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

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 S...

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Bibliographic Details
Published inOrganic letters Vol. 25; no. 16; pp. 2810 - 2814
Main Authors Mahmoud, Elsayed M., Mori, Soichiro, Sumii, Yuji, Shibata, Norio
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 28.04.2023
Amer Chemical Soc
Subjects
anhydrides
cations
Chemistry
Chemistry, Organic
Lewis acids
Physical Sciences
Science & Technology
DEOXYFLUORINATION
SALTS
GENERATION
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ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/acs.orglett.3c00701

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Summary: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.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.3c00701