Cycloisomerization versus Hydration Reactions in Aqueous Media: A Au(III)-NHC Catalyst That Makes the Difference

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• 作者：Eder Tom谩s-Mendivil ; Patrick Y. Toullec ; Josefina D铆ez ; Salvador Conejero ; V茅ronique Michelet ; Victorio Cadierno
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：May 18, 2012
• 年：2012
• 卷：14
• 期：10
• 页码：2520-2523
• 全文大小：210K
• 年卷期：v.14,no.10(May 18, 2012)
• ISSN：1523-7052

文摘

A novel water-soluble Au(III)-NHC complex has been synthesized and successfully applied in the intramolecular cyclization of 纬-alkynoic acids into enol-lactones under biphasic toluene/water conditions, thus representing a rare example of an active and selective catalyst for this transformation in aqueous media. Remarkably, competing alkyne hydration processes were not observed, even during the desymmetrization reaction of challenging 1,6-diyne substrates. In addition, after phase separation, the water-soluble Au(III) catalyst could be recycled 10 times without loss of activity or selectivity.