Pd(II)-Catalyzed Hydroxylation of Arenes with 1 atm of O2 or Air

被引:380
作者
Zhang, Yang-Hui [1 ]
Yu, Jin-Quan [1 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
基金
美国国家科学基金会;
关键词
C-H BONDS; OXYGEN INSERTION; OXIDATION; BENZOQUINONE; ACTIVATION; PEROXIDES; COMPLEXES; MECHANISM; DIOXYGEN; METHANOL;
D O I
10.1021/ja907198n
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pd(II)-catalyzed ortho-hydroxylation of variously substituted benzoic acids under 1 atm of O-2 or air is achieved under nonacidic conditions. Extensive labeling studies support a direct oxygenation of aryl C-H bonds with molecular oxygen.
引用
收藏
页码:14654 / +
页数:3
相关论文
共 41 条
  • [31] PIERA J, 2008, ANGEW CHEM INT EDIT, V47, P2
  • [32] Chiral Mn-salen catalyzed enantiotopic selective C-H oxidation of meso-pyrrolidine derivatives
    Punniyamurthy, T
    Miyafuji, A
    Katsuki, T
    [J]. TETRAHEDRON LETTERS, 1998, 39 (45) : 8295 - 8298
  • [33] Biologically inspired oxidation catalysis
    Que, Lawrence, Jr.
    Tolman, William B.
    [J]. NATURE, 2008, 455 (7211) : 333 - 340
  • [34] Structural and mechanistic investigations of the oxidation of dimethylplatinum(II) complexes by dioxygen
    Rostovtsev, VV
    Henling, LM
    Labinger, JA
    Bercaw, JE
    [J]. INORGANIC CHEMISTRY, 2002, 41 (14) : 3608 - 3619
  • [35] Activation of C-H bonds by metal complexes
    Shilov, AE
    Shul'pin, GB
    [J]. CHEMICAL REVIEWS, 1997, 97 (08) : 2879 - 2932
  • [36] Ortho-hydroxylation of benzoic acids with hydrogen peroxide at a non-heme iron center
    Taktak, S
    Flook, M
    Foxman, BM
    Que, L
    Rybak-Akimova, EV
    Akimova, R
    [J]. CHEMICAL COMMUNICATIONS, 2005, (42) : 5301 - 5303
  • [37] Towards Photocatalytic Alkane Oxidation: The Insertion of Dioxygen into a Platinum (II)-Methyl Bond
    Taylor, Russell A.
    Law, David J.
    Sunley, Glenn J.
    White, Andrew J. P.
    Britovsek, George J. P.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (32) : 5900 - 5903
  • [38] Stoichiometric aerobic PtII-Me bond cleavage in aqueous solutions to produce methanol and a PtII(OH) complex
    Vedernikov, AN
    Binfield, SA
    Zavalij, PY
    Khusnutdinova, JR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) : 82 - 83
  • [39] Ligand-enabled PtII-C(sp3) bond functionalization with dioxygen as a direct oxidant
    Vedernikov, Andrei N.
    [J]. CHEMICAL COMMUNICATIONS, 2009, (32) : 4781 - 4790
  • [40] Regioselective intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in situ
    Yang, D
    Wong, MK
    Wang, XC
    Tang, YC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) : 6611 - 6612