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Homobenzylic Oxygenation Enabled by Dual Organic Photoredox and Cobalt Catalysis

Joshua B. McManus, Jeremy D. Griffin, Alexander R. White and David A. Nicewicz*

*Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States, Email: nicewiczunc.edu

J. B. McManus, J. D. Griffin, A. R. White, D. A. Nicewicz, J. Am. Chem. Soc., 2020, 142, 10325-10330.

DOI: 10.1021/jacs.0c04422 (free Supporting Information)


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Abstract

Reactivity at the homobenzylic position can be accomplished using dual organic photoredox/cobalt catalysis. Through a two-part catalytic system, alkyl arenes undergo dehydrogenation followed by an anti-Markovnikov Wacker-type oxidation to provide benzyl ketone products. This formal homobenzylic oxidation is accomplished with high atom economy without the use of directing groups.

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Key Words

ketones, benzylic oxidation, photochemistry


ID: J48-Y2020