Selective Access of Deuterated Dibenzo-fused ε-Lactones and ε-Lactams via Palladium Carbene Migratory Insertion Enabled 1,4-Pd Shift

Since deuterated compounds have significant applications in pharmaceutical chemistry, selective incorporation of deuterium atoms onto a pharmacophore containing compounds has attracted great attention. Herein, we describe a concise method for construction of deuterated dibenzo-fused epsilon-lactones and epsilon-lactams via Pd-catalyzed carbene bridging C-D bond activation strategy. Readily available deuterated ortho-bromobenzaldehydes were employed as reactants, and deuterium atom was selectively incorporated at the dibenylic position with high deuterated ratio.

Automated summary

Deuterated compounds are important in pharmaceutical chemistry and the selective incorporation of deuterium atoms onto pharmacophore-containing compounds is of great interest. In this study, a concise method for constructing deuterated dibenzo-fused epsilon-lactones and epsilon-lactams through Pd-catalyzed carbene bridging C-D bond activation strategy was described. Deuterated ortho-bromobenzaldehydes were readily available reactants and deuterium atoms were selectively incorporated at the dibenylic position with high deuterated ratio.