Metalated nitriles: organolithium, -magnesium, and -copper exchange of alpha-halonitriles |
| |
Authors: | Fleming Fraser F Zhang Zhiyu Liu Wang Knochel Paul |
| |
Institution: | Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, Pennsylvania 15282-1530, USA. flemingf@duq.edu |
| |
Abstract: | reaction: see text] alpha-Halonitriles react with alkyllithium, organomagnesium, and lithium dimethylcuprate reagents generating reactive, metalated nitriles. The rapid halogen-metal exchange with alkyllithium and Grignard reagents allows selective exchange in the presence of reactive carbonyl electrophiles, including aldehydes, providing a high-yielding alkylation protocol. Lithiated and magnesiated nitriles react with propargyl bromide by S(N)2 displacement whereas organocopper nitriles react by S(N)2' displacement, correlating with the formation of a C-metalated nitrile. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|