Gold- or Platinum-Catalyzed Synthesis of Sulfur Heterocycles: Access to Sulfur Ylides without Using Sacrificial Functionality


  • Financial support from the EPSRC (EP/EO32168/1) and the University of Birmingham is gratefully acknowledged. We thank Johnson Matthey plc for a loan of metal salts. This research was supported through Birmingham Science City: Innovative Uses for Advanced Materials in the Modern World (West Midlands Centre for Advanced Materials Project 2), with support from Advantage West Midlands (AWM) and by the European Regional Development Fund (ERDF).


original image

It′s no sacrifice: Alkynes have been used as direct precursors to sulfur ylides under gold or platinum π-acid catalysis in an atom-economic manner. An intramolecular redox reaction between an alkyne group with a tethered sulfoxide unit generates a sulfur ylide, which undergoes 2,3-sigmatropic rearrangement. Acyclic substrates are cycloisomerized to afford functionalized dihydrothiophenones (see scheme) and dihydrothiopyranones.