4.8 Article

Unexpected Nickel Complex Speciation Unlocks Alternative Pathways for the Reactions of Alkyl Halides with dppf-Nickel(0)

Journal

ACS CATALYSIS
Volume 10, Issue 18, Pages 10717-10725

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c02514

Keywords

nickel; homogeneous catalysis; cross-coupling; reaction mechanisms; organometallic chemistry

Funding

  1. AstraZeneca [EP/R512114/1]
  2. Engineering and Physical Sciences Research Council (EPSRC) [EP/R512114/1]
  3. University of Strathclyde
  4. EPSRC [1959228] Funding Source: UKRI

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The mechanism of the reactions between dppf-Ni-0 complexes and alkyl halides has been investigated using kinetic and mechanistic experiments and DFT calculations. The active species is [Ni(kappa(2)-dppf)(kappa(1)-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-catalyzed Kumada cross-coupling reactions of alkyl halides are shown to be significantly improved by the addition of free dppf ligand.

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