Journal article
Chemoselective Alkylations with N- and C-Metalated Nitriles
Organic letters, v 17(19), pp 4906-4909
02 Oct 2015
PMID: 26390098
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
Metalated nitriles exhibit complementary chemoselectivities in electrophilic alkylations. N-Lithiated or C-magnesiated nitriles can be prepared from the same nitrile precursor and selectively reacted with a 1:1 mixture of methyl cyanoformate and benzyl bromide or bifunctional electrophiles through chemoselective attack onto either an alkyl halide or a carbonyl electrophile. A mechanistic explanation for the chemoselectivity preferences is provided that rests on the structural and complexation differences between N- and C-metalated nitriles.
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Details
- Title
- Chemoselective Alkylations with N- and C-Metalated Nitriles
- Creators
- Xun Yang - Duquesne UniversityDinesh Nath - Duquesne UniversityFraser F. Fleming - Duquesne University
- Publication Details
- Organic letters, v 17(19), pp 4906-4909
- Publisher
- American Chemical Society; Washington, DC
- Number of pages
- 4
- Grant note
- National Science Foundation (IRD) 1639875 / Direct For Mathematical & Physical Scien; National Science Foundation (NSF); NSF - Directorate for Mathematical & Physical Sciences (MPS) CHE 1111406 / National Science Foundation; National Science Foundation (NSF)
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000362384700065
- Scopus ID
- 2-s2.0-84942895445
- Other Identifier
- 991019169907604721
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- Collaboration types
- Domestic collaboration
- Web of Science research areas
- Chemistry, Organic