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Lewis-Acid-Promoted Ligand-Controlled Regiodivergent Cycloaddition of Pd-Oxyallyl with 1,3-Dienes: Reaction Development and Origins of Selectivities

Weiwei Chai, Qingyang Zhou, Wenna Ai, Yin Zheng, Tianzhu Qin, Xiufang Xu* and Weiwei Zi*

*College of Chemistry, Nankai University, Tianjin 300071, China, Email:,

W. Chai, Q. Zhou, W. Ai, Y. Zheng, T. Qin, X. Xu, W. Zi, J. Am. Chem. Soc., 2021, 143, 3595-3603.

DOI: 10.1021/jacs.0c13412

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Lithium triflate-promoted (3 + 2) cycloaddition reactions of palladium-oxyallyl species with 1,3-dienes provide cyclopentanones via a pathway terminated with C-C bond formation. Furthermore, by tuning the steric properties of the palladium ligand, the competing (4 + 3) cycloadditions enable regiodivergent access to cycloheptanones.

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proposed reaction pathway

Key Words


ID: J48-Y2021