Nickel-catalyzed Cycloaddition of α,β-Unsaturated Oximes with Alkynes: Synthesis of Highly Substituted Pyridine Derivatives

• Yuji Yoshida

  Department of Material Chemistry, Graduate School of Engineering, Kyoto University

• Takuya Kurahashi

  Department of Material Chemistry, Graduate School of Engineering, Kyoto University

• Seijiro Matsubara

  Department of Material Chemistry, Graduate School of Engineering, Kyoto University

Abstract

A nickel-catalyzed cycloaddition of α,β-unsaturated oximes with alkynes to afford 2,3,4,6-tetrasubstituted pyridine derivatives has been developed. The reaction involves oxidative addition of the N–O bond of α,β-unsaturated oximes to Ni(0) and subsequent alkyne insertion to an N–Ni bond, followed by intramolecular cyclization. It was also found that β,γ-unsaturated oximes participate in the nickel-catalyzed reaction with alkynes to furnish pyridine derivatives.

Journal

• Chemistry Letters

  Chemistry Letters 41 (11), 1498-1499, 2012-11

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360565169065063296
• NII Article ID: 130004426437
• DOI: 10.1246/cl.2012.1498
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/41/11/1498/55634888/cl.2012.1498.pdf
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