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Synthesis of 2-Arylpiperidines via Pd-Catalyzed Arylation of Aza-Achmatowicz Rearrangement Products with Arylboronic Acids

Guodong Zhao, Daniel P. Canterbury, Alexandria P. Taylor, Xiayun Cheng, Peter Mikochik, Scott W. Bagley and Rongbiao Tong*

*Department of Chemistry, The Hong Kong University of Science and Technology, Clearwater Bay, Kowloon, Hong Kong, China, Email: rtongust.hk

G. Zhao, D. P. Canterbury, A. P. Taylor, X. Cheng, P. Mikochik, S. W. Bagley, R. Tong, Org. Lett., 2020, 22, 458-463.

DOI: 10.1021/acs.orglett.9b04220 (free Supporting Information)


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Abstract

A Pd-catalyzed arylation of aza-Achmatowicz rearrangement products with arylboronic acids provides 2-aryldihydropyridinones for facile synthesis of highly functionalized 2-arylpiperidines. Key to this arylation is the use of non-phosphine-ligand palladium precatalyst. The utility of 2-aryldihydropyridinones is illustrated by the synthesis of a small collection of 2-arylpiperidines.

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Key Words

N-heterocycles


ID: J54-Y2020