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Article Dans Une Revue Chemical Science Année : 2013

Ligand-controlled β-selective C(sp3)-H arylation of N-Boc-piperidines

Résumé

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.

Domaines

Catalyse
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Dates et versions

hal-00807150 , version 1 (03-04-2013)

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Citer

Anthony Millet, Paolo Larini, Eric Clot, Olivier Baudoin. Ligand-controlled β-selective C(sp3)-H arylation of N-Boc-piperidines. Chemical Science, 2013, 4, pp.2241-2247. ⟨10.1039/C3SC50428J⟩. ⟨hal-00807150⟩
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