Catalytic oxidation of alkylbenzenes with molecular oxygen under normal pressure and temperature by N-hydroxyphthalimide combined with Co(OAc)(2)

被引:309
作者
Yoshino, Y
Hayashi, Y
Iwahama, T
Sakaguchi, S
Ishii, Y
机构
[1] KANSAI UNIV,FAC ENGN,DEPT APPL CHEM,SUITA,OSAKA 564,JAPAN
[2] KANSAI UNIV,HIGH TECHNOL RES CTR,SUITA,OSAKA 564,JAPAN
关键词
D O I
10.1021/jo9708147
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical catalytic method to convert alkylbenzenes into the corresponding carboxylic acids under atmospheric dioxygen at ambient temperature using a combined catalytic system consisting of N-hydroxyphthalimide (NHPI) and Co(OAc)(2) was developed. For instance, the oxidation of toluene was completed by NHPI combined with Co(OAc)(2) under an oxygen atmosphere at room temperature to give benzoic acid in 81% yield. Under these conditions, o- and p-xylenes were selectively converted into the corresponding monocarboxylic acids without the formation of the dicarboxylic acids. ESR measurements showed that Co(II) species assists in the formation of phthalimide-N-oxyl (PINO), which is a key species in this oxidation, from NHPI.
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页码:6810 / 6813
页数:4
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