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Recent advances in homogeneous nickel catalysis

Nature volume 509, pages 299–309 (2014)Cite this article

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An Erratum to this article was published on 14 May 2014

Abstract

Tremendous advances have been made in nickel catalysis over the past decade. Several key properties of nickel, such as facile oxidative addition and ready access to multiple oxidation states, have allowed the development of a broad range of innovative reactions. In recent years, these properties have been increasingly understood and used to perform transformations long considered exceptionally challenging. Here we discuss some of the most recent and significant developments in homogeneous nickel catalysis, with an emphasis on both synthetic outcome and mechanism.

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Figure 1: Nickel fundamentals.
Figure 2: Recent nickel-catalysed Suzuki–Miyaura arylations.
Figure 3: Halogen alternatives used in cross-coupling reactions.
Figure 4: Milestones in cross-coupling reactions of aryl ethers and esters.
Figure 5: Reactions of benzylic alcohols and alcohol derivatives.
Figure 6: Nickel-catalysed Negishi-type cross-coupling of aromatic and aliphatic aziridines.
Figure 7: Key representative examples of cross-coupling reactions involving oxidative addition to sp3 carbon electrophiles.
Figure 8: Proposed mechanisms for C(sp3)–C(sp3) cross-coupling.
Figure 9: Asymmetric C(sp3)–C(sp3) cross-coupling reactions.
Figure 10: Reductive cross-coupling reactions.
Figure 11: Selected examples of nickel-catalysed C–H activation reactions.
Figure 12: Nickel-catalysed Heck reactions.
Figure 13: Prototypical reductive coupling reactions and use of new reducing agents.
Figure 14: Two strategies for regiocontrol in reductive coupling reactions.

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Acknowledgements

This work was supported by the NIGMS (GM62755) and the NSF (Graduate Research Fellowship to S.Z.T. and E.A.S.).

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Author notes

  1. Sarah Z. Tasker and Eric A. Standley: These authors contributed equally to this work.

Authors and Affiliations

  1. Department of Chemistry, Massachusetts Institute of Technology, Cambridge, 02139, Massachusetts, USA

    Sarah Z. Tasker, Eric A. Standley & Timothy F. Jamison

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  1. Sarah Z. Tasker
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  2. Eric A. Standley
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  3. Timothy F. Jamison
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Contributions

S.Z.T. and E.A.S. worked together to outline and write the content, and T.F.J. helped edit the manuscript, references and figures.

Corresponding author

Correspondence to Timothy F. Jamison.

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The authors declare no competing financial interests.

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Tasker, S., Standley, E. & Jamison, T. Recent advances in homogeneous nickel catalysis. Nature 509, 299–309 (2014). https://doi.org/10.1038/nature13274

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