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通过二元酸策略实现芳基乙烯基酮的催化 Nazarov 反应。

Catalytic Nazarov reaction of aryl vinyl ketones via binary acid strategy.

机构信息

Department of Chemistry and State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, 300071, China.

出版信息

J Org Chem. 2013 Jan 18;78(2):606-13. doi: 10.1021/jo302451b. Epub 2012 Dec 28.

Abstract

We describe herein a viable binary acid strategy for the catalytic Nazarov reaction of aryl vinyl ketones. Simply combining a Lewis acid and a Brønsted acid led to a dramatic enhancement of the catalytic activity in the Nazarov reaction of aryl vinyl β-ketoesters. The obtained optimal binary acid catalyst In(OTf)(3)/diphenyl phosphoric acid (DPP) can be applied to a range of aryl vinyl ketones with good activity. A trend of reactivity has also been summarized on the basis of mapping of the substituents.

摘要

我们在此描述了一种可行的二元酸催化 Nazarov 反应的策略,用于芳基乙烯基酮。只需将路易斯酸和布朗斯特酸结合,就可以显著提高芳基乙烯基β-酮酯的 Nazarov 反应的催化活性。所得到的最佳二元酸催化剂 In(OTf)(3)/二苯膦酸(DPP)可用于一系列具有良好活性的芳基乙烯基酮。还根据取代基的映射总结了反应性的趋势。

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