Acyl-Ethynylbenziodoxolone (acyl-EBX): Access to Ketene Dithioarylacetals

Abstract

We report the synthesis of ketene dithioarylacetals in 40–97% yield using thiophenols and acyl-EBXs (ethynylbenziodoxolones) generated in situ from a common hypervalent iodine precursor and alkynyl trifluoroborate salts. The products could be further modified to afford functionalized ketene dithioacetals and various S-substituted heterocycles.

Synthesis of β,β-Dithioketones by Merging C–C and C–S Bond Cleavage in [1 + 1 + 1 + 1 + 1 + 1] Annulation

“…Limited examples were achieved by using premodified, unappealing 1,3dithiols and an additional C1 synthon (Scheme 1B). 7 Nevertheless, step-saving and user-friendly methods for the functionalization of 1,3-dithiane under mild conditions at specific low-activity reaction sites remain elusive.…”