Palladium-Catalyzed Tandem Ester Dance/Decarbonylative Coupling Reactions.

Dance reaction" on the aromatic ring is a powerful method in organic chemistry to translocate functional groups on arene scaffolds. Notably, dance reactions of halides and pseudohalides offer a unique platform for the divergent synthesis of substituted (hetero)aromatic compounds when combined with transition-metal-catalyzed coupling reactions. Herein, we report a tandem reaction of ester dance and decarbonylative coupling enabled by palladium catalysis. In this reaction, 1,2-translocation of the ester moiety on the aromatic ring is followed by decarbonylative coupling with nucleophiles to enable the installation of a variety of nucleophiles at the position adjacent to the ester in the starting material.

Citation

Masayuki Kubo, Naomi Inayama, Eisuke Ota, Junichiro Yamaguchi. Palladium-Catalyzed Tandem Ester Dance/Decarbonylative Coupling Reactions. Organic letters. 2022 Jun 03;24(21):3855-3860

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PMID: 35604648

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