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. Key to the process is the enhanced reactivity of the 2-azaallyl anions generated from N-fluorenyl alkylimines. A broad range of functional groups are tolerated and the reaction proceeds under room temperature conditions without transition metals, external initiators or photoredox catalysts. Notably, no deprotonative isomerization or C₃ site-selective products were observed. The synthetic utility of the present work was showcased by an efficient one-pot procedure and ketoimine hydrolysis.