Assistant Professor Patrick R. Melvin, Students, and Alums Co-Author Article

Synthesis of Highly Reactive Sulfone Iminium Fluorides and Their Use in Deoxyfluorination and Sulfur Fluoride Exchange Chemistry

Authors: James A. Vogel, M.A. '21; Rania Hammami '22; Ara Ko '22; Hiya Datta '21; Yael N. Eiben '23; Karley J. Labenne '22; Ellis C. McCarver '21; Ebrar Z. Yilmaz '23; Patrick R. Melvin

Source: Organic Letters, Volume: 24, Issue: 32, Pages: 5962-5966, DOI: 10.1021/acs.orglett.2c02232, August 2022

Type of Publication: Article

Abstract: We report the synthesis of sulfone iminium fluorides (SIFs), a reactive class of sulfur(VI) molecules. The synthesis is tolerant of a variety of substituents on the sulfur and nitrogen components. The SIF reagents were applied to the deoxyfluorination of alcohols and carboxylic acids, providing high yields of fluorinated products in 60 s at room temperature. The SIF reagents were then utilized in sulfur fluoride exchange (SuFEx), creating the first ionic SuFEx products to date.

Patrick R. Melvin is an assistant professor of chemistry.