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Preparation of Hydroperoxides by N ‐Hydroxyphthalimide‐Catalyzed Aerobic Oxidation of Alkylbenzenes and Hydroaromatic Compounds and Its Application
Author(s) -
Fukuda Osamu,
Sakaguchi Satoshi,
Ishii Yasutaka
Publication year - 2001
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(20011231)343:8<809::aid-adsc809>3.0.co;2-1
Subject(s) - alkylbenzenes , chemistry , phenol , phenols , catalysis , organic chemistry , benzaldehyde , cumene , aldehyde , yield (engineering) , materials science , metallurgy
An efficient approach to phenols and aldehydes through the formation of hydroperoxides from alkylbenzenes was successfully achieved by aerobic oxidation using N ‐hydroxyphthalimide (NHPI) as a catalyst. The oxidation of various alkylbenzenes with dioxygen by NHPI followed by treatment with a Lewis acid or triphenylphosphine led to phenols or aldehydes, respectively, in good yields. For example, the aerobic oxidation of cumene in the presence of a catalytic amount of NHPI at 75 °C and subsequent treatment with H 2 SO 4 gave phenol in 77% yield. 1,4‐Dihydroxybenzene (61%) and 4‐isopropylphenol (33%) were obtained from 1,4‐diisopropylbenzene. On the other hand, dibenzyl ether was converted into phenol or benzaldehyde upon treatment of the resulting hydroperoxide with InCl 3 or PPh 3 , respectively.