Dual Catalysis: Proton/Metal-Catalyzed Tandem Benzofuran Annulation/Carbene Transfer Reaction

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• 作者：Jun Ma ; Kai Chen ; Hongguang Fu ; Li Zhang ; Wanqing Wu ; Huanfeng Jiang ; Shifa Zhu
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：March 18, 2016
• 年：2016
• 卷：18
• 期：6
• 页码：1322-1325
• 全文大小：399K
• ISSN：1523-7052

文摘

An efficient proton/metal-catalyzed tandem benzofuran annulation/carbene transfer reaction for the synthesis of various benzofuryl-substituted cyclopropanes and cycloheptatrienes has been developed. The reaction was proposed to proceed through two key intermediates, o-quinone methide (o-QM) and benzofuryl carbene. The DFT-based computational studies indicated that the reaction was initiated through the dehydration of o-HBA via a Brønsted acid mediated proton shuttle transition state, forming the key intermediate o-QM.