Monomeric three-coordinate N-heterocyclic carbene nickel(I) complexes: Synthesis, structures, and catalytic applications in cross-coupling reactions

Kouki Matsubara, Yukino Fukahori, Takahiro Inatomi, Saeko Tazaki, Yuji Yamada, Yuji Koga, Shinji Kanegawa, Toshikazu Nakamura

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23 Citations (Scopus)

Abstract

A series of three-coordinate monovalent nickel halide complexes bearing N-heterocyclic carbene (NHC) ligands, i.e., NiCl(IPr)(L) [L = pyridine, P(OPh)3, bis(diphenylphosphino)butane (dppb), IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], NiX(IMes)(PPh3) (X = Cl and Br, IMes = 1,3-bis(mesityl)imidazol-2-ylidene), were prepared. The complexes were identified using NMR spectroscopy, superconducting quantum interference device (SQUID), and X-ray crystallography. Additionally, ESR spectra of NiCl(IPr)(pyridine) were taken in toluene. These complexes had three-coordinate Y-shaped geometries in both the solid and solution states. The compounds containing IPr showed equilibrium between the monomeric and dimeric forms, with liberation of ligands. Addition of 1,2-bis(diphenylphosphino)ethane and 1,3-bis(diphenylphosphino)propane to the dinickel(I) IPr complex instead of dppb resulted in heterolytic cleavage to nickel(0) and nickel(II) species. Catalysis of Suzuki cross-coupling and Buchwald-Hartwig amination of aryl bromide using the complexes was investigated. The efficiencies in the amination of aryl bromide depended strongly on the additional donor ligands.

Original languageEnglish
Pages (from-to)3281-3287
Number of pages7
JournalOrganometallics
Volume35
Issue number19
DOIs
Publication statusPublished - Oct 10 2016

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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