Journal article
Metalated nitriles: organolithium, -magnesium, and -copper exchange of alpha-halonitriles
Journal of organic chemistry, v 70(6), pp 2200-2205
18 Mar 2005
PMID: 15760206
Featured in Collection : UN Sustainable Development Goals @ Drexel
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.
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Details
- Title
- Metalated nitriles: organolithium, -magnesium, and -copper exchange of alpha-halonitriles
- Creators
- Fraser F Fleming - Duquesne UniversityZhiyu ZhangWang Liu - Duquesne UniversityPaul Knochel - Duquesne University
- Publication Details
- Journal of organic chemistry, v 70(6), pp 2200-2205
- Publisher
- American Chemical Society; Washington, DC
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000227566400033
- Scopus ID
- 2-s2.0-15444369069
- Other Identifier
- 991020898393104721
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- Collaboration types
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Chemistry, Organic