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Updated: Jan 10, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Photoinduced Cleavage of Alkenyl Fluorides for Nucleophilic Acyl Substitution via In Situ Generated Acyl Fluorides
Emma S Gogarnoiu1, Melissa S Griffin1, Ajay H Bansode1
1Department of Chemistry, New York University, 24 Waverly Place, Third Floor, New York, New York 10003, United States.
Abstract:
Acyl fluorides are valuable intermediates due to their stability and unique reactivity with amines, enabling selective acyl substitution. We report a mild one-pot method to access amides, esters, and thioesters from alkenyl fluorides. Visible-light photoexcitation of 4-nitrophthalonitrile promotes cleavage of the alkenyl fluoride, forming acyl fluorides in situ for nucleophilic acyl substitution. This protocol offers broad utility as demonstrated in the synthesis of linear peptide fragments.
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