Iron-catalyzed Cross-Coupling of Electron-Deficient Heterocycles and Quinone with Organoboron Species via Innate C鈥揌 Functionalization: Application in Total Synthesis of Pyrazine Alkaloid Botryllazine

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• 作者：Parvinder Pal Singh ; Sravan Kumar Aithagani ; Mahipal Yadav ; Varun Pratap Singh ; Ram A. Vishwakarma
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：March 15, 2013
• 年：2013
• 卷：78
• 期：6
• 页码：2639-2648
• 全文大小：491K
• 年卷期：v.78,no.6(March 15, 2013)
• ISSN：1520-6904

文摘

Here, we report an iron-catalyzed cross-coupling reaction of electron-deficient heterocycles and quinone with organoboron species via innate C鈥揌 functionalization. Iron(II) acetylacetonate along with oxidant (K₂S₂O₈) and phase-transfer catalyst (TBAB) under open flask conditions efficiently catalyzed the cross-coupling of pyrazine with arylboronic acids and gave monoarylated products in good to excellent yields. Optimized conditions also worked for other heterocylces such as quinoxalines, pyridines, quinoline, and isoquinoline as well as quinones. In addition, we demonstrated as a first example its application for the synthesis of anticancer marine pyrazine alkaloid botryllazine A.