Collective Synthesis of Phenanthridinone through C–H Activation Involving a Pd-Catalyzed Aryne Multicomponent Reaction

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• 作者：Minghao Feng ; Bingqing Tang ; Hong-Xi Xu ; Xuefeng Jiang
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：September 2, 2016
• 年：2016
• 卷：18
• 期：17
• 页码：4352-4355
• 全文大小：390K
• 年卷期：0
• ISSN：1523-7052

文摘

A palladium-catalyzed multicomponent reaction (MCR) involving aryne, CO, and aniline is established for straightforward assembly of a phenanthridinone scaffold through C–H bond activation. Free combination with multiple kinds of readily available anilines and arynes is facilely achieved for phenanthridinone construction without prefunctionalization. Representative natural products were subsequently synthesized through this MCR strategy highly efficiently. Control experiments and interval NMR tracking revealed the mechanism, particularly the key role of CuF₂ in determining the aryne-releasing rate from the precursor in this transformation.