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

Posted on 25.11.2021 - 17:33
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.

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Jiang, Guomin; Ye, Hao; Shi, Lei; Dai, Hong; Wu, Xin-Xing (2021): Palladium-Catalyzed Sequential Vinyl C–H Activation/Dual Decarboxylation: Regioselective Synthesis of Phenanthrenes and Cyclohepta[1,2,3-de]naphthalenes. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.1c03517
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