Amidoselenation of olefins via hydroxyselenation: reactions using nitriles in reagent quantity and the synthesis of β-(acrylamido)alkyl phenyl selenides

Abstract

Limitations in a previously reported amidoselenation reaction have been overcome by the use of β-hydroxyalkyl phenyl selenides, (1) and (2), as starting materials; these when treated with nitriles (1–5 equiv.) in dichloromethane in the presence of trifluoromethanesulphonic acid afforded the β-amidoalkyl phenyl selenides (3) or (4) in good yield. Further, side reaction brought about by hydrogen chloride have been prevented; thus (1) and (2) in the presence of acid afforded the β-(acrylamido)alkyl phenyl selenides (5) or (7), free from side products.