Cu(II)-mediated oxidative dimerization of 2-phenylpyridine derivatives

Xiao Chen, Graham Dobereiner, Xue Shi Hao, Ramesh Giri, Nathan Maugel, Jin Quan Yu

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66 Scopus citations

Abstract

A Cu(II)/I2-mediated C-H bond activation is described. A variety of 2-phenylpyridine derivatives are oxidatively dimerized at the ortho-position of the phenyl ring in which a net loss of two hydrogen atoms results in the formation of a biaryl compound via a double C-H activation/C-C bond-forming process. Moderate functional group tolerance was observed on both the aryl and the pyridyl rings. A single electron transfer (SET) or electrophilic metalation process for iodination followed by Ullmann coupling of the intermediate iodinated product is proposed as the operating mechanism for the dimerization process.

Original languageEnglish (US)
Pages (from-to)3085-3089
Number of pages5
JournalTetrahedron
Volume65
Issue number16
DOIs
StatePublished - Apr 18 2009

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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