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Programmable divergent electrochemical ring-opening multifunctionalization of strained rings

Nature Chemistry volume 18, pages 656–668 (2026) Cite this article

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Abstract

The ring-opening functionalization of strained rings represents a highly valuable transformation. However, existing strategies predominantly focus on ring-opening difunctionalization, as initial derivatization typically diminishes the reactivity of surrounding C–H bonds. Consequently, the selective control over site, regio and oxidation state among multiple inert C–H/C–C bonds remains a major unmet challenge. Here we report a multisite programmable, divergent ring-opening functionalization of strained rings via electro-oxidation of continuous C–C bond and multiple C(sp3)–H bonds. The key to this strategy is the generation of olefins through a controlled ‘olefin slow-release pool’, which ensures sufficient selectivity oxidation and suppresses undesired polymerization. Specifically, precise trioxygenation, tetraoxygenation and trihalohydroxylation have been realized, accompanied by controllable remote alkenylation via direct current electrolysis, rapid alternating polarity electrolysis and electrophotocatalysis. This versatile method enables facile transformation of readily accessible strained rings into diverse multi-oxygenated scaffolds, including oxazolines, polyols, polyhalogenated alcohols, as well as bicyclic frameworks via skeletal editing.

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Fig. 1: Ring-opening multifunctionalization of strained rings.
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Data availability

All data generated in this study are provided within the article and its Supplementary Information. Crystallographic data for the structures reported in this Article have been deposited at the Cam bridge Crystallographic Data Centre, under deposition numbers CCDC 2485252 (2z), CCDC 2442144 (6e), CCDC 2446154 (19a), CCDC 2496274 (19b), and CCDC: 2495783 (34). Copies of the data can be obtained free of charge via https://www.ccdc.cam.ac.uk/structures/.

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Acknowledgements

We are grateful for financial support from National Natural Science Foundation of China (grant nos. 22471156, 22301179 and 22401164), Fundamental Research Funds for the Central Universities (grant nos. 25×010202131, 24×010301678), Excellent Young Scientists Fund Program (overseas) and Shanghai Jiao Tong University 2030 Initiative (grant no. WH510363003/014), Shanghai QiYuan Innovation Foundation, Shanghai Municipal Science and Technology Major Project, New Generation Artificial Intelligence-National Science and Technology Major Project (grant no. 2025ZD0121904), Fujian Province Natural Science Foundation (grant no. 2021J05280) and Fujian Province Talent Introduction Program Foundation (grant no. 01102801). T.S. is a Xiaomi Young Scholar, Tang Scholar. We are grateful to N. Jiao, A. Stephen, K. Hashmi and G. Dong for their invaluable discussion regarding the reaction mechanism.

Author information

Authors and Affiliations

  1. Frontiers Science Center for Transformative Molecules, State Key Laboratory of Synergistic Chem-Bio Synthesis, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong University, Shanghai, People’s Republic of China

    Yajuan Li, Shu-Fan He & Tao Shen

  2. Eastern Institute for Advanced Study, Eastern Institute of Technology, Ningbo, People’s Republic of China

    Yatao Lang, Yong Jiang & Chen Zhu

  3. Department of Respiratory and Critical Care Medicine, Zhongshan Hospital of Xiamen University, School of Medicine, Xiamen University, Xiamen, People’s Republic of China

    Daixi Li

  4. Departrent of Pulmnonary and Critical Care Medicine, Shanghai East Hospital, Tongji University, Shanghai, People’s Republic of China

    Daixi Li

  5. College of Chemistry and Molecular Sciences, Henan University, Zhengzhou, People’s Republic of China

    Ke-Xin Liu & Wenying Ai

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  1. Yajuan Li
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Contributions

T.S. conceived of and directed the project and prepared the paper. T.S., C.Z., Y. Li, D.L., W.A. and Y. Lang designed experiments. Y. Li, S.-F.H., Y. Lang, D.L., Y.J. and K.-X.L. performed the experiments and analysed the data. All the authors participated in the discussion and preparation of the paper.

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Correspondence to Daixi Li, Wenying Ai, Chen Zhu or Tao Shen.

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Extended data

Extended Data Fig. 1 Derivatization of compound 22b and 2z.

a, Derivatization of compound 22b. b, Derivatization of compound 2z. Detailed reaction conditions are provided in General procedure J (GP J) and General procedure K (GP K) in supplementary information.

Extended Data Fig. 2 Mechanism Investigation and proposed mechanism.

a, Cyclic voltammetry studies. b, Investigation of the role of the olefin slow-release pool. c, Control reactions for tetraoxygenation of aminocyclopropanes. d, Comparison of AC and DC electrolysis with different anode materials. e, Mechanism investigation of O2 activation-induced ring-opening skeletal editing.

Extended Data Fig. 3 DFT calculations.

a, DFT calculation of ring-opening tetraoxygenation of cyclobutaneamide. b, DFT calculation of the ring-opening tetraoxygenation of cyclopropaneamide.

Extended Data Fig. 4 Proposed mechanism.

a, Proposed mechanism of multi-oxygenation aminocyclopropanes/butanes. b, Proposed mechanism of O2 activation-induced ring-opening skeletal editing.

Supplementary information

Supplementary Information (download PDF )

Supplementary Figs. 1–58, Tables 1–30 and Discussion.

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Li, Y., Lang, Y., He, SF. et al. Programmable divergent electrochemical ring-opening multifunctionalization of strained rings. Nat. Chem. 18, 656–668 (2026). https://doi.org/10.1038/s41557-026-02110-z

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