The Parikh-Doering reaction is a venerable oxidation reaction in organic synthesis and a representative member of DMSO-activated oxidation reactions e.g. Swern, Pfitzner-Moffatt and Corey-Kim. The Parikh-Doering reaction exclusively uses pyridine sulfur trioxide (Py.SO3) which contains a weak SO3-N(sp 2 ) complex which increases the reactivity of sulfur trioxide compared to N(sp 3 ) amine complex. However, this necessitates the addition of an N(sp 3 ) base to deprotonate the alkoxysulfonium ion intermediate to afford the key ylide intermediate to furnish a DMSO-based oxidation. Furthermore, the release of toxic pyridine could be avoided if an alternative sulfation process could be identified that incorporates a N(sp 3 ) base. Despite these challenges and various superseded oxidation reaction developments, the Parikh-Doering reaction finds widespread use in complex natural product synthesis due to the advantages of non-cryogenic temperatures required, operationally simple, but often requires high loadings and prolonged reaction time. We have recently discovered a novel sulfuryl group transfer reagent with improved organic solubility properties for sulfation of organic substrates, tributylsulfoammonium betaine (TBSAB). We identified TBSAB contains a novel N-S bond (not a dative complex as per Py-SO3) through single crystal X-ray crystallography. The use of TBSAB would be detrimental for purification purposes in this chemistry when not isolating a sulfated intermediate due to its enhanced lipophilicity. Therefore, we considered whether a similar commercially available reagent Et3N.SO3 complex could achieve both the desired sulfation of DMSO and release Et3N in situ to deprotonate the alkoxysulfonium ion with increased atom economy (Chart 1). Chart 1. The original report by Parikh and Doering and this work.