Ruthenium-catalyzed O- to S-alkyl migration: a pseudoreversible Barton-McCombie pathway

William Mahy, Pawel Plucinski, Jesús Jover, Christopher G. Frost

Research output: Contribution to journalArticle

9 Citations (Scopus)
75 Downloads (Pure)

Abstract

A practical ruthenium-catalyzed O- to S-alkyl migration affords structurally diverse thiooxazolidinones in excellent yields. Our studies suggest this catalytic transformation proceeds through a pseudoreversible radical pathway drawing mechanistic parallels to the classic Barton-McCombie reaction. A radical step in a new direction: A practical ruthenium-catalyzed O- to S-alkyl migration affords structurally diverse thiooxazolidinones in excellent yields. Experimental and computational studies suggest a pseudoreversible radical pathway drawing mechanistic parallels to the classic Barton-McCombie reaction.

Original languageEnglish
Pages (from-to)10944-10948
Number of pages5
JournalAngewandte Chemie-International Edition
Volume54
Issue number37
DOIs
Publication statusPublished - 7 Sep 2015

    Fingerprint

Keywords

  • alkyl migration
  • Barton-McCombie reaction
  • catalysis
  • O-thiocarbamates
  • pseudoreversible reaction

Cite this