Regioselective magnesiation of N-heterocyclic molecules: securing insecure cyclic anions by a ß-diketiminate-magnesium clamp.

ABSTRACT

Using a specially designed magnesium metallating manifold, combining kinetically activated TMP amide base with a sterically amplified ß-diketiminate ligand, this study has established a new regioselective strategy for magnesiation of challenging N-heterocyclic molecules. The broad scope of the approach is illustrated through reactions of pyrazine, triazoles and substituted pyridines by isolation and structural elucidation of their magnesiated intermediates.