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 [J].
BROWN, DJ ;
GHOSH, PB .
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 [J].
Chatani, N ;
Yorimitsu, S ;
Asaumi, T ;
Kakiuchi, F ;
Murai, S .
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 [J].
Chatani, N ;
Ie, Y ;
Kakiuchi, F ;
Murai, S .
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 [J].
Chatani, N ;
Fukuyama, T ;
Tatamidani, H ;
Kakiuchi, F ;
Murai, S .
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 [J].
Chatani, N ;
Asaumi, T ;
Ikeda, T ;
Yorimitsu, S ;
Ishii, Y ;
Kakiuchi, F ;
Murai, S .
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 [J].
Chatani, N ;
Fukuyama, T ;
Kakiuchi, F ;
Murai, S .
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 [J].
Chatani, N ;
Ishii, Y ;
Ie, Y ;
Kakiuchi, F ;
Murai, S .
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 [J].
Fukuyama, T ;
Chatani, N ;
Kakiuchi, F ;
Murai, S .
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 [J].
Fukuyama, T ;
Chatani, N ;
Tatsumi, J ;
Kakiuchi, F ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (44) :11522-11523