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Cleavage of Borane-Amine Adducts

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Palladium and Raney nickel catalyze the methanolysis of strongly complexed borane-amine adducts. The method is applicable to primary, secondary, tertiary, and aromatic amines, and the mildness of the reaction conditions allows preservation of otherwise labile functional groups.
M. Couturier, J. L. Tucker, B. M. Andresen, P. Dube, J. T. Negri, Org. Lett., 2001, 3, 465-467.

A selective mono-N-alkylation of 3-amino alcohols relies on formation of a stable chelate with 9-BBN. Three prototypical amino alcohols featuring various bridging units led selectively to the monoalkylated derivatives in very high yields.
G. Bar-Haim, M. Kol, Org. Lett., 2004, 6, 3549-3551.