Comparison of dppf-Supported Nickel Precatalysts for the Suzuki-Miyaura Reaction: The Observation and Activity of Nickel(I)

Louise M. Guard, Megan Mohadjer Beromi, Gary W. Brudvig, Nilay Hazari, David J. Vinyard

Research output: Contribution to journalArticle

54 Citations (Scopus)

Abstract

Ni-based precatalysts for the Suzuki-Miyaura reaction have potential chemical and economic advantages compared to commonly used Pd systems. Here, we compare Ni precatalysts for the Suzuki-Miyaura reaction supported by the dppf ligand in 3 oxidation states, 0, I and II. Surprisingly, at 80 °C they give similar catalytic activity, with all systems generating significant amounts of NiI during the reaction. At room temperature a readily accessible bench-stable NiII precatalyst is highly active and can couple synthetically important heterocyclic substrates. Our work conclusively establishes that NiI species are relevant in reactions typically proposed to involve exclusively Ni0 and NiII complexes.

Original languageEnglish
Pages (from-to)13352-13356
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number45
DOIs
Publication statusPublished - Nov 1 2015

Keywords

  • Suzuki-Miyaura coupling
  • cross-coupling
  • homogeneous catalysis
  • nickel
  • reaction mechanism

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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