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.
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页数:11
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  • [21] Electrochemical Oxidative Dehydrogenative Coupling of Sulfoximines to Construct N-sulfenyl and N-phosphinyl Sulfoximines
    Li, Xiaoman
    Huang, Jiawei
    Xu, Liang
    Liu, Jichang
    Wei, Yu
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (24) : 4647 - 4653
  • [22] Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls
    Li, Xue
    Bai, Fang
    Liu, Chaogan
    Ma, Xiaowei
    Gu, Chengzhi
    Dai, Bin
    [J]. ORGANIC LETTERS, 2021, 23 (19) : 7445 - 7449
  • [23] Recent advances in electrochemical C-H bond amination
    Liu, Chen
    Liu, Jixuan
    Li, Wenyi
    Lu, Huan
    Zhang, Yunfei
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (20) : 5309 - 5330
  • [24] Metal- and oxidant-free electrochemically promoted oxidative coupling of amines
    Liu, Gang
    Liu, Sen
    Li, Zhen
    Chen, Hengyu
    Li, Jiashuai
    Zhang, Yalin
    Shen, Guodong
    Yang, Bingchuan
    Hu, Xiude
    Huang, Xianqiang
    [J]. RSC ADVANCES, 2021, 12 (01) : 118 - 122
  • [25] Electrochemical utilization of methanol and methanol-d4 as a C1 source to access (deuterated) 2,3-dihydroquinazolin-4(1H)-one
    Liu, Mingzhu
    Xu, Liang
    Wei, Yu
    [J]. CHINESE CHEMICAL LETTERS, 2022, 33 (03) : 1559 - 1562
  • [26] Hydrogenated Cu2O\Au@CeO2 Z-scheme catalyst for photocatalytic oxidation of amines to imines
    Liu, Yingying
    Chen, Yajie
    Zhou, Wei
    Jiang, Baojiang
    Zhang, Xin
    Tian, Guohui
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2018, 8 (21) : 5535 - 5543
  • [27] Molecular iodine mediated oxidative cleavage of the C-N bond of aryl and heteroaryl (dimethylamino)methyl groups into aldehydes
    Mandrekar, Ketan S.
    Tilve, Santosh G.
    [J]. NEW JOURNAL OF CHEMISTRY, 2021, 45 (09) : 4152 - 4155
  • [28] Direct Electrosynthesis of Ketones from Benzylic Methylenes by Electrooxidative C-H Activation
    Meng, Li
    Su, Jihu
    Zha, Zhenggen
    Zhang, Li
    Zhang, Zhenlei
    Wang, Zhiyong
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (18) : 5542 - 5545
  • [29] Cycloaddition of carbonyl compounds and alkynes to (di) silenes and (di) germenes: reactivity and mechanism
    Milnes, Kaarina K.
    Pavelka, Laura C.
    Baines, Kim M.
    [J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (04) : 1019 - 1035
  • [30] Size-Dependent Catalytic Activity of Palladium Nanoparticles Fabricated in Porous Organic Polymers for Alkene Hydrogenation at Room Temperature
    Mondal, John
    Quang Thang Trinh
    Jana, Avijit
    Ng, Wilson Kwok Hung
    Borah, Parijat
    Hirao, Hajime
    Zhao, Yanli
    [J]. ACS APPLIED MATERIALS & INTERFACES, 2016, 8 (24) : 15307 - 15319