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Issue 5, 2013
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Ligand-controlled β-selective C(sp3)–H arylation of N-Boc-piperidines

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Abstract

We report a general palladium-catalyzed β-arylation of Boc-piperidines, which yields a variety of valuable 3-arylpiperidines in a simple and direct manner. The β- vs. α-arylation selectivity was controlled by the ligand, with flexible biarylphosphines providing mainly the desired β-arylated products whereas more rigid biarylphosphines mainly furnished the more classical α-arylated products. The computed reaction mechanism (DFT), studied from the common α-palladated intermediate, indicated that the reductive elimination steps leading to the α- and β-arylated products are selectivity-determining. Moreover, the experimental trend obtained with different ligands was well reproduced by the calculations.

Graphical abstract: Ligand-controlled β-selective C(sp3)–H arylation of N-Boc-piperidines

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Publication details

The article was received on 13 Feb 2013, accepted on 07 Mar 2013 and first published on 14 Mar 2013


Article type: Edge Article
DOI: 10.1039/C3SC50428J
Citation: Chem. Sci., 2013,4, 2241-2247
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    Ligand-controlled β-selective C(sp3)–H arylation of N-Boc-piperidines

    A. Millet, P. Larini, E. Clot and O. Baudoin, Chem. Sci., 2013, 4, 2241
    DOI: 10.1039/C3SC50428J

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