Synthesis of 4-benzylpyridines via Pd-catalyzed CH3-arylation of 4-picoline

Jing Wu; Dadian Wang; Xiang Chen; Qingwen Gui; Hua Li; Ze Tan; Genping Huang; Guangwei Wang

doi:10.1039/C7OB01726J

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Synthesis of 4-benzylpyridines via Pd-catalyzed CH₃-arylation of 4-picoline†

Jing Wu,^ab Dadian Wang,^a Xiang Chen,^a Qingwen Gui,^a Hua Li,^b Ze Tan,

*^a Genping Huang

*^b and Guangwei Wang

*^b

Author affiliations

* Corresponding authors

^a State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China
E-mail: ztanze@gmail.com

^b Department of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. China
E-mail: gphuang@tju.edu.cn, wanggw@tju.edu.cn

Abstract

A highly efficient synthesis of 4-benzylpyridines was developed via Pd-catalyzed C(sp³)–H arylation between 4-picoline and aryl halides. It was found that the best yields were achieved with a simple Pd(PPh₃)₄ catalyst and Cs₂CO₃ as the base. Compared with the known methods, our reaction does not require the use of a strong organometallic reagent as the base.

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Article information

DOI: https://doi.org/10.1039/C7OB01726J
Article type: Communication
Submitted: 13 Jul 2017
Accepted: 24 Aug 2017
First published: 24 Aug 2017

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Org. Biomol. Chem., 2017,15, 7509-7512

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Synthesis of 4-benzylpyridines via Pd-catalyzed CH₃-arylation of 4-picoline

J. Wu, D. Wang, X. Chen, Q. Gui, H. Li, Z. Tan, G. Huang and G. Wang, Org. Biomol. Chem., 2017, 15, 7509 DOI: 10.1039/C7OB01726J

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Organic & Biomolecular Chemistry