Amidophosphine Boranes as Hydroboration Reagents for Nitriles, Alkynes, and Carboxylic Acids.

Abstract

We report here the hydroboration of nitriles, alkynes, and carboxylic acids using amidophosphine boranes {(BH3)(PPh2)-NC(CH3)3}, {(BH3)2(PPh)2N(CH2)C6H5}, and {(BH3)2(PPh2)2N-(BH3)CH2C6H4N} as reducing agents. These compounds were synthesized to replace more commonly used borane reagents. Solid amidophosphine boranes, which were synthesized with ease, demonstrated excellent reactivity and functional group tolerance toward a wide variety of nitriles, alkynes, and carboxylic acids, affording the corresponding ammonium salts, alkenes, and alcohols in good yield.