Transformation of Aliphatic and Aromatic Secondary Amides to Nitriles

Huang et al. have reported the transformation of aliphatic and aromatic secondary amides to nitriles. According to their results, by using trifluoromethanesulfonic anhydride in combination with 2-fluoropyridine, secondary amides are successfully transformed into the corresponding nitriles with the elimination of an N-alkyl group under mild reaction conditions. This reaction effectively proceeds when using amides bearing either secondary, tertiary, or benzylic N-alkyl groups. In addition, the reaction also tolerates several labile functional groups such as esters, ketones and aldehydes. Thus this synthetic approach has attracted much attention as a useful synthetic method for nitriles.