Novel borane–selenium complex: highly selective reduction of tertiary amides and nitriles to the corresponding amines with sodium borohydride–dialkylselenium dibromide

The reaction of sodium borohydride with bis(2-bromoethyl)selenium dibromide and/or diethylselenium dibromide in tetrahydrofuran (THF) gave borane. Treatment of tertiary amides with mixtures of sodium borohydride and either of the dibromides in THF gave the corresponding amines. Similar reactions with secondary and primary amides did not proceed. Furthermore, under similar reduction conditions, the reaction of nitriles with the above reagents also gave the corresponding primary amines.

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