Research in our group has recently focused on the use of N-heterocyclic carbenes as ligands for the iron-catalyzed cross-coupling of non-activated aryl chlorides with primary and secondary alkyl Grignard reagents.  Even though it is well known that Grignard reagents exist as an equilibrium mixture of alkylmagnesium halide and dialkylmagnesium species, there has been no study reported that determines which of these species is/are responsible for the cross-couplings observed in iron-catalyzed systems.  An understanding of which species is/are responsible for such cross-coupling reactions would allow for the optimization of reaction conditions.  We report on the studies performed aimed at exposing whether the alkylmagnesium halide, the dialkylmagnesium, or both species are responsible for observed cross-coupling behavior.

Schlenk equilibrium effects on iron-catalyzed cross-coupling reactions of aryl chlorides with alkyl Grignard reagents

243rd National Meeting (2012)

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