Synthesis of [60]Fullerene-Fused Spiroindanes by Palladium-Catalyzed Oxidative Annulation of [60]Fullerene with 2-Aryl Cyclic 1,3-Dicarbonyl Compounds

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• 作者：Dian-Bing Zhou ; Guan-Wu Wang
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：June 3, 2016
• 年：2016
• 卷：18
• 期：11
• 页码：2616-2619
• 全文大小：334K
• 年卷期：0
• ISSN：1523-7052

文摘

A convenient and facile palladium-catalyzed reaction of [60]fullerene (C₆₀) with 2-aryl cyclic 1,3-dicarbonyl compounds via the enolate-directed sp² C–H activation and sp³ C–H functionalization has been exploited to synthesize the novel and rare C₆₀-fused spiroindanes for the first time. This reaction is easy to perform with broad substrate scope and provides diversified products in 20–50% yields. A plausible reaction mechanism involving the palladium-catalyzed enolate-directed C–H activation and subsequent cyclization has been proposed, and the electrochemistry of the C₆₀-fused spiroindanes has also been investigated.