Site-Selective, Photocatalytic Vinylogous Amidation of Enones

Despite the broad interest in organic compounds possessing a gamma-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 gamma-amido carbonyl compounds. This process is high-yielding, scalable, and tolerates a broad range of unsaturated alpha,beta-unsaturated carbonyls, including biologically relevant compounds, as starting materials.

Automated summary

In this study, a mild and efficient method for the synthesis of organic compounds with a gamma-aminocarbonyl motif was described. The photocatalytic vinylogous reaction of dienolates with N-amino pyridinium salts resulted in high-yielding and scalable gamma-amido carbonyl compounds.