A sequential olefin hydroboration/Suzuki coupling for denitrogenative alkylation of benzotriazinones with α-olefins

A denitrogenative alkylation of N-aryl benzotriazinones using readily available α-olefins as alkyl sources via a hydroboration/palladium-catalyzed alkyl Suzuki coupling sequence is reported to afford ortho n-alkyl benzamides in good to excellent yields. Scope and limitations of the sequential hydroboration/Suzuki coupling protocol have been explored, showing large steric effects of both benzotriazinone core and alkylboranes. Only primary alkyl group of trialkylboranes from anti-Markovnikov hydroboration of α-olefins could be effectively coupled, making the protocol highly selective for ortho n-alkyl benzamides.