Synthesis of Dibenzo[b,f]azepines via Palladium-Catalyzed Cascade [4+3] Annulation of o-Alkenyl Bromoarenes and o-Bromoaniline Derivatives

A cascade [4+3] annulation of o-alkenyl bromoarenes and o-bromoaniline derivatives was described. Various dibenzo[b,f]azepines with substitutions on the 10/11 position were obtained in 14-97% yields. The synthetic versatility of this protocol is highlighted by the preparation of a precursor of the drug molecule oxcarbazepine, a gram-scale synthesis, and two product transformations. Unlike previous amination/Heck sequence, this cascade process is supposed to undergo a C(vinyl), C(aryl)-palladacycle involved pathway.

Automated summary

A cascade [4+3] annulation of o-alkenyl bromoarenes and o-bromoaniline derivatives is reported, leading to the synthesis of various dibenzo[b,f]azepines with substitutions on the 10/11 position in moderate to high yields. The versatility of this protocol is demonstrated through the preparation of a precursor for the drug molecule oxcarbazepine, gram-scale synthesis, and two product transformations. Unlike previous amination/Heck sequences, this cascade process follows a C(vinyl), C(aryl)-palladacycle involved pathway.