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Synthesis of Cyclic Enones via Direct Palladium-Catalyzed Aerobic Dehydrogenation of Ketones

Tianning Diao and Shannon S. Stahl*

*Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States, Email: stahlchem.wisc.edu

T. Diao, S. S. Stahl, J. Am. Chem. Soc., 2011, 133, 14566-14569.

DOI: 10.1021/ja206575j (free Supporting Information)


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Abstract

Pd(DMSO)2(TFA)2 as a catalyst enables a direct dehydrogenation of cyclohexanones and other cyclic ketones to the corresponding enones, using O2 as the oxidant. α,β-Unsaturated carbonyl compounds are versatile intermediates in the synthesis of pharmaceuticals and biologically active compounds. The substrate scope includes heterocyclic ketones and several natural-product precursors.

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Key Words

Cyclohexenones, Enones, Oxygen


ID: J48-Y2011-2670