Regioselective alkenylation of imidazoles by nickel/Lewis acid catalysis

Stephen Kyalo Kanyiva, Florian Löbermann, Yoshiaki Nakao, Tamejiro Hiyama

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

Nickel/Lewis acid binary catalysis is found effective to direct regioselective alkenylation of imidazoles through C-H bond activation and stereoselective insertion of alkynes. Use of P(t-Bu)3 as a ligand allows exclusive regioselective C(2)-alkenylation, while PCyp3 is found effective for C(5)-alkenylation of C(2)-substituted imidazoles. The reaction demonstrates a broad scope of imidazoles and internal alkynes to give trisubstituted ethenes highly regio- and stereoselectively in modest to good yields.

Original languageEnglish
Pages (from-to)3463-3466
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number26
DOIs
Publication statusPublished - 2009 Jul 1
Externally publishedYes

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Alkenylation
Imidazoles
Lewis Acids
Nickel
Catalysis
Alkynes
Chemical activation
Ligands

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Regioselective alkenylation of imidazoles by nickel/Lewis acid catalysis. / Kanyiva, Stephen Kyalo; Löbermann, Florian; Nakao, Yoshiaki; Hiyama, Tamejiro.

In: Tetrahedron Letters, Vol. 50, No. 26, 01.07.2009, p. 3463-3466.

Research output: Contribution to journalArticle

Kanyiva, Stephen Kyalo ; Löbermann, Florian ; Nakao, Yoshiaki ; Hiyama, Tamejiro. / Regioselective alkenylation of imidazoles by nickel/Lewis acid catalysis. In: Tetrahedron Letters. 2009 ; Vol. 50, No. 26. pp. 3463-3466.
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