Journal of Organic Chemistry p. 4727 - 4733 (1981)
Update date:2022-08-04
Topics:
Toshimitsu, Akio
Aoai, Toshiaki
Owada, Hiroto
Uemura, Sakae
Okano, Masaya
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.
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