DecaboraneDecaborane (B10H14) is a stable, crystalline borane. It is neither air nor hydrolysis-sensitive. Even melting and boiling points of the substance could be determined: 100°C, 213°C.
Decaborane was already used early as reducing agent, but its reduction strength was modest. Only the replacement of polar by protic solvents or the addition of additives permits the employment of decaborane as a mild reducing agent in the reductive etherification and amination as well as in the reduction of nitro groups.
Aromatic aldehydes were easily converted to the corresponding ethers in methanol or ethanol using decaborane at r.t. under nitrogen in high yields.
S. H. Lee, Y. J. Park, C. M. Yoon, Tetrahedron Lett., 1999, 40, 6049-6050.
Aldehydes and ketones were easily converted to the corresponding amines by the reaction of amines in methanol using decaborane (B10H14) at room temperature under nitrogen. The reaction is simple and efficient.
J. W. Bae, S. H. Lee, Y. J. Cho, C. M. Yoon, J. Chem. Soc., Perkin Trans. 1, 2000, 145-146.
Decaborane was found to be an effective agent for the chemoselective reduction of ketones to alcohols in the presence of pyrrolidine and cerium(III) chloride heptahydrate in methanol.
J. W. Bae, S. H. Lee, Y. J. Jung, C.-O. Maing, C. M. Yoon, Tetrahedron Lett., 2001, 42, 2137-2139.
N-Alkylaminobenzenes were prepared in a simple and efficient one-pot synthesis by reduction of nitrobenzenes followed by reductive amination with decaborane (B10H14) in the presence of 10% Pd/C.
J. W. Bae, Y. J. Cho, S. H. Lee, C.-O. M. Yoon, C. M. Yoon, Chem. Commun., 2000, 1857-1858.