Synthesis of Highly Reactive Sulfone Iminium Fluorides and Their Use in Deoxyfluorination and Sulfur Fluoride Exchange Chemistry
Author: Vogel, James A.; Hammami, Rania; Ko, Ara; Datta, Hiya; Eiben, Yael N.; Labenne, Karley J.; McCarver, Ellis C.; Yilmaz, Ebrar Z.; Melvin, Patrick R.
Source: American Chemical Society, Org. Lett. 2022, 24, 32, 5962–5966, DOI: 10.1021/acs.orglett.2c02232, August 2022
Type of Publication: Article in a Periodical
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.