible light; sulfur; coupling; unsymmetrical disulfides; ONE-POT SYNTHESIS; DISULFANES; ALKENES; ACID;
D O I
10.1055/s-0042-1751433
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, a facile and environmentally friendly oxidative coupling reaction to obtain unsymmetrical disulfide compounds, without using metal or organic dyes as photocatalyst and only using a catalytic amount of iodine, was developed. Oxygen is used as oxidant in the reaction and the substrate scope is wide. A gram-scale synthesis also highlights the synthetic practicality of this photochemical strategy. Moreover, our mechanistic studies support the formation of disulfide products through free-radical coupling.
引用
收藏
页码:2011 / 2018
页数:8
相关论文
共 50 条
  • [1] Iodine-Catalyzed Selective Synthesis of 2-Sulfanylphenols via Oxidative Aromatization of Cyclohexanones and Disulfides
    Ge, Wenlei
    Zhu, Xun
    Wei, Yunyang
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (14-15) : 3014 - 3021
  • [2] Efficient and practical synthesis of unsymmetrical disulfides via base-catalyzed aerobic oxidative dehydrogenative coupling of thiols
    Qiu, Xu
    Yang, Xiaoxue
    Zhang, Yiqun
    Song, Song
    Jiao, Ning
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (13) : 2220 - 2225
  • [3] Nucleophilic disulfurating reagents for unsymmetrical disulfides construction via copper-catalyzed oxidative cross coupling
    Dai, Zhihong
    Xiao, Xiao
    Jiang, Xuefeng
    TETRAHEDRON, 2017, 73 (26) : 3702 - 3706
  • [4] α-Acetoxyarone synthesis via iodine-catalyzed and tert-butyl hydroperoxide-mediateded self-intermolecular oxidative coupling of aryl ketones
    Tan, Liquan
    Chen, Cui
    Liu, Weibing
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 1079 - 1084
  • [5] Alcohol Synthesis by Cobalt-Catalyzed Visible-Light-Driven Reductive Hydroformylation
    MacNeil, Connor S.
    Mendelsohn, Lauren N.
    Pabst, Tyler P.
    Hierlmeier, Gabriele
    Chirik, Paul J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (42) : 19219 - 19224
  • [6] Iodine-catalyzed one-pot synthesis of unsymmetrical meso-substituted porphyrins
    Boens, Benjamin
    Faugeras, Pierre-Antoine
    Vergnaud, Julien
    Lucas, Romain
    Teste, Karine
    Zerrouki, Rachida
    TETRAHEDRON, 2010, 66 (11) : 1994 - 1996
  • [7] Iodine-catalyzed cross-coupling of isocyanides and thiols for the synthesis of S-thiocarbamates
    Pathare, Ramdas S.
    Patil, Vikas
    Kaur, Harpreet
    Maurya, Antim K.
    Agnihotri, Vijai K.
    Khan, Shahnawaz
    Devunuri, Nagaraju
    Sharon, Ashoke
    Sawant, Devesh M.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (37) : 8263 - 8266
  • [8] Synthesis of (Z)-Cinnamate Derivatives via Visible-Light-Driven E-to-Z Isomerization
    Shu, Penghua
    Xu, Haichang
    Zhang, Lingxiang
    Li, Junping
    Liu, Hao
    Luo, Yuehui
    Yang, Xue
    Ju, Zhiyu
    Xu, Zhihong
    SYNOPEN, 2019, 3 (04): : 103 - 107
  • [9] Quinoline Hydroxyalkylations from Iron-Catalyzed, Visible-Light-Driven Decarboxylations
    Rios-Malvaez, Zita G.
    Gonzalez-Rivas, Nelly
    Cuevas-Yanez, Erick
    CATALYSTS, 2024, 14 (12)
  • [10] Iodine-Catalyzed Synthesis of 1,2-Diaryldiketones by Oxidative Cleavage of 1,3-Diaryldiketones with DMSO
    Yuan, Yu
    Zhu, Haitao
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (02) : 329 - 333