Practical and direct synthesis of α-aminonitriles using N-Boc-O-tosyl alkylhydroxylamines and TMSCN.

Herein, we report a practical and direct method for the synthesis of α-aminonitriles from easily accessible N-Boc-O-tosyl alkylhydroxylamines. The transformation proceeds under mild, transition-metal-free, and redox-neutral conditions using readily available reagents and is readily scalable to the gram scale. Mechanistic studies indicate that the reaction proceeds via in situ imine formation enabled by CsF, followed by nucleophilic cyanation. Furthermore, the synthetic utility of the products is demonstrated through diverse downstream transformations.