A radical Smiles rearrangement difunctionalization of activated alkenes via desulfonylation and insertion of sulfur dioxide relay strategy

被引:7
|
作者
Tian, Si-Wei [1 ]
Luo, Zhen-Tao [1 ]
Xiong, Bi-Quan [1 ]
Tang, Ke-Wen [1 ]
Huang, Peng-Fei [1 ]
Liu, Yu [1 ]
机构
[1] Hunan Inst Sci & Technol, Dept Chem & Chem Engn, Yueyang 414006, Hunan, Peoples R China
基金
中国国家自然科学基金;
关键词
4-SUBSTITUTED HANTZSCH ESTERS; ALKYLATION; MIGRATION/DESULFONYLATION; SULFONYLATION; CONSTRUCTION; SULFONES;
D O I
10.1039/d4gc00186a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A visible-light-induced difunctionalization of activated alkenes for building alkylsulfonylated oxindoles and amides through a radical Smiles rearrangement strategy was reported. A tandem SO2 insertion/1,4-aryl migration/desulfonylation/cyclization sequence was involved in this transformation. Readily available Hantzsch esters served as alkylation reagents. Two different products were constructed depending on the substituent group of the nitrogen atom.
引用
收藏
页码:6774 / 6778
页数:5
相关论文
共 23 条
  • [1] Vicinal Difunctionalization of Alkenes through a Multicomponent Reaction with the Insertion of Sulfur Dioxide
    Zhang, Jun
    An, Yuanyuan
    Wu, Jie
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (40) : 9477 - 9480
  • [2] Accessing chiral sulfones bearing quaternary carbon stereocenters via photoinduced radical sulfur dioxide insertion and Truce–Smiles rearrangement
    Jiapian Huang
    Fei Liu
    Ling-Hui Zeng
    Shaoyu Li
    Zhiyuan Chen
    Jie Wu
    Nature Communications, 13
  • [3] 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
  • [4] Accessing chiral sulfones bearing quaternary carbon stereocenters via photoinduced radical sulfur dioxide insertion and Truce-Smiles rearrangement
    Huang, Jiapian
    Liu, Fei
    Zeng, Ling-Hui
    Li, Shaoyu
    Chen, Zhiyuan
    Wu, Jie
    NATURE COMMUNICATIONS, 2022, 13 (01)
  • [5] 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,
  • [6] Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/Smiles rearrangement cascade
    He, Chonglong
    Wang, Yulong
    Li, Quan-Xin
    Yan, Zichen
    Zhang, Keyuan
    Ni, Shao-Fei
    Duan, Xin-Hua
    Liu, Le
    CHINESE CHEMICAL LETTERS, 2025, 36 (05)
  • [7] 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
  • [8] BENZIDINE REARRANGEMENT VIA A CATION RADICAL IN LIQUID SULFUR-DIOXIDE
    NOJIMA, M
    ANDO, T
    TOKURA, N
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (14): : 1504 - 1507
  • [9] Radical relay strategy for the construction of alkylsulfonated indolo[2,1-a]isoquinoline-6(5H)-ones via SO2 insertion/Smiles rearrangement
    Tian, Si-Wei
    Zhong, Long-Jin
    Fan, Jian-Hong
    Tang, Ke-Wen
    Liu, Yu
    CHEMICAL COMMUNICATIONS, 2024, 60 (81) : 11568 - 11571
  • [10] 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