The first chapter of the thesis describes an iron(II)-catalyzed intermolecular amino-oxygenation of alkenes. This amino-oxygenation method is found to be compatible with a broad range of synthetically valuable alkenes and affords the corresponding 1,2-amino alcohols with excellent regio- and diastereoselectivity. Additionally, practical synthetic procedures for the amino-oxygenation of styrene, a fully functionalized glycal, and indene are described. The second chapter of the thesis describes a regioselective and diastereoselective iron(II)-catalyzed intermolecular aminofluorination of alkenes using nucleophilic fluorinating reagents. This method affords new vicinal amino fluorides that were previously difficult to prepare. In both the amino-oxygenation and aminofluorination reactions, bench-stable hydroxylamine derivatives functioned as both the oxidant and amination reagents. Preliminary mechanistic studies suggested that an iron-nitrenoid is a possible reactive intermediate on both reaction pathways. These new difunctionalization strategies represent efficient alternatives to current amino-oxygenation and aminofluorination methods.