GENERATION AND TRAPPING OF FUNCTIONALIZED ARYL- AND HETEROARYLMAGNESIUM AND -ZINC COMPOUNDS

摘要

Zinc and magnesium organometallic reagents are intimately linked with the development of synthetic organic chemistry. Grignard reported the well-known magnesium insertion into organic halides for preparing organomagnesium halides in ether and their further reactions with organic electrophiles. The higher polarity of the carbon-magnesium bond compared to the carbon-zinc bond and consequent higher reactivity of the organomagnesium reagents compared to the organozinc reagents leads generally to higher yields in reactions with electrophilic reagents, explaining the broad applications of Grignard reagents in comparison to organozinc compounds. Thus, with the exception of zinc enolates, introduced by Reformatsky,12 and the Simmons-Smith reagent, ICH2ZnI, organomagnesium reagents rapidly replaced organozinc reagents in organic synthesis.