Relative to alkene dihydroxylation, alkene disulfonoxylation remains less explored (Scheme 1). As diols are often subsequently converted into the corresponding tosylates or mesylates, one step syntheses of such compounds from alkene starting materials would be desirable from the perspective of step economy and reagent waste. Existing protocols for disulfonoxylation have greatly inspired this study and most employ the use of hypervalent iodine reagents, which are convenient alternatives to toxic metals such as osmium. Despite these positive features, literature reactions suffer from several drawbacks. These include the use of excess alkene, extended reaction times, narrow substrate scope with respect to both the alkene substrate and the sulfonic acid partner, and a reliance on non-commercial reagents. The work presented here addresses these limitations.