Visible-Light-Induced Aerobic Oxidation of Benzylic C(sp³)–H of Alkylarenes Promoted by DDQ, tert-Butyl Nitrite, and Acetic Acid

Abstract

A visible-light photocatalytic aerobic oxidation of benzylic C(sp³)–H bonds proceeded in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, tert-butyl nitrite, and acetic acid. Advantages of this aerobic oxidation method include its relatively mild conditions, the use of visible-light irradiation instead of conventional thermal methods, the use of a low catalyst loading, and the ability to oxidize a range of alkyl­arenes, including xanthenes, thioxanthenes, and 9,10-dihydroacridines, to the corresponding ketones in excellent yields.

Key words

xanthenones - thioxanthenones - acridinones - oxidation - photocatalysis - benzylic oxidation

• References and Notes

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