Synergy of Anodic Oxidation and Cathodic Reduction Leads to Electrochemical C-H Halogenation

被引:76
作者
Zhou, Zhilin [1 ]
Yuan, Yong [2 ]
Cao, Yangmin [1 ]
Qiao, Jin [1 ]
Yao, Anjin [1 ]
Zhao, Jing [1 ]
Zuo, Wanqing [1 ]
Chen, Wenjie [1 ]
Lei, Aiwen [1 ,2 ]
机构
[1] Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China
[2] Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies, Wuhan 430072, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
BOND FORMATION; METAL-FREE; ORGANIC ELECTROSYNTHESIS; FUNCTIONALIZATION; BROMINATION; CYCLIZATION; EFFICIENT; CATALYST; ALKENES; REAGENT;
D O I
10.1002/cjoc.201900091
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We herein uncovered an electrochemical C-H halogenation protocol that synergistically combines anodic oxidation and cathodic reduction for C-X bond formation. The reaction was demonstrated under exogenous-oxidant-free conditions. Moreover, this is the first example of activating CBr4, CHBr3, and CCl3Br under electrochemical conditions.
引用
收藏
页码:611 / 615
页数:5
相关论文
共 74 条
  • [1] Cooperative electrocatalytic alcohol oxidation with electron-proton-transfer mediators
    Badalyan, Artavazd
    Stahl, Shannon S.
    [J]. NATURE, 2016, 535 (7612) : 406 - 410
  • [2] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure
    Barder, TE
    Walker, SD
    Martinelli, JR
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) : 4685 - 4696
  • [3] KOtBu: A Privileged Reagent for Electron Transfer Reactions?
    Barham, Joshua P.
    Coulthard, Graeme
    Emery, Katie J.
    Doni, Eswararao
    Cumine, Florimond
    Nocera, Giuseppe
    John, Matthew P.
    Berlouis, Leonard E. A.
    McGuire, Thomas
    Tuttle, Tell
    Murphy, John A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (23) : 7402 - 7410
  • [4] Mechanistic considerations of halogenating enzymes
    Butler, Alison
    Sandy, Moriah
    [J]. NATURE, 2009, 460 (7257) : 848 - 854
  • [5] Tandem radical cyclization to construct poly-brominated 2-oxindoles
    Chen, Fengjuan
    Wang, Yajun
    Zhao, Shijun
    Jiang, Wei
    Huo, Congde
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (36) : 7710 - 7714
  • [6] An efficient and highly selective deprotecting method for β-(trimethylsilyl)ethoxymethyl ethers
    Chen, MY
    Lee, ASY
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) : 1384 - 1387
  • [7] Redox catalysis in organic electrosynthesis: basic principles and recent developments
    Francke, Robert
    Little, R. Daniel
    [J]. CHEMICAL SOCIETY REVIEWS, 2014, 43 (08) : 2492 - 2521
  • [8] Functionally Diverse Nucleophilic Trapping of Iminium Intermediates Generated Utilizing Visible Light
    Freeman, David B.
    Furst, Laura
    Condie, Allison G.
    Stephenson, Corey R. J.
    [J]. ORGANIC LETTERS, 2012, 14 (01) : 94 - 97
  • [9] Organic electrosynthesis: a promising green methodology in organic chemistry
    Frontana-Uribe, Bernardo A.
    Little, R. Daniel
    Ibanez, Jorge G.
    Palma, Agustin
    Vasquez-Medrano, Ruben
    [J]. GREEN CHEMISTRY, 2010, 12 (12) : 2099 - 2119
  • [10] Electrocatalytic Radical Dichlorination of Alkenes with Nucleophilic Chlorine Sources
    Fu, Niankai
    Sauer, Gregory S.
    Lin, Song
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (43) : 15548 - 15553