The pyridylseleno group in organic synthesis. Part 5. Amidoseleniation of alkenes

Abstract

The reaction of β-methoxyalkyl 2-pyridyl selenides with acetonitrile in the presence of trifluoromethanesulphonic acid and water affords β-acetamidoalkyl 2-pyridyl selenides in good to excellent yields. This reaction has been used in the two-step amidoseleniation of electron-rich alkenes such as styrene and buta-1,3-dienes, and of tri- or tetra-substituted alkenes, previously reported as being resistant to amidoseleniation.