Ruthenium-Catalyzed O- to S-Alkyl Migration: A Pseudoreversible Barton-McCombie Pathway

William Mahy; Pawel Plucinski; Jesús Jover; Christopher G Frost

doi:10.1002/anie.201505280

Ruthenium-Catalyzed O- to S-Alkyl Migration: A Pseudoreversible Barton-McCombie Pathway

Angew Chem Int Ed Engl. 2015 Sep 7;54(37):10944-8. doi: 10.1002/anie.201505280. Epub 2015 Jul 27.

Authors

William Mahy¹, Pawel Plucinski², Jesús Jover³, Christopher G Frost⁴

Affiliations

¹ Department of Chemistry, University of Bath, Bath, BA2 7AY (UK).
² Department of Chemical Engineering, University of Bath, Bath, BA2 7AY (UK).
³ Departament de Química Inorgànica, Universitat de Barcelona, C/Martí i Franquès 1-11, 08028 Barcelona (Spain).
⁴ Department of Chemistry, University of Bath, Bath, BA2 7AY (UK). c.g.frost@bath.ac.uk.

PMID: 26223389
DOI: 10.1002/anie.201505280

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.

Keywords: Barton-McCombie reaction; O-thiocarbamates; alkyl migration; catalysis; pseudoreversible reaction.

MeSH terms

Catalysis
Ruthenium / chemistry*

Substances

Ruthenium