Abstract:

Metal hydride hydrogen atom transfer (HAT) has emerged as a highly chemoselective method for the hydrofunctionalization of alkenes. This methodology has enabled practitioners to incorporate a wide range of functional groups into complex molecules. Despite the significant advances in the selectivity of the HAT event, there are still limitations. To bridge these gaps in methodology, my work focused on the development of iron hydride HAT reactions utilizing alcohols and amines as directing groups. I demonstrated that modification of conventional reaction conditions allows the directing effect of alcohols and amines to be realized in iron-catalyzed HAT reactions. These methods enable the site selective hydrofunctionalization of polyenols and polyenamines. Furthermore, the amine-directed method enables hydrofunctionalization of cis, trans, and tetrasubstituted alkenes with predictable regiochemical outcomes.