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

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.