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

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.