Journal article
Cyclic Alkenenitriles: Copper-Catalyzed Deconjugative alpha-Alkylation
Journal of organic chemistry, v 81(10), pp 4098-4102
20 May 2016
PMID: 27171565
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
An amido cuprate formed from CuCN and LDA allows a general deconjugative a-alkylation of cyclic alkenenitriles. Deprotonating cyclic alkenenitriles with LDA-CuCN avoids polymerization that otherwise plagues these alkylations and generates a reactive metalated nitrile for alkylations with a range of carbon and heteroatom electrophiles. The strategy provides an effective synthesis of quaternary 5-, 6-, and 7-membered cycloalk-1-enecarbonitriles substituted on the nitrile-bearing carbon.
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Details
- Title
- Cyclic Alkenenitriles: Copper-Catalyzed Deconjugative alpha-Alkylation
- Creators
- Xun Yang - Duquesne UniversityDinesh Nath - University of OklahomaJared Morse - University of North Carolina at CharlotteCraig Ogle - University of North Carolina at CharlotteEmine Yurtoglu - Atatürk UniversityRamazan Altundas - Atatürk UniversityFraser Fleming - Drexel University
- Publication Details
- Journal of organic chemistry, v 81(10), pp 4098-4102
- Publisher
- American Chemical Society; Washington, DC
- Number of pages
- 5
- Grant note
- CHE 1464494 / National Science Foundation; National Science Foundation (NSF)
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000376476400013
- Scopus ID
- 2-s2.0-84971267977
- Other Identifier
- 991019168626804721
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- Collaboration types
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Chemistry, Organic