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Electrocatalytic cyclic deracemization enabled by a chemically modified electrode

Nature Catalysis volume 7, pages 878–888 (2024)Cite this article

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Abstract

Redox chemistry, which is frequently encountered in the formation of new bonds and stereocentres, relies on the compatibility of redox potentials. Despite recent advances, achieving a general electrocatalytic cyclic deracemization process without stoichiometric redox reagents remains a formidable challenge. Here we show that electrocatalytic cyclic deracemization of secondary alcohols can be accomplished through sequential iridium-catalysed enantioselective anodic dehydrogenation and rhodium-catalysed cathodic hydrogenation, utilizing metal hydride catalysis. A considerable hurdle arises as stronger hydride donors necessitate parent metal complexes to possess low reduction potentials, resulting in inherent redox potential incompatibility. Nonetheless, we overcame this incompatibility by leveraging a recyclable rhodium-catalyst-modified electrode as the cathode—an accomplishment that homogeneous rhodium catalysis could not achieve. Our approach enables chemoselective stereochemical editing of bioactive compounds with remarkable functional group tolerance. Surface characterization and mechanistic studies showcased the unique advantages conferred by the chemically modified electrode.

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Fig. 1: Electrocatalytic cyclic deracemization.
Fig. 2: Reaction development.
Fig. 3: Substrate scope.
Fig. 4: Synthetic applications.
Fig. 5: Mechanistic studies and characterization.

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Data availability

The data supporting the findings of this study are available within the paper and its Supplementary Information, or from the authors on reasonable request. Crystallographic data for the structures reported in this Article have been deposited at the Cambridge Crystallographic Data Centre, under deposition nos. CCDC 2328338 ((S)-34). Copies of the data can be obtained free of charge at https://www.ccdc.cam.ac.uk/structures/. Source Data are provided with this paper.

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Acknowledgements

We are grateful for financial support from National Key R&D Program of China (grant no. 2022YFA1505100 to J.W.), the National Natural Science Foundation of China (grant no. 22201124 to J.W.), the Guangdong Provincial Key Laboratory of Catalysis (grant no. 2020B121201002 to J.W.) and the Innovation Commission of Shenzhen Municipality (grant no. 20231120100305001 to J.W.). We thank C. Huang for performing experiments during the paper’s revision. We thank the Core Research Facilities for their assistance with performing ICP-MS, SEM and EDS experiments. The theoretical work was supported by the Center for Computational Science and Engineering at SUSTech. We thank X.-Y. Liu (Southern University of Science and Technology), G. Dong (University of Chicago) and Z. Huang (University of Hong Kong) for helpful discussions. We thank J. Gu (Southern University of Science and Technology) for assisting the EDS experiments.

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Authors and Affiliations

  1. Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, China

    Cheng-Jie Zhu, Xiuying Yang & Jianchun Wang

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  1. Cheng-Jie Zhu
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Contributions

J.W. conceived and designed the project. C.-J.Z. discovered the reaction and finished the optimization. C.-J.Z. and X.Y. performed other experiments. J.W. performed the computational work. J.W. and C.-J.Z. co-wrote the paper.

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Correspondence to Jianchun Wang.

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Supplementary information

Supplementary Information

Supplementary Figs. 1–23, Tables 1–6, Methods and References.

Supplementary Data 1

Crystallographic data for (S)-34 (CCDC reference no. 2328338).

Supplementary Data 2

Cartesian coordinates of optimized structures.

Source data

Source Data Fig. 4

The original data for Fig. 4a.

Source Data Fig. 5

The original cyclic voltammetry data for Fig. 5.

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Zhu, CJ., Yang, X. & Wang, J. Electrocatalytic cyclic deracemization enabled by a chemically modified electrode. Nat Catal 7, 878–888 (2024). https://doi.org/10.1038/s41929-024-01189-2

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