Photoinduced Cleavage of Alkenyl Fluorides for Nucleophilic Acyl Substitution via In Situ Generated Acyl Fluorides

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.