Litcius/Paper detail

Site-Selective, Photocatalytic Vinylogous Amidation of Enones

Kitti Franciska Szabó, Katarzyna Goliszewska, Jakub Szurmak, Katarzyna Rybicka‐Jasińska, Dorota Gryko

2022Organic Letters21 citationsDOIOpen Access PDF

Abstract

High Resolution Image Download MS PowerPoint Slide Despite the broad interest in organic compounds possessing a γ-aminocarbonyl motif, limited strategies for their synthesis have been reported. Herein, we describe a mild and efficient method for the site-selective amidation of unsaturated enones with electrophilic N-centered radicals as a key intermediate. The photocatalytic vinylogous reaction of dienolates with N -amino pyridinium salts affords γ-amido carbonyl compounds. This process is high-yielding, scalable, and tolerates a broad range of unsaturated α,β-unsaturated carbonyls, including biologically relevant compounds, as starting materials.

Topics & Concepts

ChemistryPyridiniumElectrophilePhotocatalysisRadicalOrganic chemistryCombinatorial chemistryCatalysisCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques