Photoredox-Catalyzed Transfer Aminochlorination of Unactivated Alkenes Using Oxime-Based Surrogates

被引:0
|
作者
Bicic, Sergiu [1 ]
Klare, Hendrik F. T. [1 ]
Oestreich, Martin [1 ]
机构
[1] Tech Univ Berlin, Inst Chem, D-10623 Berlin, Germany
来源
ACS CATALYSIS | 2025年
关键词
1,2-aminochlorination; oximes; photoredox catalysis; single electron transfer; transfer reactions; OLEFINS; ACCESS;
D O I
10.1021/acscatal.5c01290
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
An efficient photoredox-catalyzed strategy for simultaneous C(sp3)-N and C(sp3)-Cl bond formation using bench-stable and easy-to-handle oxime-based transfer reagents is reported. The distinct reactivity of these surrogates allows for a regioselective and redox-neutral 1,2-aminochlorination of unactivated alkenes by a radical-polar crossover pathway, initiated by single-electron reduction of the surrogate and its subsequent fragmentation. This method expands the utility of oxime-based surrogates in alkene difunctionalization, offering a versatile and scalable platform for the direct synthesis of aminochlorinated products with broad functional group compatibility under mild conditions.
引用
收藏
页码:6434 / 6438
页数:5
相关论文
共 49 条
  • [1] Photoredox-Catalyzed Hydrocarboxymethylation of Alkenes
    Fang, Jie
    Hu, Qiang
    Dong, Wan-Li
    Xu, Guo-Qiang
    Hu, Xiu-Qin
    Luo, Yong-Chun
    Xu, Peng-Fei
    CCS CHEMISTRY, 2021, 3 (10): : 95 - 104
  • [2] Recent Advances in Photoredox-Catalyzed Difunctionalization of Alkenes
    Liu, Yong
    Liu, Huan
    Liu, Xiao
    Chen, Zhangpei
    CATALYSTS, 2023, 13 (07)
  • [3] Photoredox-Catalyzed and Silane-Mediated Hydrofluoromethylation of Unactivated Alkenes with Fluoroiodomethane in Water
    Hu, Chen-Chen
    Tong, Chao-Lai
    Zhang, Yu-Yang
    Xu, Xiu-Hua
    Qing, Feng-Ling
    ORGANIC LETTERS, 2023, 25 (06) : 1035 - 1039
  • [4] Photoinduced Radical-Ionic Transfer of Various Chlorofluorocarbons to Alkenes from Oxime-Based Surrogates
    Zhang, Jinghui
    Zhang, Muliang
    Oestreich, Martin
    CCS CHEMISTRY, 2024, 6 (05): : 1222 - 1230
  • [5] Dual Nickel/Photoredox-Catalyzed Asymmetric Carbosulfonylation of Alkenes
    Du, Xiaoyong
    Cheng-Sanchez, Ivan
    Nevado, Cristina
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (23) : 12532 - 12540
  • [6] Visible-Light Photoredox-Catalyzed Acyl Lactonization of Alkenes with Acyl Chlorides
    Rao, Wei-Hao
    Li, Qi
    Li, Ying-Ge
    Jiang, Li-Li
    Yue, Ming-Xiao
    Zou, Guo-Dong
    Cao, Xinhua
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (18)
  • [7] Photoredox-Catalyzed Hydrodifluoroalkylation of Alkenes Using Difluorohaloalkyl Compounds and a Hantzsch Ester
    Sumino, Shuhei
    Uno, Misae
    Fukuyarna, Takahide
    Ryu, Ilhyong
    Matsuura, Makoto
    Yasnarnoto, Akinori
    Kishikawa, Yosuke
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (10) : 5469 - 5474
  • [8] Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams
    Giraldi, Valentina
    Magagnano, Giandomenico
    Giacomini, Daria
    Cozzi, Pier Giorgio
    Gualandi, Andrea
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2024, 20 : 2461 - 2468
  • [9] Photoredox-Catalyzed Selective Synthesis of Allylic Perfluoroalkanes from Alkenes
    Barthelemy, Anne-Laure
    Bourdreux, F.
    Dagousset, Guillaume
    Magnier, Emmanuel
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (45) : 10213 - 10216
  • [10] Photoredox-Catalyzed Synthesis of Homoallylamines from Unactivated Imines and Allyl Bromides
    Huang, Lan-Qian
    Yang, De-Yong
    Dong, Chun-Lin
    He, Yan-Hong
    Guan, Zhi
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (15) : 2553 - 2559