Comparing References
Tatarinov, D. A.; Mironov, V. F.; Varaksina, E. N.; Krivolapov, D. B.; Litvinov, I. A.; Musin, R. Z.; Buzykin, B. I.; Konovalov, A. I. Mendeleev Commun. 2008, 18, 147-149.
Dobrovolná, Z.; Červený, L. Res. Chem. Intermed. 2000, 26, 489-497.
Seyferth, D. Organometallics 2009, 28, 1598-1605.
Grignard reagents, such as vinyl magnesium bromide, are easily prepared and quite reactive, making them ideal for synthetic chemistry. Most often they are prepared in an ethereal solution (diethyl ether or THF) by the reaction of an organic halide with metallic magnesium. Dietmar Seyferth (2009) notes that in most cases, Grignard reagents act as nucleophiles due to the polarity of the carbon-magnesium bond. In the presence of a palladium catalyst, vinylic Grignard reagents can displace halides to form new carbon-carbon bonds (Figure 3). This reaction is considered one of the most versatile procedures for the cross-coupling of Grignard reagents with organic halides. When vinyl magnesium bromide reacts with lactol 23 in THF, the nucleophilic alkene bonds with carbon. Although a Pd catalyst is not used with vinyl magnesium bromide, this reaction resembles the one described by Seyferth, as displayed in Figure 3. However, this example represents only a small fraction of potential Grignard reagents-based reactions.
Citing References
Köhler, M.; Langer, J.; Görls, H.; Westerhausen, M. Organometallics 2012, 31, 8647-8653.
These researchers used the knowledge that Grignard reagents are widely used in synthetic organic chemistry to synthesize meta-substituted arylcalcium iodides.
Magrez, M.; Guen, Y. L.; Baslé, O.; Crévisy, C.; Mauduit, M. Chem. Eur. J. 2013, 19, 1199-1203.
These researchers used the knowledge that Grignard reagents can form new carbon-carbon bonds when paired with transition metal catalysts to perform the copper-catalyzed asymmetric substitution of allyl phosphates.
Wu, J. C.; Gong, L. B.; Xia, Y.; Song, R. J.; Xie, Y. X.; Li, J. H. Angew. Chem. Int. Ed. 2012, 51, 9909-9913.
These researchers cited that cross-coupling an organic electrophile with a Grignard reagent produces a new carbon-carbon bond in order to synthesize alkenes and arylketones using the nickel-catalyzed Kumada reaction.
