An experimentally convenient procedure for the generation of 4,5-dimagnesioimidazoles is described. N-Protected 2-substituted 4,5-diiodoimidazoles were treated with i-PrMgCl (2.4 equiv) in THF at 0-5 degrees C. The resulting vicinal dianions reacted with electrophiles to give 4,5-disubstituted imidazoles in 27-71% yields.
Synthesis and Chemistry of 4,5-Dimagnesioimidazole Dianions. -Treatment of 4,5-diiodoimidazoles like (I) and (IV) with 2.4 equiv. iPrMgCl results in facile formation of 4,5-dimagnesioimidazole dianions which can be trapped by different electrophiles to yield 4,5-disubstituted imidazoles such as (III) and (VI). -(BUTZ, RALF H.-J.; LINDELL, STEPHEN D.; J.
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