title: Synthesis of Aryl Amine Derivatives from Benzyl Nitriles via Electrocyclization of in Situ Generated N-Silyl Ketene Imines.
abstract: The previously unexplored reactivity of N-silyl ketene imines in organic synthesis is reported. Benzyl nitriles containing an alkenyl or aryl group at the ortho position were smoothly converted into aryl amines in good yields under two sets of mild silylation conditions: (1) nonbasic conditions using TMSNTf2-iPr2NEt or (2) basic anionic conditions using lithium diisopropylamide-triisopropylsilyl chloride (LDA-TIPSCl). The reaction probably proceeds via in situ generation of an N-silyl ketene imine followed by 6π-electrocyclization and aromatization.
authors.affiliation: Department of Chemistry, Faculty of Science, Hokkaido University , Sapporo 060-0810, Japan.
authors.forename: Fumihiko
authors.initials: F
authors.lastname: Yoshimura
authors.affiliation: Graduate School of Chemical Sciences and Engineering, Hokkaido University , Sapporo 060-0810, Japan.
authors.forename: Taiki
authors.initials: T
authors.lastname: Abe
authors.affiliation: Department of Chemistry, Faculty of Science, Hokkaido University , Sapporo 060-0810, Japan.
authors.forename: Keiji
authors.initials: K
authors.lastname: Tanino