A strategy for C-H activation of pyridines: Direct C-2 selective alkenylation of pyridines by Nickel/Lewis acid catalysis

Yoshiaki Nakao, Stephen Kyalo Kanyiva, Tamejiro Hiyama

Research output: Contribution to journalArticle

304 Citations (Scopus)

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-, regio-, and stereoselectivities under mild conditions compared with previous examples of direct C-H functionalization of pyridines.

Original languageEnglish
Pages (from-to)2448-2449
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number8
DOIs
Publication statusPublished - 2008 Feb 27
Externally publishedYes

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Alkenylation
Pyridines
Lewis Acids
Nickel
Catalysis
Pyridine
Chemical activation
Stereoselectivity
Regioselectivity
Catalysts
Alkynes
Acids
Derivatives
Substrates

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

A strategy for C-H activation of pyridines : Direct C-2 selective alkenylation of pyridines by Nickel/Lewis acid catalysis. / Nakao, Yoshiaki; Kanyiva, Stephen Kyalo; Hiyama, Tamejiro.

In: Journal of the American Chemical Society, Vol. 130, No. 8, 27.02.2008, p. 2448-2449.

Research output: Contribution to journalArticle

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