Researcher ORCID Identifier
https://orcid.org/0009-0002-7581-2065
Graduation Year
2026
Document Type
Campus Only Senior Thesis
Degree Name
Bachelor of Arts
Department
Chemistry
Reader 1
Nicholas Ball
Reader 2
Roberto Garza
Terms of Use & License Information
Rights Information
© 2026 Joseph R Novicki & Nicholas Ball
Abstract
Sulfur(VI)-containing functional groups, particularly sulfonamides and sulfones, are widely represented in modern pharmaceuticals due to their metabolic stability, structural diversity, and favorable physicochemical properties. Sulfur fluoride exchange (SuFEx) has emerged as a powerful “click” reaction for constructing sulfur(VI) linkages through nucleophilic substitution at electrophilic sulfur centers. More recently, sulfur–phenolate exchange (SuPhenEx) has been developed as a complementary fluorine-free strategy that replaces fluoride with an activated phenolate leaving group, improving sustainability while maintaining efficiency.
Although SuFEx and SuPhenEx proceed through similar mechanisms, their tandem integration in small-molecule synthesis remains largely unexplored. This work proposes a telescoped one-pot SuFEx/SuPhenEx strategy for the synthesis of α-amidosulfonamides from bifunctional fluorosulfate substrates. In this approach, the sulfur–fluoride handle first undergoes SuFEx with a trimethylsilyl-protected amine under catalytic Lewis acid conditions. The activated phenolate handle then participates in SuPhenEx with a carbon-based pronucleophile, to afford an α-amidosulfonamide scaffold in a single operational method.
Recommended Citation
Novicki, Joseph R. and Ball, Nicholas, "Telescoping SuPhenEx and SuFEx Reactions for the One- Pot Synthesis of 𝜶-amidosulfonamides" (2026). Pomona Senior Theses. 377.
https://scholarship.claremont.edu/pomona_theses/377
This thesis is restricted to the Claremont Colleges current faculty, students, and staff.
