Unexpected nickel complex speciation unlocks alternative pathways for the reactions of alkyl halides with dppf-nickel(0)

Megan E. Greaves, Thomas O. Ronson, Guy C. Lloyd-Jones, Feliu Maseras, Stephen Sproules, David J. Nelson

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Abstract

The mechanism of the reactions between dppf-Ni0 complexes and alkyl halides has been investigated using kinetic and mechanistic experiments and DFT calculations. The active species is [Ni(κ2-dppf)(κ1-dppf)], which undergoes a halide abstraction reaction with alkyl halides and rapidly captures the alkyl radical that is formed. The rates of the reactions of [Ni(COD)(dppf)] with alkyl halides and the yields of prototypical nickel-catalysed Kumada cross-coupling reactions of alkyl halides are shown to be significantly improved by the addition of free dppf ligand.
Original languageEnglish
Pages (from-to)10717-10725
Number of pages9
JournalACS Catalysis
Volume10
Early online date21 Aug 2020
DOIs
Publication statusE-pub ahead of print - 21 Aug 2020

Keywords

  • nickel
  • homogenous catalysis
  • cross coupling
  • reaction mechanisms
  • organometallic chemistry

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