Oxidation Adjacent to C X Bonds by Dehydrogenation

S. S. Stahl, T. Diao

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

α,β-Unsaturated carbonyl compounds are versatile intermediates in the synthesis of pharmaceuticals and biologically active compounds. This chapter summarizes different oxidation methods available for dehydrogenation adjacent to carbonyl groups to access α,β-unsaturated carbonyl compounds. Historically important stoichiometric methods include sequential halogenation/dehydrohalogenation, elimination reactions that use sulfur and selenium reagents, and dichlorodicyanoquinone (DDQ)-mediated dehydrogenation. The use of hypervalent iodine reagents, such as 2-iodoxybenzoic acid (IBX), in α,β-dehydrogenation reactions has grown significantly, as have catalytic dehydrogenation methods, such as Pd-catalyzed methods capable of O2 or other desirable stoichiometric oxidants. An overview of each of these methods is presented, together with selected synthetic applications. The relative merits of the individual methods are also considered.

Original languageEnglish (US)
Title of host publicationComprehensive Organic Synthesis
Subtitle of host publicationSecond Edition
PublisherElsevier Ltd
Pages178-212
Number of pages35
Volume7
ISBN (Print)9780080977430
DOIs
StatePublished - Feb 2014

Keywords

  • Aerobic
  • Carbonyl Compounds
  • Dehydrogenation
  • Enone
  • Hypervalent iodine
  • Pd catalysis
  • α,β-Unsaturation

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Fingerprint Dive into the research topics of 'Oxidation Adjacent to C X Bonds by Dehydrogenation'. Together they form a unique fingerprint.

  • Cite this

    Stahl, S. S., & Diao, T. (2014). Oxidation Adjacent to C X Bonds by Dehydrogenation. In Comprehensive Organic Synthesis: Second Edition (Vol. 7, pp. 178-212). Elsevier Ltd. https://doi.org/10.1016/B978-0-08-097742-3.00707-2