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Palladium-Catalyzed 6-Endo Selective Alkyl-Heck Reactions: Access to 5-Phenyl-1,2,3,6-tetrahydropyridine Derivatives

Xu Dong, Ying Han, Fachao Yan, Qing Liu*, Ping Wang, Kexun Chen, Yueyun Li, Zengdian Zhao, Yunhui Dong and Hui Liu*

*School of Chemical Engineering, Shandong University of Technology, 266 West Xincun Road, Zibo 255049, P. R. China, Email: qingliu0315163.com, huiliu1030sdut.edu.cn

X. Dong, Y. Han, F. Yan, Q. Liu, P. Wang, K. Chen, Y. Li, Z. Zhao, Y. Dong, H. Liu, Org. Lett., 2016, 18, 3758-3761.

DOI: 10.1021/acs.orglett.6b01787 (free Supporting Information)


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Abstract

A palladium-catalyzed highly 6-endo-selective alkyl-Heck reaction of unactivated alkyl iodides provides efficient access to various 5-phenyl-1,2,3,6-tetrahydropyridine derivatives, which are important structural motifs for bioactive molecules. Mechanistic investigations reveal a hybrid palladium-radical process.


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Key Words

N-Heterocycles, Heck Reaction


ID: J54-Y2016