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

Davin, Laia and McLellan, Ross and Hernán-Gómez, Alberto and Clegg, Bill and Kennedy, A R and Stepek, Iain and Mertens, Maria and Hevia, Eva (2017) Regioselective magnesiation of N-heterocyclic molecules: securing insecure cyclic anions by a β-diketiminate-magnesium clamp. Chemical Communications. ISSN 1359-7345

[img]
Preview
Text (Davin-etal-CC2017-regioselective-magnesiation-of-N-heterocyclic-molecules)
Davin_etal_CC2017_regioselective_magnesiation_of_N_heterocyclic_molecules.pdf
Accepted Author Manuscript

Download (899kB)| Preview

    Abstract

    Using a specially designed magnesium metallating manifold, combining kinetically activated TMP amide base with a sterically amplified β-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 through isolation and structural elucidation of their magnesiated intermediates.