Directed C(sp3)−H vinylation and arylation of alkylimines for the synthesis of branched allylamines and azaarylmethylamines

Abstract

We report herein a transition-metal-free C(sp3)–C(sp2) cross-coupling approach to prepare branched allylamines and azaarylmethylamines. The key to the process is the enhanced reactivity of the 2-azaallyl anions generated from N-fluorenyl alkylimines. A broad range of functional groups and proceeds under room temperature without transition metals, external initiators or photoredox catalysts. Notably, no deprotonative isomerization or C3 site-selectivity products was observed. The synthetic utility of the present work was showcased by an efficient one-pot procedure and ketoimine hydrolysis.