Iodine(III)-catalyzed benzylic oxidation by using the (PhIO)n/Al(NO3)3 system

被引:22
|
作者
Yahuaca-Juarez, Berencie [1 ]
Gonzalez, Gerardo [2 ]
Ramirez-Morales, Marco A. [2 ]
Alba-Betancourt, Calara [2 ]
Deveze-Alvarez, Martha A. [2 ]
Mendoza-Macias, Claudia L. [2 ]
Ortiz-Alvarado, Rafael [1 ]
Juarez-Ornelas, Kevin A. [2 ]
Solorio-Alvarado, Cesar R. [2 ]
Maruoka, Keiji [3 ,4 ]
机构
[1] Univ Michoacana, Fac Quim Farmacobiol, Morelia, Michoacan, Mexico
[2] Univ Guanajuato, Dept Quim, Divi Ciencias Nat & Exactas, Guanajuato, Mexico
[3] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto, Japan
[4] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Peoples R China
关键词
Benzylic oxidation; C-sp(3)-H activation; iodine(III)-catalysis; organocatalyst; C-H OXIDATION; AEROBIC OXIDATION; EFFICIENT; METAL; BROMINATION; TETRALIN; REAGENT; PHENOLS; COPPER; BONDS;
D O I
10.1080/00397911.2019.1707225
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first iodine(III)-based procedure for the benzylic oxidation of different arenes is described by using the (PhIO)(n)/Al(NO3)(3) system under catalytic conditions leading to the formation of the corresponding carbonyl derivatives. The method proceeds under mild, operationally simple, room temperature, short reaction times, and open flask conditions. In light of the organocatalysis relevance and the novelty of our protocol, we wish to communicate our initial results of this novel oxidation.
引用
收藏
页码:539 / 548
页数:10
相关论文
共 50 条
  • [41] Intramolecular C(sp3)-N Coupling by Oxidation of Benzylic C,N-Dianions
    Jeffrey, Jenna L.
    Bartlett, Emily S.
    Sarpong, Richmond
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (08) : 2194 - 2197
  • [42] Fe(NO3)3-Catalyzed Monoterpene Oxidation by Hydrogen Peroxide: An Inexpensive and Environmentally Benign Oxidative Process
    Carari, Danieli Marcolan
    da Silva, Marcio Jose
    CATALYSIS LETTERS, 2014, 144 (04) : 615 - 622
  • [43] Gold(III)-Catalyzed Decarboxylative C3-Benzylation of Indole-3-carboxylic Acids with Benzylic Alcohols in Water
    Hikawa, Hidemasa
    Kotaki, Fumiya
    Kikkawa, Shoko
    Azumaya, Isao
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (04): : 1972 - 1979
  • [44] Phase Diagram for the System Cu(NO3)2-Al(NO3)3-H2O Ternary System Between 10 and 50 °C
    Barroug, A.
    Laallam, L.
    Boulghallat, M.
    Jouaiti, A.
    JOURNAL OF PHASE EQUILIBRIA AND DIFFUSION, 2012, 33 (04) : 310 - 314
  • [45] Air Oxidation of Sulfides to Sulfoxides Using BiBr3-@Bi(NO3)3 as a Binary Catalyst
    Komatsu, N.
    Uda, M.
    Suzuki, H.
    Chemistry Letters, 1997, (12)
  • [46] Phase Diagram for the System Cu(NO3)2-Al(NO3)3-H2O Ternary System Between 10 and 50 °C
    A. Barroug
    L. Lâallam
    M. Boulghallat
    A. Jouaiti
    Journal of Phase Equilibria and Diffusion, 2012, 33 : 310 - 314
  • [47] Air oxidation of sulfides to sulfoxides using BiBr3-Bi(NO3)3 as a binary catalyst
    Komatsu, N
    Uda, M
    Suzuki, H
    CHEMISTRY LETTERS, 1997, (12) : 1229 - 1230
  • [48] AL(IO3)3-AL(NO3)3-H2O SYSTEM AT 25-DEGREES-C
    SHKLOVSKAYA, RM
    ARKHIPOV, SM
    KIDYAROV, BI
    DAMINOVA, TV
    KUZINA, VA
    ZHURNAL NEORGANICHESKOI KHIMII, 1985, 30 (07): : 1857 - 1859
  • [49] Synthesis and structural characterization of the first europium(III) pyridylphosphine complex, [Eu(N,N′,N"-2-Py3P)(NO3)3]
    Artem'ev, Alexander V.
    Gusarova, Nina K.
    Malysheva, Svetlana F.
    Kazheva, Olga N.
    Alexandrov, Grigorii G.
    Dyachenko, Oleg A.
    Trofimov, Boris A.
    MENDELEEV COMMUNICATIONS, 2012, 22 (06) : 294 - 296
  • [50] Oxidation of Zinc Sulfide in the System HNO3-Fe(NO3)3-H2O
    S. V. Ostanova
    A. V. Chubarov
    S. V. Drozdov
    V. V. Patrushev
    Russian Journal of Applied Chemistry, 2002, 75 : 1354 - 1356