Ruthenium- and rhodium-catalyzed direct carbonylation of the ortho C-H bond in the benzene ring of N-arylpyrazoles

被引：68

作者：

Asaumi, T ^{[1
]}

Matsuo, T ^{[1
]}

Fukuyama, T ^{[1
]}

Ie, Y ^{[1
]}

Kakiuchi, F ^{[1
]}

Chatani, N ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 13期

关键词：

D O I：

10.1021/jo049864j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct carbonylation of C-H bonds in the benzene ring of N-phenylpyrazoles via catalysis by ruthenium or rhodium complexes is described. The reaction of N-phenylpyrazoles with carbon monoxide and ethylene in the presence of Ru-3(CO)(12) or Rh-4(CO)(12) resulted in the site-selective carbonylation of the ortho C-H bonds in the benzene ring to give the corresponding ethyl ketones. A variety of functional groups on the benzene ring can be tolerated. N-Phenylpyrazoles have higher reactivities than would be expected, based on the pK(a) values of the conjugate acid of pyrazole. The choice of solvent for this reaction is significant, and N,N-dimethylacetamide (DMA) gives the best result.

引用

页码：4433 / 4440

页数：8

共 56 条

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