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: flemingf
duq.edu
F. F. Fleming, Z. Zhang, W. Liu, P. Knochel, J. Org. Chem., 2005, 70, 2200-2005.
DOI: 10.1021/jo047877r
Abstract
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.
see article for more examples
see article for more reactions
Key Words
Nitriles, Grignard reagents, Carboxylations, Allylations, Ketones, Alcohols
ID: J42-Y2005-300
