A flurry of recent studies have revealed that group 2 organometallic reagents bearing bulky �-diketiminate ligands can effectively participate in the stabilisation of low oxidation state Mg(I) intermediates and trap highly reactive MgH2 clusters. Despite the increasing interest in the applications of this important family of compounds, their potential use as metallating reagents capable to promote direct Mg-H exchange reactions of organic molecules has not yet been investigated.In this talk, we will present our findings in developing novel alkyl and amido reagents supported by �-diketiminate ligands and assessing their metallating power towards promoting direct magnesiations of N-heterocyclic molecules such as 1,3-benzo(azoles). Reactivity studies employing benzothiazole disclose a new transition-metal free method to prepare homocoupled azoles, which involves the initial magnesiation of the heterocycle followed by a cascade of C-C coupling and ring opening reactions with a final hydrolysis/ oxidation step.

Chemical consequences of the direct magnesiation of N-heterocyclic molecules using β-diketiminate stabilised magnesium bases

245th National Meeting (2013)

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