Visible-light-driven intramolecular xanthylation of remote unactivated C(sp3)-H bonds

被引:19
|
作者
Chen, Hang [2 ]
Zhou, Yang [2 ]
Lei, Panpan [2 ]
Wang, Haifeng [1 ]
Yan, Qiongjiao [1 ]
Properzi, Roberta [5 ]
Wang, Wei [1 ]
Jing, Linhai [1 ,2 ]
Chen, Fener [1 ,3 ,4 ]
机构
[1] Wuhan Inst Technol, Pharmaceut Res Inst, Wuhan 430205, Peoples R China
[2] China West Normal Univ, Chem Synth & Pollut Control Key Lab Sichuan Prov, Nanchong 637009, Peoples R China
[3] Fudan Univ, Engn Ctr Catalysis & Synth Chiral Mol, Dept Chem, Shanghai 200433, Peoples R China
[4] Shanghai Engn Ctr Ind Catalysis Chiral Drugs, Shanghai 200433, Peoples R China
[5] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
来源
GREEN SYNTHESIS AND CATALYSIS | 2023年 / 4卷 / 04期
基金
中国国家自然科学基金;
关键词
C -H functionalization; 5 -Hydrogen atom transfer; Photocatalytic; Site -speci fic; Xanthylation; RADICAL REACTIONS; FUNCTIONALIZATIONS; CHEMISTRY; SKELETON; ROUTE;
D O I
10.1016/j.gresc.2022.07.003
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Visible light-mediated site-specific C(sp3)-H xanthylation of amides has been accomplished using N-xanthylamides. The N-centered radicals generated by light initiation of N-xanthylamide substrates undergo 1,5-hydrogen atom transfer to form benzylic or alkyl radical intermediates under metal-and catalyst-free conditions. This method exhibits a broad substrate scope, high functional group tolerance, and high regioselectivity. Furthermore, this strategy provides straightforward access to a range of derivatives through the subsequent elaboration of the xanthate group.
引用
收藏
页码:350 / 354
页数:5
相关论文
共 50 条
  • [31] Mechanism and Origins of Enantioselectivity of Iridium-Catalyzed Intramolecular Silylation of Unactivated C(sp3)-H Bonds
    Zhang, Mei
    Liang, Jiaqi
    Huang, Genping
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (04): : 2372 - 2376
  • [32] Controllable Intramolecular Unactivated C(sp3)-H Amination and Oxygenation of Carbamates
    Guo, Qihang
    Ren, Xiang
    Lu, Zhan
    ORGANIC LETTERS, 2019, 21 (04) : 880 - 884
  • [33] Benzylic C(sp3)-H Alkoxylation through Visible-Light-Driven Oxidative Radical-Polar Crossover
    Yamashita, Kenji
    Kawahara, Fumiya
    Hamashima, Yoshitaka
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (04)
  • [34] Rhodium(III)-Catalyzed Amidation of Unactivated C(sp3)H Bonds
    Wang, He
    Tang, Guodong
    Li, Xingwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (44) : 13049 - 13052
  • [35] Photoinduced Activation of Unactivated C(sp3)-H Bonds and Acylation Reactions
    Ren, Chen-Chao
    Wang, Tian-Qi
    Zhang, Yu
    Peng, Dao
    Liu, Xiao-Qing
    Wu, Qing-An
    Liu, Xue-Fen
    Luo, Shu-Ping
    CHEMISTRYSELECT, 2021, 6 (10): : 2523 - 2528
  • [36] Visible-Light-Driven Organophotocatalyzed Multicomponent Approach for Tandem C(sp3)-H Activation and Alkylation Followed by Trifluoromethylthiolation
    Ghosh, Krishna Gopal
    Das, Debabrata
    Garai, Sumit
    Chandu, Palasetty
    Sureshkumar, Devarajulu
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (13): : 8611 - 8622
  • [37] Organocatalytic Enantioselective Functionalization of Unactivated Indole C(sp3)-H Bonds
    Ma, Dengke
    Zhang, Zhihan
    Chen, Min
    Lin, Zhenyang
    Sun, Jianwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (44) : 15916 - 15921
  • [38] Visible-Light-Driven Palladium-Catalyzed Radical Alkylation of C-H Bonds with Unactivated Alkyl Bromides
    Zhou, Wen-Jun
    Cao, Guang-Mei
    Shen, Guo
    Zhu, Xing-Yong
    Gui, Yong-Yuan
    Ye, Jian-Heng
    Sun, Liang
    Liao, Li-Li
    Li, Jing
    Yu, Da-Gang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (49) : 15683 - 15687
  • [39] Visible-Light-Promoted Remote C(sp3)-H Amidation and Chlorination
    Qin, Qixue
    Yu, Shouyun
    ORGANIC LETTERS, 2015, 17 (08) : 1894 - 1897
  • [40] Visible Light-Induced Unactivated δ-C(sp3)-H Amination of Alcohols Catalyzed by Iron
    Jue, Zhaofan
    Huang, Yahao
    Qian, Jiahui
    Hu, Peng
    CHEMSUSCHEM, 2022, 15 (20)