Synthesis of 2-Arylpiperidines via Pd-Catalyzed Arylation of Aza-Achmatowicz Rearrangement Products with Arylboronic Acids
2019
Zhao, Guodong | Canterbury, Daniel P. | Taylor, Alexandria P. | Cheng, Xiayun | Mikochik, Peter | Bagley, Scott W. | Tong, Rongbiao
The first Pd-catalyzed arylation of aza-Achmatowicz rearrangement products with arylboronic acids is achieved, providing versatile 2-aryldihydropyridinones for facile synthesis of highly functionalized 2-arylpiperidines. Key to this arylation is the use of non-phosphine-ligand palladium precatalyst. The substrate scope is demonstrated with >26 examples, and the utility of 2-aryldihydropyridinones is illustrated by the synthesis of a small collection of 2-arylpiperidines with substituents or functional groups at any carbon (C2–C6) as well as two NK₁ receptor antagonists (+)-CP-999,94 and (+)-L-733,060.
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