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Grignard Reagents and Iron

Iron exhibits a decisive advantage over most of the other metals: it is truly inexpensive and environmentally benign. Therefore, synthetic methods involving iron salts in organic chemistry have much expanded over the last decades, especially in coupling reactions. In 1972, Kumada and Corriu independently reported the crosscoupling reaction between Grignard reagents and organic halides catalyzed by nickel salts, later extended to palladium complexes. However, one year before, Tamura and Kochi already reported some successful examples of formal nucleophilic substitution between alkyl magnesium bromides and vinyl bromides in presence of a catalytic amount of FeCl3 in THF (Figure 1, eq 1) [1, 2]. Moreover, they early demonstrated the stereoselectivity of the coupling (Figure 1, eq 2).