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Copper-Catalyzed Coupling of Amides and Carbamates with Vinyl Halides

Organic Letters · 2003 · Vol. 5(20) · pp. 3667–3669
Lei JiangGabriel E. JobArtis KlaparsStephen L. Buchwald

Abstract

[reaction: see text] A general and efficient copper-catalyzed method for the amidation of vinyl bromides and iodides has been developed. This protocol uses a combination of 5 mol % copper iodide and 20 mol % N,N'-dimethyl ethylenediamine. Substrates bearing ester, silyl ether, and amino groups were successfully coupled under the reaction conditions. The double bond geometry of the vinyl halides was retained under the reaction conditions.

Chemical Synthesis and AnalysisSynthesis and Catalytic ReactionsPeptidase Inhibition and AnalysisChemistryHalideCopperCatalysisSilyl etherSilylationIodideEthylenediamineCoupling reactionEther

MeSH terms

AmidesCarbamatesCatalysisCopperHydrocarbons, IodinatedVinyl Compounds

Funding

  • Pfizer
Citations
398
FWCI
5.81
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References
21
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97%
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