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Palladium-Catalyzed [3 + 2] Annulation of Aromatic Amides with Maleimides through Dual C-H Activation.

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A palladium-catalyzed [3 + 2] annulation of substituted aromatic amides with maleimides providing tricyclic heterocyclic molecules in good to moderate yields through weak carbonyl chelation is reported. The reaction proceeds… Click to show full abstract

A palladium-catalyzed [3 + 2] annulation of substituted aromatic amides with maleimides providing tricyclic heterocyclic molecules in good to moderate yields through weak carbonyl chelation is reported. The reaction proceeds via a dual C-H bond activation where the first C-H activation takes place selectively at the benzylic position followed by a second C-H bond activation at the meta position to afford a five-membered cyclic ring. An external ligand Ac-Gly-OH has been used to succeed in this protocol. A plausible reaction mechanism has been proposed for the [3 + 2] annulation reaction.

Keywords: catalyzed annulation; palladium catalyzed; annulation; amides maleimides; aromatic amides; activation

Journal Title: Organic letters
Year Published: 2023

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