Selective Oxidative Cleavage of Benzyl C-N Bond under Metal-Free Electrochemical Conditions

被引:1
|
作者
Huang, Jiawei [1 ]
Li, Xiaoman [1 ]
Liu, Ping [1 ]
Wei, Yu [1 ]
Liu, Shuai [2 ]
Ma, Xiaowei [1 ]
机构
[1] Shihezi Univ, Sch Chem & Chem Engn, State Key Lab Incubat Base Green Proc Chem Engn, Shihezi 832003, Peoples R China
[2] Shihezi Univ, Bingtuan Energy Dev Inst, Shihezi 832003, Peoples R China
来源
MOLECULES | 2024年 / 29卷 / 12期
关键词
electrochemical oxidation; C-N bond cleavage; amine; aldehyde; ketone; CARBONYL-COMPOUNDS; AEROBIC OXIDATION; AMINES;
D O I
10.3390/molecules29122851
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
With the growing significance of green chemistry in organic synthesis, electrochemical oxidation has seen rapid development. Compounds undergo oxidation-reduction reactions through electron transfer at the electrode surface. This article proposes the use of electrochemical methods to achieve cleavage of the benzyl C-N bond. This method selectively oxidatively cleaves the C-N bond without the need for metal catalysts or external oxidants. Additionally, primary, secondary, and tertiary amines exhibit good adaptability under these conditions, utilizing water as the sole source of oxygen.
引用
收藏
页数:11
相关论文
共 50 条
  • [31] Transition Metal-Free N-S Bond Cleavage and C-N Bond Activation of Ugi-Adducts for Rapid Preparation of Primary Amides and α-Ketoamides
    Liu, Chao
    Van Der Eycken, Johan
    Van Der Eycken, Erik V.
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (53)
  • [32] Intermolecular Oxidative C-N Bond Formation under Metal-Free Conditions: Control of Chemoselectivity between Aryl sp2 and Benzylic sp3 C-H Bond Imidation
    Kim, Hyun Jin
    Kim, Jiyu
    Cho, Seung Hwan
    Chang, Sukbok
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (41) : 16382 - 16385
  • [33] Reusable ionic liquid-catalyzed oxidative coupling of azoles and benzylic compounds via sp3 C-N bond formation under metal-free conditions
    Liu, Wenbo
    Liu, Chenjiang
    Zhang, Yonghong
    Sun, Yadong
    Abdukadera, Ablimit
    Wang, Bin
    Li, He
    Ma, Xuecheng
    Zhang, Zengpeng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (26) : 7154 - 7158
  • [34] Organic Complexes Built by Halogenated Molecules: Unexpected in Situ C-N Bond Formation in Metal-Free Solvothermal Conditions
    Lue, Jian
    Han, Li-Wei
    Lin, Jing-Xiang
    Cao, Rong
    CRYSTAL GROWTH & DESIGN, 2011, 11 (06) : 2035 - 2038
  • [35] A facile access for the C-N bond formation by transition metal-free oxidative coupling of benzylic C-H bonds and amides
    Liu, Jie
    Zhang, Heng
    Yi, Hong
    Liu, Chao
    Lei, Aiwen
    SCIENCE CHINA-CHEMISTRY, 2015, 58 (08) : 1323 - 1328
  • [36] A facile access for the C-N bond formation by transition metal-free oxidative coupling of benzylic C-H bonds and amides
    Jie Liu
    Heng Zhang
    Hong Yi
    Chao Liu
    Aiwen Lei
    Science China Chemistry, 2015, 58 : 1323 - 1328
  • [37] Oxidative C-N Bond Cleavage of Cyclic Amines with Ammonium Hypochlorite
    Kaieda, Yuya
    Yamamoto, Kosuke
    Toguchi, Hiroyuki
    Hanazawa, Natsumi
    Kuriyama, Masami
    Onomura, Osamu
    SYNTHESIS-STUTTGART, 2024, 56 (10): : 1576 - 1584
  • [38] Metal-Free C-N or C-C Bond Cleavages of α-Azido Ketones: An Oxidative-Amidation Strategy for the Synthesis of α-Ketothioamides and Amides
    Yu, Pei
    Wang, Yuwei
    Zeng, Zhigang
    Chen, Yunfeng
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (22): : 14883 - 14891
  • [39] Transition-metal-free aerobic C-O bond formation via C-N bond cleavage
    Guo, Lirong
    Liu, Fengting
    Wang, Liying
    Yuan, Hairui
    Feng, Lei
    Lu, Haifeng
    Gao, Hongyin
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (09): : 1077 - 1081
  • [40] Metal-free synthesis of indolizines through oxidative C-C and C-N bond formations of C (sp3)-H bonds
    Reddy, N. Naresh Kumar
    Mohan, Darapaneni Chandra
    Adimurthy, Subbarayappa
    TETRAHEDRON LETTERS, 2016, 57 (10) : 1074 - 1078