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Metalated Nitriles: Organolithium, -magnesium, and -copper Exchange of α-Halonitriles

Fraser F. Fleming,* Zhiyu Zhang, Wang Liu and Paul Knochel

*Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, Pennsylvania 15282-1530, Email:

F. F. Fleming, Z. Zhang, W. Liu, P. Knochel, J. Org. Chem., 2005, 70, 2200-2005.

DOI: 10.1021/jo047877r


α-Halonitriles react with alkyllithium, organomagnesium, and lithium dimethylcuprate reagents generating reactive, metalated nitriles. The rapid halogen-metal exchange with alkyllithium and Grignard reagents allows Barbier-type reactions with various electrophiles.

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Key Words

Nitriles, Grignard reagents, Carboxylations, Allylations, Ketones, Alcohols

ID: J42-Y2005-300