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Pd-Catalyzed α-Arylation of Nitriles and Esters and γ-Arylation of Unsaturated Nitriles with TMPZnCl·LiCl

Stephanie Duez, Sebastian Bernhardt, Johannes Heppekausen, Fraser F. Fleming and Paul Knochel*

*Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan, Email: paul.knochelcup.uni-muenchen.de

S. Duez, S. Bernhardt, J. Heppekausen, F. F. Fleming, P. Knochel, Org. Lett., 2011, 13, 1690-1693.

DOI: 10.1021/ol200194y (free Supporting Information)



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Abstract

TMPZnCl·LiCl as a kinetically highly active base enables a Pd-catalyzed α-arylation of nitriles and esters under mild conditions. Remarkably, even a regioselective γ-arylation or a γ-alkenylation of α,β- or β,γ-unsaturated nitriles can be observed.

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Key Words

α-arylation, Nitriles


ID: J54-Y2011-0750