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The dehydrogenation of primary and secondary amine–boranes (RNH2·BH3 and R2NH·BH3; R = alkyl groups) was studied using the bulky N-heterocyclic carbene IPr (IPr = [(HCNDipp)C:]; Dipp = 2,6-iPr2C6H3) as a stoichiometric dehydrogenation agent. In the case of primary amine–boranes, carbene-bound adducts IPr·BH2–NH(R)–BH3 were obtained in place of the desired polymers [RNH–BH2]n. The secondary amine–borane iPr2NH·BH3 participated in dehydrogenation chemistry with IPr to afford the aminoborane [iPr2NBH2] and the dihydroaminal IPrH2 as products. Attempts to induce H2 elimination from the arylamine–borane DippNH2·BH3 yielded a reaction mixture containing the known species IPr·BH2NHDipp, IPr·BH2NH(Dipp)–BH3, free DippNH2 and IPrH2. The new hindered aryl-amine borane adduct Ar*NH2·BH3 [Ar* = 2,6-(Ph2CH)2-4-MeC6H2] underwent a reaction with IPr to give IPr·BH3 and free Ar*NH2, consistent with the presence of a weaker N–B dative bond in Ar*NH2·BH3 relative to its less hindered amine–borane analogues.
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