Document Type
Article
Version
Author's Final Manuscript
Publication Title
Organic Letters
Volume
24
Publication Date
2022
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.
Citation
Vogel, J. A., Hammami, R., Ko, A., Datta, H., Eiben, Y. N., Labenne, K. J., McCarver, E. C., Yilmaz, E. Z., and P. R. Melvin. 2022. "Synthesis of Highly Reactive Sulfone Iminium Fluorides and Their Use in Deoxyfluorination and Sulfur Fluoride Exchange Chemistry." Organic Letters 24.32: 5962-5966.
DOI
https://doi.org/10.1021/acs.orglett.2c02232