Visible Light/Tertiary Amine Promoted Synergistic Hydroxydifluoroacetamidation of Unactivated Alkenes under Air

被引:26
|
作者
Sun, Bin [1 ]
Zhu, Rui [2 ]
Zhuang, Xiaohui [1 ]
Shi, Xiayue [2 ]
Huang, Panyi [2 ]
Yan, Zhiyang [1 ]
Yu, Chuanming [2 ]
Jin, Can [1 ,2 ]
机构
[1] Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg Gr, Hangzhou 310014, Peoples R China
[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Peoples R China
基金
中国国家自然科学基金;
关键词
RADICAL-ADDITION; LIGHT PHOTOREDOX; DIFLUOROALKYLATION; FLUORINE; DIFLUOROMETHYLATION; CATALYSIS; OLEFINS;
D O I
10.1021/acs.orglett.0c04216
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and novel method for regioselective hydroxydifluoroacetamidation of alkenes with bromodifluor-oacetamides has been achieved via a tandem radical pathway mediated by photoredox catalysis under metal-free conditions. This transformation proceeded smoothly in the presence of Rhodamine 6G, affording a series of alpha,alpha-difluoro-gamma-hydroxyacetamides in moderate to excellent yields. The significant advantages of this protocol are the low-cost photocatalyst, readily available starting materials, synthetic convenience, and wide functional group compatibility.
引用
收藏
页码:617 / 622
页数:6
相关论文
共 50 条
  • [1] Visible light-promoted oxycarbonylation of unactivated alkenes
    Yang, Hefei
    Wang, Yuanrui
    Wang, Le-Cheng
    Wu, Xiao-Feng
    EES CATALYSIS, 2024, 2 (06): : 1247 - 1252
  • [2] Visible-light-promoted phosphorylation carbonylation of unactivated alkenes
    Miao, Ren-Guan
    Wang, Yuanrui
    Wu, Xiao-Feng
    JOURNAL OF CATALYSIS, 2025, 442
  • [3] Catalyst-Free and Visible Light Promoted Aminofluoroalkylation of Unactivated Alkenes: An Access to Fluorinated Aziridines
    Liu Xiao-Xiao
    Jia Jia
    Wang Ze
    Zhang Yu-Ting
    Chen Jiao
    Yang Ke
    He Chun-Yang
    Zhao Liang
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (13) : 2604 - 2608
  • [4] Visible-Light-Promoted Carboimination of Unactivated Alkenes for the Synthesis of Densely Functionalized Pyrroline Derivatives
    Cai, Sai-Hu
    Xie, Jia-Hao
    Song, Shengjin
    Ye, Lu
    Feng, Chao
    Loh, Teck-Peng
    ACS CATALYSIS, 2016, 6 (08): : 5571 - 5574
  • [5] Hydrosulfonylation of Unactivated Alkenes by Visible Light Photoredox Catalysis
    Wang, Juan-Juan
    Yu, Wei
    ORGANIC LETTERS, 2019, 21 (22) : 9236 - 9240
  • [6] Visible-Light-Induced Iminothiolation of Unactivated Alkenes
    Wang, Ding-Xing
    Cai, Sai-Hu
    Liu, Haidong
    Ye, Lu
    Zhu, Chuan
    Feng, Chao
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (06) : 1386 - 1389
  • [7] Hydrophosphinylation of unactivated alkenes with secondary phosphine oxides under visible-light photocatalysis
    Yoo, Woo-Jin
    Kobayashi, Shu
    GREEN CHEMISTRY, 2013, 15 (07) : 1844 - 1848
  • [8] Visible Light-Promoted Isomerization of Alkenes
    Zhang, Hao
    Yu, Shouyun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (01) : 95 - 108
  • [9] Visible-Light-Promoted Selenofunctionalization of Alkenes
    Conner, Elizabeth S.
    Crocker, Katherine E.
    Fernando, Ranelka G.
    Fronczek, Frank R.
    Stanley, George G.
    Ragains, Justin R.
    ORGANIC LETTERS, 2013, 15 (21) : 5558 - 5561
  • [10] Visible light promoted sulfonylation and sulfonylcarbonylation of alkenes
    Min, Wenjian
    Guo, Guozhe
    Yang, Caixia
    Huo, Congde
    TETRAHEDRON LETTERS, 2020, 61 (25)