Spirocyclization by Palladium-Catalyzed Domino Heck-Direct C-H Arylation Reactions: Synthesis of Spirodihydroquinolin-2-ones. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2012

Spirocyclization by Palladium-Catalyzed Domino Heck-Direct C-H Arylation Reactions: Synthesis of Spirodihydroquinolin-2-ones.

Résumé

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 °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-H functionalization.

Domaines

Chimie organique
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Dates et versions

hal-00742353 , version 1 (16-10-2012)

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Tiffany Piou, Luc Neuville, Jieping Zhu. Spirocyclization by Palladium-Catalyzed Domino Heck-Direct C-H Arylation Reactions: Synthesis of Spirodihydroquinolin-2-ones.. Organic Letters, 2012, 14 (14), pp.3760-3763. ⟨10.1021/ol301616w⟩. ⟨hal-00742353⟩
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