Ruthenium-catalyzed C-H/CO/olefin coupling reaction of N-arylpyrazoles.: Extraordinary reactivity of N-arylpyrazoles toward carbonylation at C-H bonds

被引:48
作者
Asaumi, T [1 ]
Chatani, N [1 ]
Matsuo, T [1 ]
Kakiuchi, F [1 ]
Murai, S [1 ]
机构
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
关键词
D O I
10.1021/jo0343127
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of 1-arylpyrazoles with CO and ethylene in the presence of Ru-3(CO)(12) resulted in regioselective carbonylation at the ortho C-H bonds. While it is found that the pyrazole ring also functions as the directing group for C-H bond cleavage, the efficiency of the reaction depends on the position of the pyrazole ring.
引用
收藏
页码:7538 / 7540
页数:3
相关论文
共 30 条
  • [1] ASAUMI T, UNPUB
  • [2] SPECTRA IONIZATION AND DEUTERIATION OF OXAZOLES AND RELATED COMPOUNDS
    BROWN, DJ
    GHOSH, PB
    [J]. JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1969, (03): : 270 - +
  • [3] Ru3(CO)12-catalyzed C-H/CO/olefin coupling of N-pyridylindolines.: Direct carbonylation at a C-H bond δ to the pyridine nitrogen
    Chatani, N
    Yorimitsu, S
    Asaumi, T
    Kakiuchi, F
    Murai, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) : 7557 - 7560
  • [4] Ru-3(CO)(12)-catalyzed reaction of pyridylbenzenes with carbon monoxide and olefins. Carbonylation at a C-H bond in the benzene ring
    Chatani, N
    Ie, Y
    Kakiuchi, F
    Murai, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) : 2604 - 2610
  • [5] Acylation of five-membered N-heteroaromatic compounds by ruthenium carbonyl-catalyzed direct carbonylation at a C-H bond
    Chatani, N
    Fukuyama, T
    Tatamidani, H
    Kakiuchi, F
    Murai, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (13) : 4039 - 4047
  • [6] Carbonylation at sp3 C-H bonds adjacent to a nitrogen atom in alkylamines catalyzed by rhodium complexes
    Chatani, N
    Asaumi, T
    Ikeda, T
    Yorimitsu, S
    Ishii, Y
    Kakiuchi, F
    Murai, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) : 12882 - 12883
  • [7] Ru-3(CO)(12)-catalyzed coupling of heteroaromatic C-H/CO/olefins. Regioselective acylation of the imidazole ring
    Chatani, N
    Fukuyama, T
    Kakiuchi, F
    Murai, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (02) : 493 - 494
  • [8] Ru3(CO)12- and Rh4(CO)12-catalyzed reactions of pyridylolefins or N-(2-pyridyl)enamines with CO and olefins.: Carbonylation at olefinic C-H bonds
    Chatani, N
    Ishii, Y
    Ie, Y
    Kakiuchi, F
    Murai, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15) : 5129 - 5136
  • [9] New synthetic method for the preparation of indenones from aromatic imines. Ru-3(CO)(12)-catalyzed carbonylation at an ortho C-H bond in the aromatic imines
    Fukuyama, T
    Chatani, N
    Kakiuchi, F
    Murai, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) : 5647 - 5650
  • [10] Ru3(CO)12-catalyzed site-selective carbonylation reactions at a C-H bond in aza-heterocycles
    Fukuyama, T
    Chatani, N
    Tatsumi, J
    Kakiuchi, F
    Murai, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (44) : 11522 - 11523