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. 2025 Dec 5;27(48):13223-13228.
doi: 10.1021/acs.orglett.5c04085. Epub 2025 Nov 24.

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

Emma S Gogarnoiu  1 , Melissa S Griffin  1 , Ajay H Bansode  1 , Joshua M Paolillo  1 , Joseph M Bergen  1 , Marvin Parasram  1
Affiliations

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

Emma S Gogarnoiu et al. Org Lett. .

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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Figures

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1. Acyl Fluoride Synthesis and Alkenyl Fluoride Utility
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