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The first spontaneous, metal-free, room-temperature hydrogen transfer from ammonia borane to an iminoborane is reported. Mechanistic studies of the reaction indicate a concerted transfer of H + and H - from donor to acceptor with an activation energy far below those of comparable concerted transfer hydrogenations. This reaction was employed in the syntheses and isolation of new B,N-disubstituted aminoboranes, a comparatively rare subset within the aminoborane family. This successful transfer hydrogenation to a highly dehydrogenated BN system may serve as a starting point for the design of new systems capable of reversible dehydrogenation/rehydrogenation., (© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)