Metal-free Photocatalytic Intermolecular anti-Markovnikov Hydroamination of Unactivated Alkenes

被引：13
|
作者：
Zhao, Gaoyuan [1 ,2 ]
Li, Juncheng [1 ]
Wang, Ting [1 ]
机构：
[1] SUNY Albany, Dept Chem, 1400 Washington Ave, Albany, NY 12222 USA
[2] SUNY Stony Brook, Dept Chem, 100 Nicolls Rd, Stony Brook, NY 11790 USA
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 18期
基金：
美国国家科学基金会;
关键词：
NITROGEN-RADICAL PRECURSORS; N-CENTERED RADICALS; SYNTHETIC APPLICATIONS; AMIDYL RADICALS; RAPID SYNTHESIS; LIGHT; PHOTOREDOX; ARENES; AMIDATION; PYRROLOINDOLINES;
D O I：
10.1002/ejoc.202100049
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The development of photocatalytic intermolecular hydroamination reaction between N-aminated dihydropyridines and unactivated alkenes is reported. Metal-free co-catalysts, rhodamine 6G and thiophenol, in presence of visible light are used to initiate the process. The transformation shows a broad substrate scope, both alkenes and amidyl radical can act as coupling partners. The radical strategy provides excellent anti-Markovnikov selectivity and regioselectivity in diene substrates.
引用
收藏
页码：2650 / 2654
页数：5
相关论文
共 50 条
  • [1] Photocatalytic intermolecular anti-Markovnikov hydroamination of unactivated alkenes with N-hydroxyphthalimide
    Ye, Zhi-Peng
    Hu, Yuan-Zhuo
    Xia, Peng-Ju
    Xiang, Hao-Yue
    Chen, Kai
    Yang, Hua
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (02): : 273 - 277
  • [2] Anti-Markovnikov Hydroamination of Unactivated Alkenes with Primary Alkyl Amines
    Miller, David C.
    Ganley, Jacob M.
    Musacchio, Andrew J.
    Sherwood, Trevor C.
    Ewing, William R.
    Knowles, Robert R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (42) : 16590 - 16594
  • [3] Intermolecular Anti-Markovnikov Hydroamination of Alkenes with Sulfonamides, Sulfamides, and Sulfamates
    Lin, Angela
    Karrasch, Mathis J.
    Yan, Qiaolin
    Ganley, Jacob M.
    Hejna, Benjamin G.
    Knowles, Robert R.
    [J]. ACS CATALYSIS, 2024, 14 (17): : 13098 - 13104
  • [4] Anti-Markovnikov Intermolecular Hydroamination of Alkenes and Alkynes: A Mechanistic View
    Escorihuela, Jorge
    Lledos, Agusti
    Ujaque, Gregori
    [J]. CHEMICAL REVIEWS, 2023, 123 (15) : 9139 - 9203
  • [5] Photocatalytic Anti-Markovnikov Hydroamination of Alkenes with Primary Heteroaryl Amines
    Geunes, Eric P.
    Meinhardt, Jonathan M.
    Wu, Emily J.
    Knowles, Robert R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (40) : 21738 - 21744
  • [6] Intermolecular Anti-Markovnikov Hydroamination of Unactivated Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer
    Zhu, Qilei
    Graff, David E.
    Knowles, Robert R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (02) : 741 - 747
  • [7] One-Pot Anti-Markovnikov Hydroamination of Unactivated Alkenes by Hydrozirconation and Amination
    Strom, Alexandra E.
    Hartwig, John F.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (17): : 8909 - 8914
  • [8] Photosensitized Anti-Markovnikov Hydroesterification of Unactivated Alkenes
    Sang, Tongzhi
    Zhou, Chenxing
    Li, Jun
    Liu, Xincong
    Yuan, Yong
    Bao, Xiazhen
    Zhao, Xiaolong
    Huo, Congde
    [J]. ORGANIC LETTERS, 2023, 25 (23) : 4371 - 4376
  • [9] Metal-free intermolecular aminochlorination of unactivated alkenes
    Zhu, Nengbo
    Li, Yajun
    Bao, Hongli
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (08): : 1303 - 1307
  • [10] Iodine（Ⅲ） reagent（ABX–N）-induced intermolecular anti-Markovnikov hydroazidation of unactivated alkenes
    Xiaonan Li
    Pinhong Chen
    Guosheng Liu
    [J]. Science China(Chemistry), 2019, (11) - 1541
12345