Copper catalyzed oxidative deamination of Betti bases: an efficient approach for benzoylation/formylation of naphthols and phenols

被引：35
作者：
Deb, Mohit L. [1 ]
Pegu, Choitanya Dev [1 ]
Borpatra, Paran J. [1 ]
Baruah, Pranjal K. [1 ]
机构：
[1] Gauhati Univ, Dept Appl Sci, GUIST, Gauhati 781014, Assam, India
来源：
RSC ADVANCES | 2016年 / 6卷 / 46期
关键词：
C-H BOND; DEHYDROGENATIVE COUPLING REACTIONS; SURFACTANT-COMBINED CATALYST; MANNICH-TYPE REACTIONS; FRIES REARRANGEMENT; TERTIARY-AMINES; ENANTIOSELECTIVE ADDITION; BENZOPHENONE DERIVATIVES; MULTICOMPONENT SYNTHESIS; FACILE SYNTHESIS;
D O I：
10.1039/c6ra04567g
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient route for benzoylation or formylation of naphthols/phenols is developed via oxidative deamination of Betti bases. A copper salt catalyst with TBHP as an oxidant is used. Water is used as a reagent as well as solvent. The reaction proceeds through a regioselective radical pathway. Most importantly, the position of acylation is unambiguous. The method is also applicable to non-hydroxy substrates.
引用
收藏
页码：40552 / 40559
页数：8
相关论文
共 152 条
  • [1] Oxidative deamination of benzylamine by glycoxidation
    Akagawa, M
    Sasaki, T
    Suyama, K
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (07) : 1411 - 1417
  • [2] Oxidative deamination by hydrogen peroxide in the presence of metals
    Akagawa, M
    Suyama, K
    [J]. FREE RADICAL RESEARCH, 2002, 36 (01) : 13 - 21
  • [3] C-H functionalization of tertiary amines by cross dehydrogenative coupling reactions: solvent-free synthesis of α-aminonitriles and β-nitroamines under aerobic condition
    Alagiri, Kaliyamoorthy
    Prabhu, Kandikere Ramaiah
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (04) : 835 - 842
  • [4] Green Chemistry: Principles and Practice
    Anastas, Paul
    Eghbali, Nicolas
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) : 301 - 312
  • [5] [Anonymous], 2012, ANGEW CHEM
  • [6] Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
  • [7] A general and convenient route to oxazolyl ligands
    Aspinall, Helen C.
    Beckingham, Oliver
    Farrar, Michael D.
    Greeves, Nicholas
    Thomas, Christopher D.
    [J]. TETRAHEDRON LETTERS, 2011, 52 (40) : 5120 - 5123
  • [8] Copper-catalyzed oxidative sp3 C-H bond arylation with aryl boronic acids
    Basle, Olivier
    Li, Chao-Jun
    [J]. ORGANIC LETTERS, 2008, 10 (17) : 3661 - 3663
  • [9] Aerobic and Electrochemical Oxidative Cross-Dehydrogenative-Coupling (CDC) Reaction in an Imidazolium-Based Ionic Liquid
    Basle, Olivier
    Borduas, Nadine
    Dubois, Pauline
    Chapuzet, Jean Marc
    Chan, Tak-Hang
    Lessard, Jean
    Li, Chao-Jun
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (27) : 8162 - 8166
  • [10] Palladium-Catalyzed Oxidative sp2 C-H Bond Acylation with Aldehydes
    Basle, Olivier
    Bidange, Johan
    Shuai, Qi
    Li, Chao-Jun
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (07) : 1145 - 1149
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