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

TitleSynthesis of Cyclic Enones via Direct Palladium-Catalyzed Aerobic Dehydrogenation of Ketones
Publication TypeJournal Article
Year of Publication2011
AuthorsDiao, T, Stahl, SS
JournalJournal of the American Chemical Society
Volume133
Pagination14566-14569
Date PublishedSep
Accession NumberWOS:000295148100026
Keywordsalcohol, aldehydes, alpha,beta-unsaturated carbonyl-compounds, c-h, chemistry, functionalization, ITO Y, 1978, JOURNAL OF ORGANIC CHEMISTRY, V43, P1011, molecular-oxygen, organoselenium reagents, oxidation, palladium(ii)-catalyzed oxidation, saegusa oxidation, selective oxidation, silyl enol ethers, Trost BM, 2010, CHEMISTRY-A EUROPEAN JOURNAL, V16, P6265, VRIES JG, 2007, HDB HOMOGENEOUS HYDR,
Abstract

alpha,beta-Unsaturated carbonyl compounds are versatile intermediates in the synthesis of pharmaceuticals and biologically active compounds. Here, we report the discovery and application of Pd(DMSO)(2)(TFA)(2) as a catalyst for direct dehydrogenation of cydohexanones and other cyclic ketones to the corresponding enones, using O(2) as the oxidant. The substrate scope includes heterocyclic ketones and several natural-product precursors.

Short TitleJ. Am. Chem. Soc.