Nickel(I) Aryl Species: Synthesis, Properties, and Catalytic Activity

Megan Mohadjer Beromi, Gourab Banerjee, Gary W. Brudvig, Nilay Hazari, Brandon Q. Mercado

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

In this work, Ni(I) aryl species that are directly relevant to cross-coupling have been synthesized. Transmetalation of (dppf)NiIX (dppf = 1,1′-bis(diphenylphosphino)-ferrocene, X = Cl, Br) with aryl Grignard reagents or aryl boronic acids in the presence of base produces Ni(I) aryl species of the form (dppf)NiI(Ar) (Ar = Ph, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, 2,4,6-iPr3C6H2). The stability of the Ni(I) aryl species is inversely correlated to the steric bulk on the aryl ligand. The most unstable Ni(I) aryl species are the most active precatalysts for Suzuki-Miyaura reactions because they rapidly decompose to generate the active Ni(0) catalyst. This study shows that Ni(I) aryl species are initially formed in the activation of Ni(I) halide precatalysts for Suzuki-Miyaura reactions and establishes their stoichiometric and catalytic reactivity profile.

Original languageEnglish
Pages (from-to)2526-2533
Number of pages8
JournalACS Catalysis
Volume8
Issue number3
DOIs
Publication statusPublished - Mar 2 2018

Keywords

  • cross-coupling
  • homogeneous catalysis
  • inorganic synthesis
  • mechanism
  • nickel

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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    Mohadjer Beromi, M., Banerjee, G., Brudvig, G. W., Hazari, N., & Mercado, B. Q. (2018). Nickel(I) Aryl Species: Synthesis, Properties, and Catalytic Activity. ACS Catalysis, 8(3), 2526-2533. https://doi.org/10.1021/acscatal.8b00546