Amidoselenation of Olefins and Its Utilization for Synthesis of Allylic Amides

Article abstract of DOI:10.1021/jo00336a021

The reaction of phenylselenyl chloride with olefins in acetonitrile containing trifluoromethanesulfonic acid and water affords β-acetamidoalkyl phenyl selenides in good to excellent yields.This represents the first example of one-pot amidoselenation of mono- and disubstituted olefins.The reaction can be carried out in benzonitrile, propionitrile, butyronitrile, or ethyl cyanoacetate.It was confirmed that the amidoselenation reaction proceeds with trans stereospecifity.Oxidative elimination of the produced β-amidoalkyl phenyl selenides gives allylic amides selectively in good to excellent yields.These two reactions constitute a good method for conversion of olefins to allylic amides.