Metal Free Amino-Oxidation of Electron Rich Alkenes Mediated by an Oxoammonium Salt

Alexandra M. Millimaci, Rowan I.L. Meador, Sara J. Dampf, John D. Chisholm

Research output: Contribution to journalArticlepeer-review

Abstract

4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate (Bobbitt's salt) effectively activates electron rich alkenes and promotes the addition of anilines. This transformation provides a direct, transition metal free method for amino-oxidation of alkenes under mild conditions. The relative stereochemistry of the amino-oxidation is influenced by solvent effects, with both the syn and anti amino-oxidation products being accessible from identical starting materials.

Original languageEnglish (US)
Pages (from-to)322-326
Number of pages5
JournalIsrael Journal of Chemistry
Volume61
Issue number5-6
DOIs
StatePublished - May 2021

Keywords

  • alkenes
  • amination
  • oxidation
  • oxoammonium
  • regioselective

ASJC Scopus subject areas

  • Chemistry(all)

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