Isolation, structure, and reactivity of an arylnickel(II) pivalate complex in catalytic C-H/C-O biaryl coupling

Kei Muto, Junichiro Yamaguchi, Aiwen Lei, Kenichiro Itami

Research output: Contribution to journalArticle

108 Citations (Scopus)

Abstract

We describe mechanistic studies of a C-H/C-O biaryl coupling of 1,3-azoles and aryl pivalates catalyzed by Ni(cod)2/dcype. This study not only supports a catalytic cycle consisting of C-O oxidative addition, C-H nickelation, and reductive elimination but also provides insight into the dramatic ligand effect in C-H/C-O coupling. We have achieved the first synthesis, isolation and structure elucidation of an arylnickel(II) pivalate, which is an intermediate in the catalytic cycle after oxidative addition of a C-O bond. Furthermore, kinetic studies and kinetic isotope effect investigations reveal that the C-H nickelation is the turnover-limiting step in the catalytic cycle.

Original languageEnglish
Pages (from-to)16384-16387
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number44
DOIs
Publication statusPublished - 2013 Nov 6
Externally publishedYes

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Gadiformes
Azoles
Kinetics
Isotopes
Ligands

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Isolation, structure, and reactivity of an arylnickel(II) pivalate complex in catalytic C-H/C-O biaryl coupling. / Muto, Kei; Yamaguchi, Junichiro; Lei, Aiwen; Itami, Kenichiro.

In: Journal of the American Chemical Society, Vol. 135, No. 44, 06.11.2013, p. 16384-16387.

Research output: Contribution to journalArticle

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