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
  • [41] Visible-light-mediated iodine-catalyzed α-hydroxylation of α-methylene ketones under aerobic conditions
    Yang, Jingya
    Xie, Dongtai
    Zhou, Hongyan
    Chen, Shuwen
    Huo, Congde
    Li, Zheng
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (08): : 1325 - 1329
  • [42] Visible-light-driven polymerization towards the green synthesis of plastics
    Lee, Yungyeong
    Boyer, Cyrille
    Kwon, Min Sang
    NATURE REVIEWS MATERIALS, 2022, 7 (02) : 74 - 75
  • [43] Visible-light-driven polymerization towards the green synthesis of plastics
    Yungyeong Lee
    Cyrille Boyer
    Min Sang Kwon
    Nature Reviews Materials, 2022, 7 : 74 - 75
  • [44] Elemental iodine-catalyzed coupling of alkynylsilanes with acid chlorides:: A facile synthesis of α,β-acetylenic ketones
    Yadav, JS
    Reddy, BVS
    Reddy, MS
    SYNLETT, 2003, (11) : 1722 - 1724
  • [45] 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
  • [46] Visible-Light-Driven Synthesis of Arylstannanes from Arylazo Sulfones
    Lian, Chang
    Yue, Guanglu
    Mao, Jinshan
    Liu, Danyang
    Ding, Yi
    Liu, Zerong
    Qiu, Di
    Zhao, Xia
    Lu, Kui
    Fagnoni, Maurizio
    Protti, Stefano
    ORGANIC LETTERS, 2019, 21 (13) : 5187 - 5191
  • [47] 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
  • [48] Synthesis of Unsymmetrical Azoxyarenes via Copper-Catalyzed Aerobic Oxidative Dehydrogenative Coupling of Anilines with Nitrosoarenes
    Shi, Chongyang
    Xu, Boxia
    Fang, Xiaolan
    Yu, Xiaochun
    Jin, Huile
    Wang, Shun
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (07) : 1963 - 1967
  • [49] Iodine-Catalyzed Oxidative Coupling of Indolin-2-ones with Indoles: Synthesis of 3,3-Disubstituted Oxindole Compounds
    Li, Ruo-Pu
    Wang, Zheng-Lin
    Zhang, Yun-Hao
    Tan, Zhi-Yu
    Xu, Da-Zhen
    CHEMISTRYSELECT, 2022, 7 (28):
  • [50] Iodine-catalyzed tandem oxidative coupling reaction: A one-pot strategy for the synthesis of new coumarin-fused pyrroles
    Yahyavi, Hoda
    Heravi, Majid M.
    Mahdavi, Mohammad
    Foroumadi, Alireza
    TETRAHEDRON LETTERS, 2018, 59 (02) : 94 - 98