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
  • [1] REACTIVITY OF ORGANOPALLADIUM COMPOUNDS TOWARD MOLYBDENUM PEROXIDES - OXYGEN INSERTION VERSUS C-CL AND C-O COUPLING - EVIDENCE FOR PALLADIUM(IV) MOLYBDATE INTERMEDIATES
    ALSTERS, PL
    BOERSMA, J
    VANKOTEN, G
    [J]. ORGANOMETALLICS, 1993, 12 (05) : 1629 - 1638
  • [2] OXYGENATION OF CYCLOPALLADATED N,N-DIMETHYLBENZYLAMINE COMPLEXES BY INORGANIC AND ORGANIC PEROXIDES - OXYGEN INSERTION INTO THE PALLADIUM-CARBON BOND
    ALSTERS, PL
    TEUNISSEN, HT
    BOERSMA, J
    SPEK, AL
    VANKOTEN, G
    [J]. ORGANOMETALLICS, 1993, 12 (11) : 4691 - 4696
  • [3] Mechanistic studies on the hydroxylation of methane by methane monooxygenase
    Baik, MH
    Newcomb, M
    Friesner, RA
    Lippard, SJ
    [J]. CHEMICAL REVIEWS, 2003, 103 (06) : 2385 - 2419
  • [4] Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature
    Boele, MDK
    van Strijdonck, GPF
    de Vries, AHM
    Kamer, PCJ
    de Vries, JG
    van Leeuwen, PWNM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) : 1586 - 1587
  • [5] Selective catalytic hydroxylation of a steroid by an artificial cytochrome P-450 enzyme
    Breslow, R
    Zhang, XJ
    Huang, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (19) : 4535 - 4536
  • [6] Total synthesis of eudesmane terpenes by site-selective C-H oxidations
    Chen, Ke
    Baran, Phil S.
    [J]. NATURE, 2009, 459 (7248) : 824 - 828
  • [7] A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis
    Chen, Mark S.
    White, M. Christina
    [J]. SCIENCE, 2007, 318 (5851) : 783 - 787
  • [8] Serial ligand catalysis: A highly selective allylic C-H oxidation
    Chen, MS
    Prabagaran, N
    Labenz, NA
    White, MC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) : 6970 - 6971
  • [9] Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter
    Chen, X
    Li, JJ
    Hao, XS
    Goodhue, CE
    Yu, JQ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) : 78 - 79
  • [10] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant
    Chen, Xiao
    Hao, Xue-Shi
    Goodhue, Charles E.
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) : 6790 - 6791