Palladium-catalyzed diastereoselective cross-coupling of two aryl halides <i>via</i> C–H activation: synthesis of chiral eight-membered nitrogen heterocycles

Abstract

A method for the synthesis of enantiopure eight-membered nitrogen heterocycles has been developed through diastereoselective cross-coupling of 2-iodobiphenyls with 2-bromobenzylamines. The products represent a novel type of chiral scaffold, which feature easy modification and high configurative stability and have the potential to be applied in asymmetric synthesis. Palladacycles that were formed via the C-H activation of 2-iodobiphenyls should act as the intermediates. The reaction provides a new strategy for the synthesis of medium-sized ring compounds.