Visible-Light-Induced Insertion of Sulfur Dioxide Mediated by Electron Donor-Acceptor Complex: Synthesis and Photophysical Properties of 3-Sulfonyl Indolizines

被引:2
|
作者
Naud-Martin, Delphine [1 ,2 ]
Kosiuha, Marharyta [1 ,2 ]
Zucolotto Cocca, Leandro H. [3 ]
Retailleau, Pascal [4 ]
Mahuteau-Betzer, Florence [1 ,2 ]
De Boni, Leonardo [3 ]
Piguel, Sandrine [5 ]
机构
[1] Univ PSL, Inst Curie, CNRS, Inserm,U1196,UMR9187, F-91400 Orsay, France
[2] Univ Paris Saclay, CNRS, Inserm, UMR9187,U1196, F-91400 Orsay, France
[3] Univ Sao Paulo, Inst Fis Sao Carlos, CP 369, BR-13560970 Sao Carlos, SP, Brazil
[4] Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, cedex, F-91198 Gif Sur Yvette, France
[5] Univ Paris, Saclay Fac Pharm, CNRS, UMR 8076, F-91400 Orsay, France
关键词
electron donor-acceptor complex; indolizines; photocatalysis; sulfones; sulfur dioxide; DERIVATIVES; FLUOROPHORE; DRUGS; HOST;
D O I
10.1002/ejoc.202300125
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This work investigates a light-driven 3-component sulfonylation reaction of indolizines without needing any external photocatalyst. The mechanistic investigations support the formation of an electron donor-acceptor (EDA) complex in situ. This transformation offers a mild and sustainable approach with high functional group tolerance for the synthesis of 3-sulfonylated indolizines. This compound class has valuable photophysical properties and represents promising candidates in various applications related to fluorescence.
引用
收藏
页数:6
相关论文
共 38 条
  • [11] Visible-Light-Mediated (sp3)Cα-H Functionalization of Ethers Enabled by Electron Donor-Acceptor Complex
    Roy, Sourav
    Chatterjee, Indranil
    ACS ORGANIC & INORGANIC AU, 2022, 2 (04): : 306 - 311
  • [12] Visible-Light-Induced 3-Component Synthesis of Sulfonylated Oxindoles by Fixation of Sulfur Dioxide
    Liu, Nai-Wei
    Chen, Zhengkai
    Herbert, Andre
    Ren, Hongjun
    Manolikakes, Georg
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (41) : 5725 - 5734
  • [13] Visible-Light-Induced Decarboxylative Cyclization/Hydrogenation Cascade Reaction to Access Phenanthridin-6-yl(aryl)methanol by an Electron Donor-Acceptor Complex
    Shi, Wei
    Ma, Fang
    Li, Pinhua
    Wang, Lei
    Miao, Tao
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (21): : 13808 - 13817
  • [14] Visible-Light-Driven Synthesis of Aryl Xanthates and Aryl Dithiocarbamates via an Electron Donor-Acceptor Complex
    Zhang, Mingjun
    Wang, Beibei
    Cao, Yunpeng
    Liu, Yuxiu
    Wang, Ziwen
    Wang, Qingmin
    ORGANIC LETTERS, 2022, 24 (48) : 8895 - 8900
  • [15] Synthesis and Photophysical Properties of a Sc3N@C80-Corrole Electron Donor-Acceptor Conjugate
    Liu, Bin
    Fang, Hongyun
    Li, Xiaofang
    Cai, Wenting
    Bao, Lipiao
    Rudolf, Marc
    Plass, Fabian
    Fan, Louzhen
    Lu, Xing
    Guldi, Dirk M.
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (02) : 746 - 752
  • [16] Visible-Light-Mediated Synthesis of Anomeric S-Aryl Glycosides via Electron Donor-Acceptor Complex Using Thianthrenium Salts
    Zhou, Zhuoyi
    Zhang, Yufeng
    Yu, Zhiqiang
    Liu, Yuping
    Wang, Zhen
    Zhang, Qingju
    Wang, Liming
    MOLECULES, 2025, 30 (06):
  • [17] Electron donor-acceptor (EDA) complex mediated visible-light driven sulfur-fluorine bond reduction of pentafluorosulfanyl arenes using potassium iodide
    Uchikura, Tatsuhiro
    Akutsu, Fua
    Akiyama, Takahiko
    CHEMICAL COMMUNICATIONS, 2025,
  • [18] Visible-Light-Induced Synthesis of Alkylsulfonated Isoquinolinones from 2-Aryl Indoles/Benzimidazoles through Insertion of Sulfur Dioxide
    Liu, Xin-Qian
    Guo, Yang
    Yu, Wen-Qin
    Xiong, Biquan
    Huang, Peng-Fei
    Tang, Ke-Wen
    Liu, Yu
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13): : 9293 - 9305
  • [19] Visible-Light Driven, Metal-Free Hydroalkylation of Alkenes Mediated by Electron Donor-Acceptor Complex Using Benzothiazolines
    Uchikura, Tatsuhiro
    Fujii, Tatsuya
    Moriyama, Kaworuko
    Akiyama, Takahiko
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2021, 94 (12) : 2962 - 2966
  • [20] Visible-Light-Promoted C3-Sulfenylindoles with Arylsulfonyl Chlorides via Electron Donor-Acceptor Complex
    Xue, Ziqian
    Yang, Wenjing
    Huang, Qiuzhan
    Zhou, Cong-Ying
    Guo, Zhen
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (11): : 7591 - 7597