An α-Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung

Adriano Bauer, Giovanni Di Mauro, Jing Li, Nuno Maulide

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The reactivity of iodine(III) reagents towards nucleophiles is often associated with umpolung and cationic mechanisms. Herein, we report a general process converting a range of ketone derivatives into α-cyclopropanated ketones by oxidative umpolung. Mechanistic investigation and careful characterization of side products revealed that the reaction follows an unexpected pathway and suggests the intermediacy of non-classical carbocations.

Original languageEnglish
Pages (from-to)18208-18212
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number41
DOIs
Publication statusPublished - 2020 Oct 5

Keywords

  • amide activation
  • hypervalent iodine
  • non-classical carbocation
  • umpolung

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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