Chemoselective Electro-oxidation of Allyl Arene to Ester

被引:0
|
作者
Li Mengfan [1 ]
Cheng Xu [1 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, Nanjing 210023, Peoples R China
基金
中国国家自然科学基金;
关键词
allyl; benzyl; electrochemistry; esterification; ACTIVATION; OXIDATION; ALCOHOLS;
D O I
10.6023/cjoc202309019
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An electrochemical C-H and C-C bond esterification reaction with allyl arene as a substrate is reported. This oxidation takes place selectively at the benzyl(+) allyl C-H site instead of other benzylic C-H groups. Since the reaction does not require acid/base catalysis for esterification, tertiary alcohol is suitable for the synthesis of the corresponding ester. In addition, side reactions such as transesterification can be avoided with this neutral protocol.
引用
收藏
页码:1005 / 1012
页数:8
相关论文
共 25 条
  • [1] Electrochemical Benzylic C(sp3)-H Acyloxylation
    Atkins, Alexander P.
    Rowett, Albert C.
    Heard, David M.
    Tate, Joseph A.
    Lennox, Alastair J. J.
    [J]. ORGANIC LETTERS, 2022, : 5105 - 5108
  • [2] Electrochemical halogenation/semi-pinacol rearrangement of allylic alcohols using inorganic halide salt: an eco-friendly route to the synthesis of β-halocarbonyls
    Chen, Chao
    Kang, Jun-Chen
    Mao, Chen
    Dong, Jia-Wei
    Xie, Yu-Yang
    Ding, Tong-Mei
    Tu, Yong-Qiang
    Chen, Zhi-Min
    Zhang, Shu-Yu
    [J]. GREEN CHEMISTRY, 2019, 21 (15) : 4014 - 4019
  • [3] Continuous Flow Electrochemistry Enables Practical and Site-Selective C-H Oxidation
    Chen, Tian-Sheng
    Long, Hao
    Gao, Yuxing
    Xu, Hai-Chao
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (40)
  • [4] Recent Applications of Homogeneous Catalysis in Electrochemical Organic Synthesis
    Cheng, Xu
    Lei, Aiwen
    Mei, Tian-Sheng
    Xu, Hai-Chao
    Xu, Kun
    Zeng, Chengchu
    [J]. CCS CHEMISTRY, 2022, 4 (04): : 1120 - 1152
  • [5] C-H Activation: Toward Sustainability and Applications
    Dalton, Toryn
    Faber, Teresa
    Glorius, Frank
    [J]. ACS CENTRAL SCIENCE, 2021, 7 (02) : 245 - 261
  • [6] β-Functionalized and α,β-Difunctionalized Ketones from 1-Arylallylic Alcohols via Dipotassio α,β-Dianion Intermediates
    Hayashi, Rikuo
    Ando, Kaori
    Udagawa, Taro
    Sai, Masahiro
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (06) : 826 - 833
  • [7] Electrochemical PINOylation of Methylarenes: Improving the Scope and Utility of Benzylic Oxidation through Mediated Electrolysis
    Hoque, Md Asmaul
    Twilton, Jack
    Zhu, Jieru
    Graaf, Matthew D.
    Harper, Kaid C.
    Tuca, Emilian
    DiLabio, Gino A.
    Stahl, Shannon S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (33) : 15295 - 15302
  • [8] Scalable and sustainable electrochemical allylic C-H oxidation
    Horn, Evan J.
    Rosen, Brandon R.
    Chen, Yong
    Tang, Jiaze
    Chen, Ke
    Eastgate, Martin D.
    Baran, Phil S.
    [J]. NATURE, 2016, 533 (7601) : 77 - 81
  • [9] Electrochemical Semipinacol Rearrangements of Allylic Alcohols: Construction of All-Carbon Quaternary Stereocenters
    Kang, Jun-Chen
    Tu, Yong-Qiang
    Dong, Jia-Wei
    Chen, Chao
    Zhou, Jia
    Ding, Tong-Mei
    Zai, Jian-Tao
    Chen, Zhi-Min
    Zhang, Shu-Yu
    [J]. ORGANIC LETTERS, 2019, 21 (08) : 2536 - 2540
  • [10] Recent advances in oxidative allylic C-H functionalization via group IX-metal catalysis
    Kazerouni, Amaan M.
    McKoy, Quincy A.
    Blakey, Simon B.
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (87) : 13287 - 13300