Synthesis of Nitriles from Primary Azides with Ru(OH)_x/Al₂O₃

Significance

Alumina-supported ruthenium hydroxide Ru(OH)_x/Al₂O₃ catalyzed the aerobic oxidative synthesis of nitriles 2 from primary azides 1 under atmospheric conditions. Benzylic as well as aliphatic primary azides 1 underwent the oxidative transformation with Ru(OH)_x/Al₂O₃ (4 mol% Ru) to give the corresponding nitriles 2 in up to 94% yield (13 examples). The catalyst was recovered by simple filtration and reused twice without significant loss of its catalytic activity in the formation of 2a (1^st reuse: 80% yield, 2^nd reuse: 81% yield).