Elemental Sulfur-Mediated Transformation of Carboxylic Acids to Acyl Fluorides by Electrophilic Fluorinating Reagent, Selectfluor

Elsayed M Mahmoud; Soichiro Mori; Yuji Sumii; Norio Shibata

doi:10.1021/acs.orglett.3c00701

Elemental Sulfur-Mediated Transformation of Carboxylic Acids to Acyl Fluorides by Electrophilic Fluorinating Reagent, Selectfluor

Org Lett. 2023 Apr 28;25(16):2810-2814. doi: 10.1021/acs.orglett.3c00701. Epub 2023 Apr 3.

Authors

Elsayed M Mahmoud^{1

2}, Soichiro Mori³, Yuji Sumii¹, Norio Shibata^{1

3}

Affiliations

¹ Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-Ku, Nagoya 466-8555, Japan.
² Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig 44519, Egypt.
³ Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-Ku, Nagoya 466-8555, Japan.

PMID: 37010934
DOI: 10.1021/acs.orglett.3c00701

Abstract

The elemental sulfur-mediated synthesis of acyl fluorides from carboxylic acids is achieved using Selectfluor. A broad range of acyl fluorides are accessible from carboxylic acids while avoiding the formation of acid anhydrides. ¹⁹F NMR spectra suggest that S₈-fluoro-sulfonium cation A and neutral S₈-difluoride A' generated in situ are the reactive species in this deoxyfluorination reaction.