Deoxygenation of Primary Amides to Amines with Pinacolborane Catalyzed by Ca[N(SiMe3)2]2(THF)2

Deoxygenative reduction of amides is a challenging but favorable synthetic method of accessing amines. In the presence of a catalytic amount of Ca[N(SiMe3)(2)](2)(THF)(2), pinacolborane (HBpin) could efficiently reduce a broad scope of amides, primary amides in particular, into corresponding amines. Functional groups and heteroatoms showed good tolerance in this process of transformation, and a plausible reaction mechanism was proposed.

Automated summary

The deoxygenative reduction of amides using pinacolborane (HBpin) in the presence of a catalytic amount of Ca[N(SiMe3)(2)](2)(THF)(2) is an efficient method to access amines, with good tolerance to functional groups and heteroatoms. The proposed reaction mechanism provides insight into this transformation.