Get access

Nucleophilic ortho-Propargylation of Aryl Sulfoxides: An Interrupted Pummerer/Allenyl Thio-Claisen Rearrangement Sequence


  • We thank Merck Sharp & Dohme (CASE award to A.E.) and the EPSRC (CPhD award to A.E.).


original image

A new direction: The nucleophilic ortho-propargylation of aryl sulfoxides exploits intermolecular delivery of the nucleophile to sulfur followed by an intramolecular relay to carbon (see scheme). The simple, metal-free procedure is general, regiospecific with regard to the propargyl nucleophile, and completely selective for products of ortho-propargylation over allenylation.