I2-Promoted Selective Oxidative Cross-Coupling/Annulation of 2-Naphthols with Methyl Ketones: A Strategy To Build Naphtho[2,1-b]furan-1(2H)-ones with a Quaternary Center

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• 作者：Qinghe Gao ; Xia Wu ; Shan Liu ; Anxin Wu
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：March 21, 2014
• 年：2014
• 卷：16
• 期：6
• 页码：1732-1735
• 全文大小：300K
• 年卷期：v.16,no.6(March 21, 2014)
• ISSN：1523-7052

文摘

A highly efficient and selective molecular iodine-promoted oxidative cross-coupling/annulation between 2-naphthols and methyl ketones has been realized. The reaction successfully constructed a new quaternary carbon center within 3(2H)-furanones. Our synthetic strategy provided an in situ iodination-based oxidative coupling pathway. Based on the experimental results, a self-sequenced iodination/Kornblum oxidation/Friedel鈥揅rafts/oxidation/cyclization mechanism was proposed.