A strategy for CH activation of pyridines: direct C-2 selective alkenylation of pyridines by nickel/Lewis acid catalysis

Y Nakao, KS Kanyiva, T Hiyama

Index: Nakao, Yoshiaki; Kanyiva, Kyalo Stephen; Oda, Shinichi; Hiyama, Tamejiro Journal of the American Chemical Society, 2006 , vol. 128, # 25 p. 8146 - 8147

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Citation Number: 265

Abstract

The C-2 selective alkenylation of pyridine derivatives is achieved with a catalyst consisting of nickel and Lewis acid. Use of diorganozinc compounds as the Lewis acid catalyst gives C- 2 monoalkenylation products, whereas AlMe3 changes the reaction course to afford C-2 dienylated products, which are derived from double insertion of alkynes into the C (2)-H bond. The reaction demonstrates a broad substrate scope and proceeds with high chemo- ...