Palladium-Catalyzed Site-Selective Hydrogenation of Unactivated Alkenes Directed by 8-Aminoquinoline Amides

Abstract

We have developed a method for the site-selective hydrogenation of unactivated alkenes using 8-aminoquinoline amide as the directing group. For unactivated alkenes with two C–C double bonds, Daugulis’s 8-aminoquinoline amide facilitated the site-selective hydrogenation of the desired C–C double bond, producing a product in which one C–C double bond was reduced. Site-selective reduction methodologies using intramolecular directing groups are expected to contribute significantly to the synthesis of molecules with multiple reducible functional groups in the future.