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

Authors

James A. Vogel, Bryn Mawr College
Rania Hammami, Bryn Mawr College
Ara Ko, Bryn Mawr College
Hiya Datta, Bryn Mawr College
Yael N. Eiben, Bryn Mawr College
Karley J. Labenne, Bryn Mawr College
Ellis C. McCarver, Bryn Mawr College
Ebrar Z. Yilmaz, Bryn Mawr College
Patrick R. Melvin, Bryn Mawr CollegeFollow

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