Concerning the mechanism of the FeCl3-catalyzed α-oxyamination of aldehydes: Evidence for a non-SOMO activation pathway

Jeffrey F. Van Humbeck, Scott P. Simonovich, Robert R. Knowles, David W.C. MacMillan

Research output: Contribution to journalArticle

114 Scopus citations

Abstract

The mechanism of a recently reported aldehyde α-oxyamination reaction has been studied using a combination of kinetic, spectrometric, and spectrophotometric techniques. Most crucially, the use of a validated cyclopropane-based radical-clock substrate has demonstrated that carbon-oxygen bond formation occurs predominantly through an enamine activation manifold. The mechanistic details reported herein indicate that, as has been proposed for previously studied alcohol oxidations, complexation between TEMPO and a simple metal salt leads to electrophilic ionic reactivity.

Original languageEnglish (US)
Pages (from-to)10012-10014
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number29
DOIs
StatePublished - Jul 28 2010

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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