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Palladium-Catalyzed Sequential Vinyl C–H Activation/Dual Decarboxylation: Regioselective Synthesis of Phenanthrenes and Cyclohepta[1,2,3-de]naphthalenes

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journal contribution
posted on 25.11.2021, 17:33 by Guomin Jiang, Hao Ye, Lei Shi, Hong Dai, Xin-Xing Wu
The application of a C­(vinyl), C­(aryl)-palladacycle from vinyl-containing substrates is challenging due to the interference of a reactive double bond in palladium catalysis. This Letter describes a [4 + 2] or [4 + 3] cyclization based on a C­(vinyl), C­(aryl)-palladacycle by employing α-oxocarboxylic acids as the insertion units under a palladium/air system. The reaction proceeded through the key vinyl C–H activation and dual decarboxylation sequence, forming phenanthrenes and cyclohepta­[1,2,3-de]­naphthalenes regioselectively in good yields. The synthetic versatility of this protocol is highlighted by the gram-scale synthesis and synthesizing functional material molecule.