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

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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

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Ruthenium
Direction compound

Keywords

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

Cite this

Ruthenium-catalyzed O- to S-alkyl migration : a pseudoreversible Barton-McCombie pathway. / Mahy, William; Plucinski, Pawel; Jover, Jesús; Frost, Christopher G.

In: Angewandte Chemie-International Edition, Vol. 54, No. 37, 07.09.2015, p. 10944-10948.

Research output: Contribution to journalArticle

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