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Bidentate N-ligand-assisted gold redox catalysis with hydrogen peroxide

Nature Chemistry volume 17, pages 822–834 (2025)Cite this article

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Abstract

Gold redox catalysis, which exploits the ability of strong π-acid activation in combination with redox reactions, has emerged as an attractive synthetic method with unique reactivities compared to other transition metals. However, gold redox chemistry bears the challenge to overcome the high redox potential of Au(I)/Au(III) (1.41 V). The classical strategy of gold redox catalysis applies strong external chemical oxidants which inevitably results in low atom economy and substrate limitations due to incompatibility with functional groups. Here we report a bidentate N-ligand (for example, Phen, Bpy) assisted gold redox catalysis using H2O2 as oxidant, which proved to be generally applicable for many forms of coupling reactions. In addition, C(sp2)–C(sp2) bicyclization coupling (cross-coupling of two cyclized substrates) is accessible under our conditions. Mechanistic studies reveal a redox elimination process in which a bidentate N-ligand is crucial for the catalytic cycle. The formation of alkynyl-AuIII–OH and vinyl-AuIII–OH species is the key process for the synergistic π-bond activation and AuI oxidation.

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Fig. 1: Gold redox catalysis and our strategy.
Fig. 2: Comprehensive synthetic applications.
Fig. 3: Mechanistic studies.
Fig. 4: Plausible reaction pathway.

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Data availability

The data supporting the findings of this work are provided in the Supplementary Information, including experimental procedures and characterization of new compounds. Crystallographic data for the structures reported in this Article have been deposited at the Cambridge Crystallographic Data Centre, under deposition numbers CCDC 2372959 (3au), CCDC 2180908 (9al), CCDC 2218248 (11m), CCDC 2218295 (11u), CCDC 2372960 (12h) and CCDC 2372961 (12l). Copies of the data can be obtained free of charge via https://www.ccdc.cam.ac.uk/structures/.

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Acknowledgements

H.S., Y.T., Y.L. and T.W. are grateful for PhD fellowships from the China Scholarship Council (CSC). H.S. gratefully acknowledges the CPSF (number GZC20230165) and the NSFC (number 22401010). J.L. gratefully acknowledges the Alexander von Humboldt Foundation for a postdoctoral fellowship. H.H., P.M.S. and A.S.K.H. gratefully acknowledge the Hector Fellow Academy for the generous provision of funding. H.S. and N.J. acknowledge the NSFC (numbers 22293014, 22131002, 22161142019), the National Key R&D Program of China (number 2021YFA1501700), Changping Laboratory, the New Cornerstone Science Foundation through the New Cornerstone Investigator Program and the XPLORER PRIZE for financial support. We thank X. Zhang for his help with the ESI-MS mechanism experiments.

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Authors and Affiliations

  1. Organisch-Chemisches Institut, Heidelberg University, Heidelberg, Germany

    Hongwei Shi, Matthias Rudolph, Jun Li, Yu Tian, Martin C. Dietl, Hadil Alshurafa, Yaowen Liu, Tao Wang, Henrik Habeck, Philipp M. Stein, Petra Krämer, Frank Rominger, Thomas Oeser & A. Stephen K. Hashmi

  2. State Key Laboratory of Natural and Biomimetic Drugs, Chemical Biology Center, School of Pharmaceutical Sciences, Peking University, Beijing, China

    Hongwei Shi & Ning Jiao

  3. Changping Laboratory, Beijing, China

    Ning Jiao

  4. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China

    Ning Jiao

  5. Chemistry Department, Faculty of Science, King Abdulaziz University (KAU), Jeddah, Saudi Arabia

    A. Stephen K. Hashmi

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Contributions

H.S. conceived and designed the experiments. A.S.K.H. and N.J. directed the research. H.S. carried out most of the experiments. H.S., M.R., J.L., Y.T., M.C.D., H.A., Y.L., T.W., H.H., P.M.S., N.J. and A.S.K.H. participated in discussion. P.K. analysed IR data. F.R. and T.O. conducted X-ray crystal structure analysis. H.S., M.R., N.J. and A.S.K.H. wrote the paper.

Corresponding authors

Correspondence to Ning Jiao or A. Stephen K. Hashmi.

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The authors declare no competing interests.

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Nature Chemistry thanks Nitin Patil, Xiaodong Shi and the other, anonymous, reviewer(s) for their contribution to the peer review of this work.

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Supplementary information

Supplementary Information (download PDF )

Supplementary data, figures, tables and discussion.

Supplementary Data 1

Crystallographic data for compound 3au; CCDC reference 2372959

Supplementary Data 2

Crystallographic data for compound 9al; CCDC reference 2180908

Supplementary Data 3

Crystallographic data for compound 11m; CCDC reference 2218248

Supplementary Data 4

Crystallographic data for compound 11u; CCDC reference 2218295

Supplementary Data 5

Crystallographic data for compound 12h; CCDC reference 2372960

Supplementary Data 6

Crystallographic data for compound 12l; CCDC reference 2372961

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Shi, H., Rudolph, M., Li, J. et al. Bidentate N-ligand-assisted gold redox catalysis with hydrogen peroxide. Nat. Chem. 17, 822–834 (2025). https://doi.org/10.1038/s41557-025-01835-7

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