Highly regioselective catalytic oxidative coupling reactions: Synthetic and mechanistic investigations

被引:327
作者
Hull, Kami L. [1 ]
Lanni, Erica L. [1 ]
Sanford, Melanie S. [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
关键词
D O I
10.1021/ja065718e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly efficient and regioselective Pd-catalyzed method for the oxidative coupling of arylpyridine derivatives is reported. Remarkably, the reactions proceed at room temperature and are compatible with diverse functionalities, including aryl halides and thiophenes. Mechanistic studies suggest that these transformations proceed via a previously unprecedented mechanism involving two different pyridine-directed C-H activation reactions-one at a PdII center and one at PdIV. Copyright © 2006 American Chemical Society.
引用
收藏
页码:14047 / 14049
页数:3
相关论文
共 25 条
  • [1] Arene C-H bond activation and arene oxidative coupling by cationic palladium(II) complexes
    Ackerman, LJ
    Sadighi, JP
    Kurtz, DM
    Labinger, JA
    Bercaw, JE
    [J]. ORGANOMETALLICS, 2003, 22 (19) : 3884 - 3890
  • [2] Biphasic oxidation of arenes with oxygen catalysed by Pd(II)-heteropoly acid system: oxidative coupling versus hydroxylation
    Burton, HA
    Kozhevnikov, IV
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 185 (1-2) : 285 - 290
  • [3] Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions
    Campeau, LC
    Parisien, M
    Jean, A
    Fagnou, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) : 581 - 590
  • [4] METAL-ION DEPENDENT REACTIVITY OF 2-(2'-THIENYL)PYRIDINE (HTHPY)
    CONSTABLE, EC
    SOUSA, LR
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 427 (01) : 125 - 139
  • [5] Anilide ortho-arylation by using C-H activation methodology
    Daugulis, O
    Zaitsev, VG
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) : 4046 - 4048
  • [6] Oxone as an inexpensive, safe, and environmentally benign oxidant for C-H bond oxygenation
    Desai, LV
    Malik, HA
    Sanford, MS
    [J]. ORGANIC LETTERS, 2006, 8 (06) : 1141 - 1144
  • [7] Palladium-catalyzed oxygenation of unactivated sp3 C-H bonds
    Desai, LV
    Hull, KL
    Sanford, MS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) : 9542 - 9543
  • [8] Unusually stable palladium(IV) complexes: Detailed mechanistic investigation of C-O bond-forming reductive elimination
    Dick, AR
    Kampf, JW
    Sanford, MS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (37) : 12790 - 12791
  • [9] A highly selective catalytic method for the oxidative functionalization of C-H bonds
    Dick, AR
    Hull, KL
    Sanford, MS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) : 2300 - 2301
  • [10] Pd-catalyzed stereoselective oxidation of methyl groups by inexpensive oxidants under mild conditions: A dual role for carboxylic anhydrides in catalytic C-H bond oxidation
    Giri, R
    Liang, J
    Lei, JG
    Li, JJ
    Wang, DH
    Chen, X
    Naggar, IC
    Guo, CY
    Foxman, BM
    Yu, JQ
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (45) : 7420 - 7424