Molecular Iodine‐Mediated Functionalization of α‐Carbonyl Sulfoxonium Ylides with Thiocyanates, Xanthates, and Dithiocarbamates

Abstract

In this work, a straightforward, rapid, and cost‐effective protocol is presented for synthesizing three distinct classes of α‐functionalized sulfoxonium ylides—α‐xanthate, α‐thiocyanate, and α‐dithiocarbamate—via molecular iodine‐mediated reactions. This method demonstrates broad substrate tolerance, including heterocycles and steroids, delivering 25 examples with yields of up to 83%. Experimental studies revealed that iodine reacts with xanthates to form disulfides, which subsequently act as electrophiles for nucleophilic attack by the ylide.