Functionalized allylamines are useful synthetic targets and important intermediates in the synthesis of pharmaceuticals such as cinnarizine (for the treatment of vertigo), flunarizine (for chronic migraine relief) and naftifine (antifungal for athlete’s foot treatment). The traditional synthesis of these compounds is atom-inefficient and requires the use of protecting groups and purification steps, so new and “greener” methods are still sought after.
In this work, Joseph Schmidt and co-workers from the University of Toleda, USA, have reported the synthesis of several allylamine compounds using a 100% atom economic hydroamination route. Their palladium complex catalyst [(3IPtBu)Pd(allyl)]OTf could efficiently catalyse the reaction of allenes with alkyl amines at room temperature to produce the target compounds in good to excellent yields. Using p-fluorophenylallene as a starting material allowed for the selective isolation of either the branched or linear hydroamination product in high yield by adjusting the catalyst loading and reaction time.
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Palladium catalyzed intermolecular hydroamination of 1-substituted allenes: an atom-economical method for the synthesis of N-allylamines, John F. Beck, Danielle C. Samblanet and Joseph A. R. Schmidt, RSC Advances, 2013, DOI: 10.1039/c3ra43870h
