Insertion of sulfur dioxide via a radical process: an efficient route to sulfonyl compounds

被引:311
|
作者
Qiu, Guanyinsheng [1 ]
Zhou, Kaida [2 ]
Gao, Liang [3 ]
Wu, Jie [2 ]
机构
[1] Jiaxing Univ, Coll Biol Chem Sci & Engn, 118 Jiahang Rd, Jiaxing 314001, Peoples R China
[2] Fudan Univ, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China
[3] Ganzhou Teachers Coll, Dept Nat Sci & Comp Sci, Ganzhou 341000, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 04期
基金
中国国家自然科学基金;
关键词
PALLADIUM-CATALYZED AMINOSULFONYLATION; C-H FUNCTIONALIZATION; BETA-KETO SULFONES; 3-COMPONENT REACTION; ONE-POT; VICINAL DIFUNCTIONALIZATION; MULTICOMPONENT REACTION; C(SP(3))-H BOND; SULPHUR DIOXIDE; RECENT PROGRESS;
D O I
10.1039/c7qo01073g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This review is focused on the recent advances in the chemistry of sulfur dioxide fixation through a radical process. Diverse sulfonyl compounds can be obtained efficiently under mild conditions. In general, aryl radicals, vinyl radicals, alkyl radicals, and nitrogen-centered radicals can react with sulfur dioxide, giving rise to sulfonyl radical intermediates. The resulting sulfonyl radicals can be captured by nucleophiles, olefins, and alkynes. The sources of aryl radicals from aryldiazonium salts, aryl halides, and diaryliodonium salts are demonstrated. It is believed that more amazing SO2-based achievements will be developed in the near future.
引用
收藏
页码:691 / 705
页数:15
相关论文
共 50 条
  • [1] Generation of benzosultams via a radical process with the insertion of sulfur dioxide
    Zhou, Kaida
    Xia, Hongguang
    Wu, Jie
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (06): : 1121 - 1124
  • [2] Generation of (E)-β-sulfonyl enamines from sulfur dioxide via a radical process
    Tu, Xiaodong
    Huang, Jiapian
    Xie, Wenlin
    Zhu, Tonghao
    Wu, Jie
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (08) : 1789 - 1794
  • [3] Recent progress in sulfonyl fluoride synthesis via the radical sulfur dioxide insertion and fluorination strategy
    Zhang, Haozhen
    Xiao, Wangchuan
    Wu, Fanhong
    Ma, Xiaoyu
    Liu, Chao
    SCIENCE CHINA-CHEMISTRY, 2024,
  • [4] Access to chiral β-sulfonyl carbonyl compounds via photoinduced organocatalytic asymmetric radical sulfonylation with sulfur dioxide
    He, Fu-Sheng
    Zhang, Chun
    Jiang, Minghui
    Lou, Lujun
    Wu, Jie
    Ye, Shengqing
    CHEMICAL SCIENCE, 2022, 13 (30) : 8834 - 8839
  • [5] SULFUR-DIOXIDE INSERTION INTO ORGANOCOBALOXIMES - A TRUE INSERTION OR A CASE OF RADICAL CHAIN PROCESS
    GUPTA, BD
    ROY, M
    OBEROI, M
    DIXIT, V
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 430 (02) : 197 - 204
  • [6] SULFUR-DIOXIDE INSERTION INTO ORGANOCOBALOXIMES - A TRUE INSERTION OR A CASE OF RADICAL CHAIN PROCESS
    GUPTA, BD
    ROY, S
    ROY, M
    TETRAHEDRON LETTERS, 1987, 28 (11) : 1219 - 1222
  • [7] A copper-catalyzed insertion of sulfur dioxide via radical coupling
    Zhang, Jun
    Yang, Min
    Liu, Jin-Biao
    He, Fu-Sheng
    Wu, Jie
    CHEMICAL COMMUNICATIONS, 2020, 56 (21) : 3225 - 3228
  • [8] A general route to sulfones via insertion of sulfur dioxide promoted by cobalt oxide
    Zheng, Danqing
    Chen, Mo
    Yao, Liangqing
    Wu, Jie
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (08): : 985 - 988
  • [9] Photoinduced efficient synthesis of cyanoalkylsulfonylated oxindoles via sulfur dioxide insertion
    Teng, Fan
    Du, Juan
    Xun, Changping
    Zhu, Mengxue
    Lu, Ziqin
    Jiang, Hongmei
    Chen, Yuling
    Li, Yu
    Gui, Qing-Wen
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (41) : 8929 - 8933
  • [10] Recent advances in the sulfonylation of alkenes with the insertion of sulfur dioxide via radical reactions
    Qiu, Guanyinsheng
    Lai, Lifang
    Cheng, Jiang
    Wu, Jie
    CHEMICAL COMMUNICATIONS, 2018, 54 (74) : 10405 - 10414