A facile synthesis of primary amines via organoboranes

Primary amines are formed via the reaction of organoboranes with hydrazoic acid. Reactions have been carried out using both preformed hydrazoic acid and in situ generated hydrazoic acid. A series of representative alkenes were hydroborated and used to form primary amines via hydrazoic acid.

Trimethylsilyl azide was also used to synthesize primary amines via reaction with organoboranes. The reactions were carried out with both commercially available trimethylsilyl azide and in situ generated azide. A series of alkenes were hydroborated and used to form primary amines via trimethylsilyl azide.