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Transfer hydrogenation of imines with ammonia-borane: a concerted double-hydrogen-transfer reaction.

Ammonia–borane (H3N-BH3, AB) is considered a feasible material for chemical hydrogen storage owing to its ideally very high storage capacity (19.6 weight% H) and thus has attracted much attention. Dehydrogenations of AB were accomplished either thermally or by transition metal catalysis. Considering AB as a significantly polarized molecule, we reasoned that it could be dehydrogenated by direct reaction with a similarly polarized unsaturated compound by the rarely explored reaction mode of double H transfer (Scheme 1).