Visible-Light-Induced Desaturative β-Alkoxyoxalylation of N-Aryl Cyclic Amines with Difluoromethyl Bromides and H2O Via a Triple Cleavage Process

A visible-light-driven desaturative beta-alkoxyoxalyation of N-aryl cyclic amines with difluoromethyl bromides and H2O has been reported. This tandem reaction is triggered by homolysis of the C-Br bond to produce the difuoroalkyl radical, which undergoes the subsequent defluorinated beta-alkoxyoxalylation cascades to afford a wide range of beta-ketoester/ketoamides substituted enamines. The prominent feature of this reaction contains photocatalyst-free, transition-metal free, and mild conditions. The O-18 labeling experiment disclosed that H2O is the oxygen source of the carbonyl unit.

Automated summary

A visible-light-driven desaturative beta-alkoxyoxalyation reaction has been reported. The reaction proceeds under mild conditions and does not require a photocatalyst or transition metal. The C-Br bond undergoes homolysis to produce a difluoroalkyl radical, which then undergoes defluorinated beta-alkoxyoxalylation cascades to yield a wide range of beta-ketoester/ketoamide substituted enamines. The oxygen source for the carbonyl unit is confirmed to be H2O through O-18 labeling experiments.