Selectivity matters: Graphene oxide-mediated oxidative coupling of benzylamine to N‑benzylidine-1-phenylmethanamine under microwave irradiation

• Selective and efficient oxidative coupling of benzylamine.
• Reaction catalysed by graphene oxide in the absence of oxidant.
• Favoured formation of an imine intermediate on graphene oxide.
• A plausible reaction mechanism is proposed.

A selective, efficient and benign oxidative coupling of benzylamine under microwave irradiation was achieved at mild reaction conditions in the absence of oxidant using graphene oxide as catalyst. Reaction conditions seem to point to the favoured formation of an imine intermediate which subsequently reacts with benzylamine to provide high selectivities at almost quantitative conversion of starting material to the oxidative coupling product N‑benzylidine-1-phenylmethanamine. A plausible reaction mechanism is proposed.

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