Regioselective alkenylation of imidazoles by nickel/Lewis acid catalysis

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

doi:10.1016/j.tetlet.2009.02.195

Regioselective alkenylation of imidazoles by nickel/Lewis acid catalysis

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

58 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 language	English
Pages (from-to)	3463-3466
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2009.02.195
Publication status	Published - 2009 Jul 1
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Regioselective alkenylation of imidazoles by nickel/Lewis acid catalysis",

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.",

author = "Kanyiva, {Kyalo Stephen} and Florian L{\"o}bermann and Yoshiaki Nakao and Tamejiro Hiyama",

note = "Funding Information: This work has been supported by Grant-in-Aid for Creative Scientific Research and that for Priority Area {\textquoteleft}Chemistry of Concerto Catalysis{\textquoteright} from MEXT. K.S.K. acknowledges Honjo International Scholarship Foundation for financial support. ",

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doi = "10.1016/j.tetlet.2009.02.195",

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T1 - Regioselective alkenylation of imidazoles by nickel/Lewis acid catalysis

AU - Kanyiva, Kyalo Stephen

AU - Löbermann, Florian

AU - Nakao, Yoshiaki

AU - Hiyama, Tamejiro

N1 - Funding Information: This work has been supported by Grant-in-Aid for Creative Scientific Research and that for Priority Area ‘Chemistry of Concerto Catalysis’ from MEXT. K.S.K. acknowledges Honjo International Scholarship Foundation for financial support.

PY - 2009/7/1

Y1 - 2009/7/1

N2 - 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.

AB - 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.

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DO - 10.1016/j.tetlet.2009.02.195

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JO - Tetrahedron Letters

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Regioselective alkenylation of imidazoles by nickel/Lewis acid catalysis

Abstract

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