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NMR kinetic studies on the decomposition of β-amidozinc reagents: Optimization of palladium-catalyzed cross-coupling with acid chlorides

Lookup NU author(s): Christopher Hunter, Professor Richard Jackson

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Abstract

The decomposition of β-amidozinc reagent 4 by β-elimination has been shown to be a unimolecular process in both THF and DMF as solvent, with relative rates of 4:1 at room temperature, and activation parameters have been determined. These results indicate the β-elimination is a syn-process. NMR experiments reveal that as little as 2 equiv of DMF can have a significant stabilizing influence on reagent 4. Use of a mixture of DMA and toluene as the bulk solvent, in place of DMF, has allowed successful palladium-catalyzed cross-coupling reactions of both 4 and the homologous reagent 5 with acid chlorides to yield unsymmetrical ketones (nine examples).


Publication metadata

Author(s): Dexter CS, Hunter C, Jackson RFW, Elliott J

Publication type: Article

Publication status: Published

Journal: Journal of Organic Chemistry

Year: 2000

Volume: 65

Issue: 22

Pages: 7417-7421

ISSN (print): 0022-3263

ISSN (electronic): 1520-6904

Publisher: American Chemical Society

URL: http://dx.doi.org/10.1021/jo000558p

DOI: 10.1021/jo000558p

PubMed id: 11076598


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