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Aggregation-induced C–C bond formation on an electrode driven by the surface tension of water

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  • Mengfan Li

    (Nanjing University)

  • Xu Cheng

    (Nanjing University)

Abstract

Electrochemical organic synthesis is typically conducted in organic media. The solvent and related supporting electrolytes negatively affect the greenness of electrosynthesis. In this work, with 100% water used as the solvent, we realize aggregation-driven electrochemical radical cross coupling of unsaturated compounds driven by water tension. A key finding is that aggregation of the substrate at the electrode confined the radical intermediate and prevented side reactions, thus providing a way to regulate radical reactions in addition to their native properties. The reaction provides up to 90% yields with almost quantitative chemoselectivity. The pure water system readily yields the products via cold filtration, and the solvent is recycled repeatedly. In particular, the life span of the radical species generated in the reaction increase significantly because of the confined environment in the aggregation state. The greenness of this protocol is further enhanced with readily separation of product from media using cooling and filtration.

Suggested Citation

  • Mengfan Li & Xu Cheng, 2024. "Aggregation-induced C–C bond formation on an electrode driven by the surface tension of water," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
  • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-52042-w
    DOI: 10.1038/s41467-024-52042-w
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    References listed on IDEAS

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    1. Jiang, H.R. & Shyy, W. & Wu, M.C. & Zhang, R.H. & Zhao, T.S., 2019. "A bi-porous graphite felt electrode with enhanced surface area and catalytic activity for vanadium redox flow batteries," Applied Energy, Elsevier, vol. 233, pages 105-113.
    2. Yong Yuan & Aiwen Lei, 2020. "Is electrosynthesis always green and advantageous compared to traditional methods?," Nature Communications, Nature, vol. 11(1), pages 1-3, December.
    3. Meng He & Yongmeng Wu & Rui Li & Yuting Wang & Cuibo Liu & Bin Zhang, 2023. "Aqueous pulsed electrochemistry promotes C−N bond formation via a one-pot cascade approach," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    4. Rui Li & Yongmeng Wu & Changhong Wang & Meng He & Cuibo Liu & Bin Zhang, 2022. "One-pot H/D exchange and low-coordinated iron electrocatalyzed deuteration of nitriles in D2O to α,β-deuterio aryl ethylamines," Nature Communications, Nature, vol. 13(1), pages 1-12, December.
    5. Xin Huang & Daniel Eggart & Gangqiang Qin & Bidyut Bikash Sarma & Abhijeet Gaur & Jiuzhong Yang & Yang Pan & Mingrun Li & Jianqi Hao & Hongfei Yu & Anna Zimina & Xiaoguang Guo & Jianping Xiao & Jan-Di, 2023. "Methyl radical chemistry in non-oxidative methane activation over metal single sites," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    6. Yuanyuan Xu & Hongwei Chen & Lu Yu & Xichao Peng & Jiawei Zhang & Zhongqiu Xing & Yuyan Bao & Aokun Liu & Yue Zhao & Changlin Tian & Yong Liang & Xiaoqiang Huang, 2024. "A light-driven enzymatic enantioselective radical acylation," Nature, Nature, vol. 625(7993), pages 74-78, January.
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