Organoaluminum Compounds as Catalysts for Monohydroboration of Carbodiimides

The effective catalytic activity of organoaluminum compounds for the monohydroboration of carbodiimides has been demonstrated. Two aluminum complexes, 2 and 3, were synthesized and characterized. The efficient catalytic performances of four aluminum hydride complexes L1 AlH2 (L1 =HC(CMeNAr)2 , Ar=2,6-Et2 C6 H3 ; 1), L2 AlH2 (NMe3 ) (L2 =o-C6 H4 F(CH=N-Ar), Ar=2,6-Et2 C6 H3 ; 2), L3 AlH (L3 =2,6-bis(1-methylethyl)-N-(2-pyridinylmethylene)phenylamine; 3), and L4 AlH(NMe3 ) (L4 =o-C6 H4 (N-Dipp)(CH=N-Dipp), Dipp=2,6-iPr2 C6 H3 ; 4), and an aluminum alkyl complex L1 AlMe2 (5) were used for the monohydroboration of carbodiimides investigated under solvent-free and mild conditions. Compounds 1-3 and 5 can produce monohydroborated N-borylformamidine, whereas 4 can afford the C-borylformamidine product. A suggested mechanism of this reaction was explored, and the aluminum formamidinate compound 6 was characterized by single-crystal X-ray, also a stoichiometric reaction was investigated.