IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v14y2023i1d10.1038_s41467-023-40892-9.html
   My bibliography  Save this article

Aqueous pulsed electrochemistry promotes C−N bond formation via a one-pot cascade approach

Author

Listed:
  • Meng He

    (Tianjin University)

  • Yongmeng Wu

    (Tianjin University)

  • Rui Li

    (Tianjin University)

  • Yuting Wang

    (Tianjin University)

  • Cuibo Liu

    (Tianjin University)

  • Bin Zhang

    (Tianjin University)

Abstract

Electrocatalytic C − N bond formation from inorganic nitrogen wastes is an emerging sustainable method for synthesizing organic amines but is limited in reaction scope. Integrating heterogeneous and homogeneous catalysis for one-pot reactions to construct C − N bonds is highly desirable. Herein, we report an aqueous pulsed electrochemistry-mediated transformation of nitrite and arylboronic acids to arylamines with high yields. The overall process involves nitrite electroreduction to ammonia over a Cu nanocoral cathode and subsequent coupling of NH3 with arylboronic acids catalyzed by in situ dissolved Cu(II) under a switched anodic potential. This pulsed protocol also promotes the migration of nucleophilic ArB(OH)3− and causes the consumption of OH− near the cathode surface, accelerating C − N formation and suppressing phenol byproducts. Cu(II) can be recycled via facile electroplating. The wide substrate scope, ready synthesis of 15N-labelled arylamines, and methodological expansion to cycloaddition and Click reactions highlight the great promise.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-40892-9
    DOI: 10.1038/s41467-023-40892-9
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-023-40892-9
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-023-40892-9?utm_source=ideas
    LibKey link: if access is restricted and if your library uses this service, LibKey will redirect you to where you can use your library subscription to access this item
    ---><---

    References listed on IDEAS

    as
    1. Rosa M. Arán-Ais & Fabian Scholten & Sebastian Kunze & Rubén Rizo & Beatriz Roldan Cuenya, 2020. "The role of in situ generated morphological motifs and Cu(i) species in C2+ product selectivity during CO2 pulsed electroreduction," Nature Energy, Nature, vol. 5(4), pages 317-325, April.
    2. Yongmeng Wu & Cuibo Liu & Changhong Wang & Yifu Yu & Yanmei Shi & Bin Zhang, 2021. "Converting copper sulfide to copper with surface sulfur for electrocatalytic alkyne semi-hydrogenation with water," Nature Communications, Nature, vol. 12(1), pages 1-11, December.
    3. Shuai Liu & Xu Cheng, 2022. "Insertion of ammonia into alkenes to build aromatic N-heterocycles," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    4. Yueshen Wu & Zhan Jiang & Zhichao Lin & Yongye Liang & Hailiang Wang, 2021. "Direct electrosynthesis of methylamine from carbon dioxide and nitrate," Nature Sustainability, Nature, vol. 4(8), pages 725-730, August.
    5. Yongmeng Wu & Jinghui Zhao & Changhong Wang & Tieliang Li & Bo-Hang Zhao & Ziyang Song & Cuibo Liu & Bin Zhang, 2023. "Electrosynthesis of a nylon-6 precursor from cyclohexanone and nitrite under ambient conditions," Nature Communications, Nature, vol. 14(1), pages 1-7, December.
    6. Vijaya R. Pattabiraman & Jeffrey W. Bode, 2011. "Rethinking amide bond synthesis," Nature, Nature, vol. 480(7378), pages 471-479, December.
    7. Xin Liu & Yan Jiao & Yao Zheng & Mietek Jaroniec & Shi-Zhang Qiao, 2022. "Mechanism of C-N bonds formation in electrocatalytic urea production revealed by ab initio molecular dynamics simulation," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    Full references (including those not matched with items on IDEAS)

    Citations

    Citations are extracted by the CitEc Project, subscribe to its RSS feed for this item.
    as


    Cited by:

    1. 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.

    Most related items

    These are the items that most often cite the same works as this one and are cited by the same works as this one.
    1. Nannan Meng & Jiang Shao & Hongjiao Li & Yuting Wang & Xiaoli Fu & Cuibo Liu & Yifu Yu & Bin Zhang, 2022. "Electrosynthesis of formamide from methanol and ammonia under ambient conditions," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    2. Yilong Zhao & Yunxuan Ding & Wenlong Li & Chang Liu & Yingzheng Li & Ziqi Zhao & Yu Shan & Fei Li & Licheng Sun & Fusheng Li, 2023. "Efficient urea electrosynthesis from carbon dioxide and nitrate via alternating Cu–W bimetallic C–N coupling sites," Nature Communications, Nature, vol. 14(1), pages 1-12, December.
    3. Jiao Lan & Zengxi Wei & Ying-Rui Lu & DeChao Chen & Shuangliang Zhao & Ting-Shan Chan & Yongwen Tan, 2023. "Efficient electrosynthesis of formamide from carbon monoxide and nitrite on a Ru-dispersed Cu nanocluster catalyst," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    4. Yirong Tang & Zhan Jiang & Yubo Yuan & Li Xu & Chuyao Jin & Bulin Chen & Zhichao Lin & Jie Zao & Jianwei Du & Xiao Zhang & Xiang Gao & Yongye Liang, 2024. "Selective electrosynthesis of hydroxylamine from aqueous nitrate/nitrite by suppressing further reduction," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    5. Yongmeng Wu & Jinghui Zhao & Changhong Wang & Tieliang Li & Bo-Hang Zhao & Ziyang Song & Cuibo Liu & Bin Zhang, 2023. "Electrosynthesis of a nylon-6 precursor from cyclohexanone and nitrite under ambient conditions," Nature Communications, Nature, vol. 14(1), pages 1-7, December.
    6. Xin Liu & Yan Jiao & Yao Zheng & Mietek Jaroniec & Shi-Zhang Qiao, 2022. "Mechanism of C-N bonds formation in electrocatalytic urea production revealed by ab initio molecular dynamics simulation," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    7. Marvin L. Frisch & Longfei Wu & Clément Atlan & Zhe Ren & Madeleine Han & Rémi Tucoulou & Liang Liang & Jiasheng Lu & An Guo & Hong Nhan Nong & Aleks Arinchtein & Michael Sprung & Julie Villanova & Ma, 2023. "Unraveling the synergistic effects of Cu-Ag tandem catalysts during electrochemical CO2 reduction using nanofocused X-ray probes," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    8. Gui Zhao & Jiayi Lin & Mengying Lu & Lina Li & Pengtao Xu & Xi Liu & Liwei Chen, 2024. "Potential cycling boosts the electrochemical conversion of polyethylene terephthalate-derived alcohol into valuable chemicals," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    9. Yinchao Yao & Tong Shi & Wenxing Chen & Jiehua Wu & Yunying Fan & Yichun Liu & Liang Cao & Zhuo Chen, 2024. "A surface strategy boosting the ethylene selectivity for CO2 reduction and in situ mechanistic insights," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    10. Eamonn Murphy & Yuanchao Liu & Ivana Matanovic & Martina Rüscher & Ying Huang & Alvin Ly & Shengyuan Guo & Wenjie Zang & Xingxu Yan & Andrea Martini & Janis Timoshenko & Beatriz Roldán Cuenya & Iryna , 2023. "Elucidating electrochemical nitrate and nitrite reduction over atomically-dispersed transition metal sites," Nature Communications, Nature, vol. 14(1), pages 1-15, December.
    11. Qian Wu & Chencheng Dai & Fanxu Meng & Yan Jiao & Zhichuan J. Xu, 2024. "Potential and electric double-layer effect in electrocatalytic urea synthesis," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    12. Wei Liu & Pengbo Zhai & Aowen Li & Bo Wei & Kunpeng Si & Yi Wei & Xingguo Wang & Guangda Zhu & Qian Chen & Xiaokang Gu & Ruifeng Zhang & Wu Zhou & Yongji Gong, 2022. "Electrochemical CO2 reduction to ethylene by ultrathin CuO nanoplate arrays," Nature Communications, Nature, vol. 13(1), pages 1-12, December.
    13. Hefei Li & Pengfei Wei & Tianfu Liu & Mingrun Li & Chao Wang & Rongtan Li & Jinyu Ye & Zhi-You Zhou & Shi-Gang Sun & Qiang Fu & Dunfeng Gao & Guoxiong Wang & Xinhe Bao, 2024. "CO electrolysis to multicarbon products over grain boundary-rich Cu nanoparticles in membrane electrode assembly electrolyzers," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    14. Yuxing Cai & Yuxin Zhao & Kai Tang & Hong Zhang & Xueling Mo & Jiean Chen & Yong Huang, 2024. "Amide C–N bonds activation by A new variant of bifunctional N-heterocyclic carbene," Nature Communications, Nature, vol. 15(1), pages 1-7, December.
    15. Mengran Li & Erdem Irtem & Hugo-Pieter Iglesias van Montfort & Maryam Abdinejad & Thomas Burdyny, 2022. "Energy comparison of sequential and integrated CO2 capture and electrochemical conversion," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    16. Pritha Ghosh & Nishant Raj & Hitesh Verma & Monika Patel & Sohini Chakraborti & Bhavesh Khatri & Chandrashekar M. Doreswamy & S. R. Anandakumar & Srinivas Seekallu & M. B. Dinesh & Gajanan Jadhav & Pr, 2023. "An amide to thioamide substitution improves the permeability and bioavailability of macrocyclic peptides," Nature Communications, Nature, vol. 14(1), pages 1-14, December.
    17. Yanmei Huang & Caihong He & Chuanqi Cheng & Shuhe Han & Meng He & Yuting Wang & Nannan Meng & Bin Zhang & Qipeng Lu & Yifu Yu, 2023. "Pulsed electroreduction of low-concentration nitrate to ammonia," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    18. Min Liu & Tian Feng & Yanwei Wang & Guangsheng Kou & Qiuyan Wang & Qian Wang & Youai Qiu, 2023. "Metal-free electrochemical dihydroxylation of unactivated alkenes," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    19. Kui Fan & Wenfu Xie & Jinze Li & Yining Sun & Pengcheng Xu & Yang Tang & Zhenhua Li & Mingfei Shao, 2022. "Active hydrogen boosts electrochemical nitrate reduction to ammonia," Nature Communications, Nature, vol. 13(1), pages 1-13, December.
    20. Suheng Wang & Kelechi Uwakwe & Liang Yu & Jinyu Ye & Yuezhou Zhu & Jingting Hu & Ruixue Chen & Zheng Zhang & Zhiyou Zhou & Jianfeng Li & Zhaoxiong Xie & Dehui Deng, 2021. "Highly efficient ethylene production via electrocatalytic hydrogenation of acetylene under mild conditions," Nature Communications, Nature, vol. 12(1), pages 1-9, December.

    More about this item

    Statistics

    Access and download statistics

    Corrections

    All material on this site has been provided by the respective publishers and authors. You can help correct errors and omissions. When requesting a correction, please mention this item's handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-40892-9. See general information about how to correct material in RePEc.

    If you have authored this item and are not yet registered with RePEc, we encourage you to do it here. This allows to link your profile to this item. It also allows you to accept potential citations to this item that we are uncertain about.

    If CitEc recognized a bibliographic reference but did not link an item in RePEc to it, you can help with this form .

    If you know of missing items citing this one, you can help us creating those links by adding the relevant references in the same way as above, for each refering item. If you are a registered author of this item, you may also want to check the "citations" tab in your RePEc Author Service profile, as there may be some citations waiting for confirmation.

    For technical questions regarding this item, or to correct its authors, title, abstract, bibliographic or download information, contact: Sonal Shukla or Springer Nature Abstracting and Indexing (email available below). General contact details of provider: http://www.nature.com .

    Please note that corrections may take a couple of weeks to filter through the various RePEc services.

    IDEAS is a RePEc service. RePEc uses bibliographic data supplied by the respective publishers.