Rh(i)-catalysed imine-directed C–H functionalization via the oxidative [3 + 2] cycloaddition of benzylamine derivatives with maleimides

Abstract

The Rh(I)-catalysed imine-directed oxidative [3 + 2] cycloaddition of benzylamines with maleimides is reported. A wide range of both benzylamines and maleimides is applicable to the reaction. A one-pot three component strategy using benzylamines, 2-pyridinecarboxaldehyde, and maleimides is successfully achieved. Mechanistic studies including deuterium labelling experiments suggest that a zwitterionic intermediate is formed and is a key intermediate through the Rh-catalysed activation of a benzylic C(sp³)–H bond of the imine.