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Org Lett. 2016 Aug 5;18(15):3774-7. doi: 10.1021/acs.orglett.6b01787. Epub 2016 Jul 13.

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

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School of Chemical Engineering, Shandong University of Technology , 266 West Xincun Road, Zibo 255049, P. R. China.
College of Materials Science and Engineering, Hunan University , Changsha, Hunan 410082, China.


A new type of palladium-catalyzed 6-endo-selective alkyl-Heck reaction of unactivated alkyl iodides has been described. This strategy provides efficient access to a variety of 5-phenyl-1,2,3,6-tetrahydropyridine derivatives, which are important structural motifs for bioactive molecules. This process displays a broad substrate scope with excellent 6-endo selectivity. Mechanistic investigations reveal that this alkyl-Heck reaction performs via a hybrid palladium-radical process.

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