Synthesis of cyclic enones via direct palladium-catalyzed aerobic dehydrogenation of ketones

J Am Chem Soc. 2011 Sep 21;133(37):14566-9. doi: 10.1021/ja206575j. Epub 2011 Aug 29.

Abstract

α,β-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 cyclohexanones 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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Catalysis
  • Chemistry Techniques, Synthetic
  • Cyclohexanones / chemical synthesis
  • Cyclohexanones / chemistry
  • Hydrocarbons, Cyclic / chemical synthesis*
  • Hydrocarbons, Cyclic / chemistry
  • Ketones / chemical synthesis
  • Ketones / chemistry*
  • Oxygen / chemistry
  • Palladium / chemistry*

Substances

  • Cyclohexanones
  • Hydrocarbons, Cyclic
  • Ketones
  • Palladium
  • Oxygen