Joanna Teresa Negri

The use of borane–amine adducts as versatile palladium-catalyzed hydrogen-transfer reagents in methanol

Abstract The scope of borane–amine adducts as reducing agents is broadened through palladium-catalyzed methanolysis capable of reducing a wide variety of functional groups. Hence, borane mediated reduction of a benzamide followed by a tandem methanolysis/hydrogenolysis of the resulting borane–benzylamine adduct allows chemoselective removal of an N -benzoyl in the presence of an O -benzoyl.

Palladium catalyzed activation of borane–amine adducts: rate enhancement of amine–borane methanolysis in the reduction of nitrobenzenes to anilines

Abstract Hydrolytically stable borane–amines can be activated in situ through palladium catalysis and perform reductions not possible otherwise. Hence, borane–trimethylamine is an efficient hydrogen-transfer reagent for the open vessel reduction of nitroaryls to anilines. Likewise, the palladium catalyzed methanolysis/decomplexation of stable borane–amine adducts is accelerated by the action of nitrobenzene.