Unique one step, multicomponent α,β,β-oxidations of carbamates with Willgerodt-like hypervalent iodine reagents - An example of triple C-H bond activation

Walter Salamant, Christopher Hulme

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

This communication reveals a novel multicomponent oxidation of saturated, urethane protected nitrogen heterocyclic systems. The oxidation is facile, general, high yielding and involves the application of readily-made hypervalent iodine reagents, giving an α,β,β-oxidation pattern relative to the nitrogen of the heterocycle. The oxidation is multicomponent type III, in that the substrate, reagent and solvent provide the three inputs during the reaction. The transformation also represents an example of triple C-H bond activation. A mechanistic rationale for this is proposed.

Original languageEnglish (US)
Pages (from-to)605-609
Number of pages5
JournalTetrahedron Letters
Volume47
Issue number4
DOIs
StatePublished - Jan 23 2006
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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