Graduation Year


Document Type

Campus Only Senior Thesis

Degree Name

Bachelor of Arts



Reader 1

Nicholas D. Ball

Reader 2

Matthew H. Sazinsky

Terms of Use & License Information

Terms of Use for work posted in Scholarship@Claremont.

Rights Information

© 2024 Matt Teeter


Sulfur(IV)-containing molecules are of great interest to chemists and can be found in a wide array of agrochemicals, pharmaceuticals, and materials.In addition, S(VI) motifs have been shown to be valuable tools in organic synthesis, with S(VI)-fluorides serving as hubs for connecting molecular building blocks in the synthesis of complex products through sulfur-fluorine exchange (SuFEx) reactions. S(VI)-fluorides are attractive starting materials due to the latent reactivity of the S-F bond, which can remain unreacted in the course of a larger synthesis but can be activated for nucleophilic attack under certain conditions, usually by a Lewis acid. Typical SuFEx reactions involve a nitrogen or oxygen nucleophile, forming sulfonamides or sulfonate esters, respectively, but reactions with carbon nucleophiles have not been well-explored. Those which have been elucidated are limited in their applicability due to harsh reaction conditions.

In collaboration with our colleagues at Pfizer, a SuFEx sulfonylation reaction which makes use of a methyl ester enolate nucleophile to form alkyl aryl sulfones is presented. Notably, these conditions are carried out in one pot, and there is preliminary evidence that suggests that a variety of functional groups are tolerated. In addition, the reaction proceeds through an α-ester sulfone intermediate, which is then decarboxylated to yield the sulfone product; this intermediate structural motif is relatively unexplored, and this synthetic route constitutes a novel approach to the synthesis of sulfones. However, yields of this intermediate remain a challenge, and investigating the addition step of the reaction through enolization studies and the role of metal counterions, such as lithium and calcium, in the activation of the S-F bond for nucleophilic attack will help to improve the proposed conditions. In addition, a broad substrate scope will help to demonstrate the applicability of these conditions.

Available for download on Monday, April 21, 2025

This thesis is restricted to the Claremont Colleges current faculty, students, and staff.