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

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 CH functionalization.


Published in:
Organic Letters, 14, 14, 3760-3763
Year:
2012
ISSN:
1523-7052
Keywords:
Laboratories:




 Record created 2012-08-23, last modified 2018-09-13


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