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Cooperative H2 activation at a nickel(0)–olefin centre

Nature Chemistry volume 16, pages 417–425 (2024)Cite this article

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Abstract

Catalytic olefin hydrogenation is ubiquitous in organic synthesis. In most proposed homogeneous catalytic cycles, reactive M–H bonds are generated either by oxidative addition of H2 to a metal centre or by deprotonation of a non-classical metal dihydrogen (M–H2) intermediate. Here we provide evidence for an alternative H2-activation mechanism that instead involves direct ligand-to-ligand hydrogen transfer (LLHT) from a metal-bound H2 molecule to a metal-coordinated olefin. An unusual pincer ligand that features two phosphine ligands and a central olefin supports the formation of a non-classical Ni–H2 complex and the Ni(alkyl)(hydrido) product of LLHT, in rapid equilibrium with dissolved H2. The usefulness of this cooperative H2-activation mechanism for catalysis is demonstrated in the semihydrogenation of diphenylacetylene. Experimental and computational mechanistic investigations support the central role of LLHT for H2 activation and catalytic semihydrogenation. The product distribution obtained is largely determined by the competition between (E)–(Z) isomerization and catalyst degradation by self-hydrogenation.

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Fig. 1: Strategies for H2 activation in homogeneous catalysis.
Fig. 2: Cooperative activation of H2 by a nickel/olefin complex.
Fig. 3: Computational studies of H2 activation by a nickel/olefin complex.
Fig. 4: Catalytic semihydrogenation of diphenylacetylene.
Fig. 5: Computed catalytic cycles for semihydrogenation of diphenylacetylene and (Z)-stilbene isomerization, and computed pathway for the formation of complex 5.

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Data availability

The data supporting the findings of this study are provided in the Article and its Supplementary Information and are also available from the corresponding author on reasonable request. Further experimental details, spectra of compounds, crystallographic details and additional discussions of computational details are provided in the Supplementary Information. Coordinates of all computed structures (energy minima and transitions states) are provided in the .xyz format. CCDC 2236144 (compound 5) contains the Supplementary Data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Source Data are provided with this paper.

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Acknowledgements

This project has received funding from the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation program (grant agreement no. 715060). The X-ray diffractometer has been financed by the Netherlands Organization for Scientific Research (NWO). This work made use of the Dutch national e-infrastructure with the support of the SURF Cooperative using grants no. EINF-1254 and EINF-3520. The funders had no role in study design, data collection and analysis, decision to publish or preparation of the manuscript. We thank P. M. Pérez-García for his assistance with the analysis of the catalysis results and helpful discussions. We thank G. van Koten, W. Hill Harman, D. L. J. Broere and A. A. Thevenon-Kozub for insightful discussions.

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Authors and Affiliations

  1. Organic Chemistry and Catalysis, Institute for Sustainable and Circular Chemistry, Faculty of Science, Utrecht University, Utrecht, the Netherlands

    María L. G. Sansores-Paredes & Marc-Etienne Moret

  2. Structural Biochemistry, Bijvoet Centre for Biomolecular Research, Faculty of Science, Utrecht University, Utrecht, the Netherlands

    Martin Lutz

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Contributions

M.-E.M. initiated and supervised the project. M.L.G.S-P. performed the experiments and DFT calculations. M.L. oversaw the acquisition, solving and interpretation of X-ray diffraction of the crystal structure. M.L.G.S-P. and M.-E.M. wrote the manuscript with the contribution of M.L. All authors approved the final manuscript.

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Correspondence to Marc-Etienne Moret.

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Supplementary information

Supplementary Information

Experimental Details, Sections 1–5, Figs. 1–82 and Tables 1–4.

Supplementary Data 1

Coordinates of all computed structures in.xyz format.

Supplementary Data 2

Crystallographic data for compound 5 (CCDC no. 2236144).

Supplementary Data 3

Source numerical data from NMR integration for Supplementary Figs. 20, 21, 26, 29, 30.

Source data

Source Data Fig. 4

Numerical data from NMR integration for Fig. 4.

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Sansores-Paredes, M.L.G., Lutz, M. & Moret, ME. Cooperative H2 activation at a nickel(0)–olefin centre. Nat. Chem. 16, 417–425 (2024). https://doi.org/10.1038/s41557-023-01380-1

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