Hypoiodite-mediated metal-free catalytic aziridination of alkenes

Akira Yoshimura, Kyle R. Middleton, Chenjie Zhu, Victor N. Nemykin, Viktor Zhdankin

Research output: Contribution to journalArticlepeer-review

52 Scopus citations

Abstract

Look, no metal: A metal-free catalytic procedure for aziridination of alkenes using tetrabutylammonium iodide as the catalyst, m-chloroperoxybenzoic acid (mCPBA) as the terminal oxidant, and N-aminophthalimide as the nitrenium precursor has been developed (see scheme; right: X-ray structure of one of the products). Control experiments suggests that the active oxidant is in situ generated hypoiodous acid (HIO).

Original languageEnglish (US)
Pages (from-to)8059-8062
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number32
DOIs
StatePublished - Aug 6 2012

Keywords

  • aziridination
  • hypoiodous acid
  • iodine
  • organocatalysis
  • oxidation

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