Radical Hydro-Fluorosulfonylation of Propargylic Alcohols via Electron Donor-Acceptor Photoactivation

被引:9
|
作者
Zhang, Yingyin [1 ]
Feng, Qingyuan [1 ]
Zheng, Yu [1 ]
Lu, Yanju [1 ]
Liao, Saihu [2 ]
Huang, Shenlin [1 ,3 ]
机构
[1] Nanjing Forestry Univ, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat F, Int Innovat Ctr Forest Chem & Mat, Nanjing 210037, Jiangsu, Peoples R China
[2] Xiamen Univ, State Key Lab Phys Chem Solid Surfaces, Xiamen 361005, Fujian, Peoples R China
[3] Hunan Normal Univ, Coll Chem & Chem Engn, Key Lab Chem Biol & Tradit Chinese Med Res, Minist Educ China, Changsha 410081, Hunan, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1021/acs.orglett.4c00010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A radical hydro-fluorosulfonylation of propargyl alcohols with FSO2Cl is presented based on the photoactivation of the electron donor-acceptor (EDA) complex. The reaction avoids the requirement for photocatalysts, bases, hydrogen donor reagents, any other additives, and harsh conditions, enabling the facile synthesis of various functionalized gamma-hydroxy (E)-alkenylsulfonyl fluorides. These multifunctional sulfonyl fluorides can be further diversified, providing access to various privileged molecules of biological relevance.
引用
收藏
页码:1410 / 1415
页数:6
相关论文
共 50 条
  • [1] Radical Ring-Opening Fluorosulfonylation of Methylenecyclobutanols via Electron Donor-Acceptor Photoactivation
    He, Tianyu
    Liang, Chaoqiang
    Jiang, Ping
    Liang, Hui
    Liao, Saihu
    Huang, Shenlin
    ORGANIC LETTERS, 2024, 26 (26) : 5577 - 5581
  • [2] Radical Hydro-Fluorosulfonylation of Unactivated Alkenes and Alkynes
    Wang, Peng
    Zhang, Honghai
    Zhao, Mingqi
    Ji, Shuangshuang
    Lin, Lu
    Yang, Na
    Nie, Xingliang
    Song, Jinshuai
    Liao, Saihu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (39)
  • [3] Fluorosulfonyl Arylation of Alkynes via Electron Donor-Acceptor Photoactivation
    Cheng, Haoyuan
    He, Tianyu
    Chen, Dengfeng
    Zheng, Yu
    Lu, Yanju
    Liang, Hui
    Liao, Saihu
    Huang, Shenlin
    ORGANIC LETTERS, 2024, 26 (17) : 3581 - 3585
  • [4] Recent Advances in Borylation via Electron Donor-Acceptor Complex Photoactivation
    Hu, Guanwen
    Wang, Zhiyong
    Wang, Xinmou
    Quan, Yangjian
    CHEMPHOTOCHEM, 2023, 7 (11)
  • [5] A general electron donor-acceptor complex for photoactivation of arenes via thianthrenation
    Sun, Kai
    Shi, Anzai
    Liu, Yan
    Chen, Xiaolan
    Xiang, Panjie
    Wang, Xiaotong
    Qu, Lingbo
    Yu, Bing
    CHEMICAL SCIENCE, 2022, 13 (19) : 5659 - 5666
  • [6] Switchable carbo-fluorosulfonylation and hydro-fluorosulfonylation of alkenes enabled by bifunctional fluorosulfonyl radical precursors
    Xiong, Ting
    Chen, Qi-Long
    Chen, Zhi-Da
    Yi, Ji-Tao
    Wang, Sheng-Cai
    Lu, Gui
    Chan, Albert S. C.
    Weng, Jiang
    CHEM CATALYSIS, 2023, 3 (12):
  • [7] Sustainable Thioetherification via Electron Donor-Acceptor Photoactivation Using Thianthrenium Salts
    Cabrera-Afonso, Maria Jesus
    Granados, Albert
    Molander, Gary A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (22)
  • [8] Thianthrenium-enabled sulfonylation via electron donor-acceptor complex photoactivation
    Granados, Albert
    Cabrera-Afonso, Maria Jesus
    Escolano, Marcos
    Badir, Shorouk O.
    Molander, Gary A.
    CHEM CATALYSIS, 2022, 2 (04): : 898 - 907
  • [9] C-H Functionalization of Heteroarenes via Electron Donor-Acceptor Complex Photoactivation
    Mondal, Madhusudan
    Ghosh, Sumit
    Lai, Dipti
    Hajra, Alakananda
    CHEMSUSCHEM, 2024,
  • [10] A General Organocatalytic System for Electron Donor-Acceptor Complex Photoactivation and Its Use in Radical Processes
    de Pedro Beato, Eduardo
    Spinnato, Davide
    Zhou, Wei
    Melchiorre, Paolo
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (31) : 12304 - 12314