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Palladium-Catalyzed Cross-Coupling Reaction of Diazo Compounds and Vinyl Boronic Acids: An Approach to 1,3-Diene Compounds

Yamu Xia, Ying Xia, Zhen Liu, Yan Zhang and Jianbo Wang*

*Beijing National Laboratory of Molecular Sciences (BNLMS), College of Chemistry, Peking University, Beijing 100871, China, Email: wangjbpku.edu.cn

Y. Xia, Y. Xia, Z. Liu, Y. Zhang, J. Wang, J. Org. Chem., 2014, 79, 7711-7717.

DOI: 10.1021/jo5012703 (free Supporting Information)


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Abstract

A palladium-catalyzed oxidative cross-coupling of vinyl boronic acids and cyclic α-diazocarbonyl compounds enables an efficient synthesis of 1,3-diene compounds. Mechanistically, the reaction involves migratory insertion of palladium carbene as the key step.

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Palladium-Catalyzed Cross-Coupling of α-Diazocarbonyl Compounds with Arylboronic Acids

C. Peng, Y. Wang, J. Wang, J. Am. Chem. Soc., 2008, 130, 1566-1567.


Key Words

cyclohexenones, cycloheptenones, 1,3-dienes, benzoquinone


ID: J42-Y2014