Synthesis of Aryl Amine Derivatives from Benzyl Nitriles via Electrocyclization of in Situ Generated <i>N</i>‑Silyl Ketene Imines

The previously unexplored reactivity of <i>N</i>-silyl ketene imines in organic synthesis is reported. Benzyl nitriles containing an alkenyl or aryl group at the <i>ortho</i> position were smoothly converted into aryl amines in good yields under two sets of mild silylation conditions: (1) nonbasic conditions using TMSNTf₂–<i>i</i>Pr₂NEt or (2) basic anionic conditions using lithium diisopropylamide–triisopropylsilyl chloride (LDA–TIPSCl). The reaction probably proceeds via in situ generation of an <i>N</i>-silyl ketene imine followed by 6π-electrocyclization and aromatization