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Hydroperoxidation of Tertiary Alkylaromatics Catalyzed By N-Hydroxyphthalimide and Aldehydes under Mild Conditions

✍ Scribed by Lucio Melone; Cristian Gambarotti; Simona Prosperini; Nadia Pastori; Francesco Recupero; Carlo Punta

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 350 KB
Volume: 353
Category: Article
ISSN: 1615-4150
DOI: 10.1002/adsc.201000786

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✦ Synopsis

Abstract

A metal‐free catalytic system consisting of an aldehyde and N‐hydroxyphthalimide (NHPI) for the selective oxidation of tertiary alkylaromatics with molecular oxygen has been developed. Cumene was oxidized efficiently to the corresponding hydroperoxide under mild conditions. The molecule‐induced homolysis between peracids generated in situ and NHPI ensured the formation of the phthalimide N‐oxyl (PINO) radical even at room temperature. Investigations on aldehyde, solvent and temperature effects allowed us to achieve good conversions with high selectivity in hydroperoxide. The optimized procedure was successfully extended to phenylcyclohexane, a valuable alternative for the production of phenol. The mechanism is discussed in detail.

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