Iron-catalyzed hydrosilylation of diacids in the presence of amines: a new route to cyclic amines

Cyclic amines (such as pyrrolidines, piperidines and azepanes) are present in a large class of natural products and bioactive molecules. Herein, we present a novel chemoselective strategy for building N-substituted cyclic amines via iron catalyzed one-pot hydrosilylation starting from readily available dicarboxylic acids and amines, with hydrosilanes as the hydride sources. The described methodology allows the preparation of a wide range of N-alkylated and arylated cyclic amine derivatives (including pharmaceuticals Fenpiprane and Prozapine) in moderate to excellent yields, starting from inexpensive succinic, glutaric, and adipic acids with dimethyl carbonate as a green solvent.