83475-26-7Relevant articles and documents
Metal-free dehydrogenation of amine-boranes by an N-heterocyclic carbene
Sabourin, Kyle J.,Malcolm, Adam C.,McDonald, Robert,Ferguson, Michael J.,Rivard, Eric
, p. 4625 - 4632 (2013)
The dehydrogenation of primary and secondary amine-boranes (RNH 2·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 IPrH 2 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*NH 2·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. The Royal Society of Chemistry 2013.