Zn/CuI-Mediated Coupling of Alkyl Halides with Vinyl Sulfones, Vinyl Sulfonates, and Vinyl Sulfonamides

A novel high-yielding Zn/CuI-mediated coupling method of alkyl halides with vinyl sulfones, vinyl sulfonates, and vinyl sulfonamides is described. This protocol is applicable for primary, secondary, and tertiary alkyl iodides and bromides. Alkyl chlorides and aryl and vinyl halides were unreactive u...

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Veröffentlicht in:	Journal of organic chemistry 2005-08, Vol.70 (17), p.6944-6947
Hauptverfasser:	Zhao, Matthew M, Qu, Chuanxing, Lynch, Joseph E
Format:	Artikel
Sprache:	eng
Schlagworte:	Aliphatic compounds Chemistry Copper - chemistry Exact sciences and technology Halogens - chemistry Magnetic Resonance Spectroscopy Organic chemistry Preparations and properties Sulfonamides - chemistry Sulfones - chemistry Sulfonic Acids - chemistry Zinc - chemistry
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Beschreibung
Zusammenfassung:	A novel high-yielding Zn/CuI-mediated coupling method of alkyl halides with vinyl sulfones, vinyl sulfonates, and vinyl sulfonamides is described. This protocol is applicable for primary, secondary, and tertiary alkyl iodides and bromides. Alkyl chlorides and aryl and vinyl halides were unreactive under the reaction conditions. Formamide was found to be a superior solvent for obtaining high yields.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo050500g