Spirocyclization by Palladium-Catalyzed Domino Heck鈥揇irect C鈥揌 Arylation Reactions: Synthesis of Spirodihydroquinolin-2-ones

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• 作者：Tiffany Piou ; Luc Neuville ; Jieping Zhu
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：July 20, 2012
• 年：2012
• 卷：14
• 期：14
• 页码：3760-3763
• 全文大小：290K
• 年卷期：v.14,no.14(July 20, 2012)
• ISSN：1523-7052

文摘

Treatment of a DMA solution of anilide 1 with a catalytic amount of palladium acetate (0.025 equiv) and XPhos (0.05 equiv) in the presence of potassium carbonate (2.0 equiv) at 100 掳C afforded dihydroquinolin-2-ones spiro-fused to dihydrofuranyl, indolinyl, and indanyl 2 in good to excellent yields. The reaction went through a domino sequence involving a 5-exo-trig Heck cyclization followed by an intramolecular direct C鈥揌 functionalization.