Issue 5, 2013

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
13 Feb 2013
Accepted
07 Mar 2013
First published
14 Mar 2013

Chem. Sci., 2013,4, 2241-2247

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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