IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v14y2023i1d10.1038_s41467-023-42106-8.html
   My bibliography  Save this article

Metal-free electrochemical dihydroxylation of unactivated alkenes

Author

Listed:
  • Min Liu

    (College of Chemistry, Nankai University)

  • Tian Feng

    (College of Chemistry, Nankai University)

  • Yanwei Wang

    (College of Chemistry, Nankai University)

  • Guangsheng Kou

    (College of Chemistry, Nankai University)

  • Qiuyan Wang

    (College of Chemistry, Nankai University)

  • Qian Wang

    (College of Chemistry, Nankai University)

  • Youai Qiu

    (College of Chemistry, Nankai University)

Abstract

Herein, a metal-free electrochemical dihydroxylation of unactivated alkenes is described. The transformation proceeds smoothly under mild conditions with a broad range of unactivated alkenes, providing valuable and versatile dihydroxylated products in moderate to good yields without the addition of costly transition metals and stoichiometric amounts of chemical oxidants. Moreover, this method can be applied to a range of natural products and pharmaceutical derivatives, further demonstrating its synthetic utility. Mechanistic studies have revealed that iodohydrin and epoxide intermediate are formed during the reaction process.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-42106-8
    DOI: 10.1038/s41467-023-42106-8
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-023-42106-8
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-023-42106-8?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. Evan J. Horn & Brandon R. Rosen & Yong Chen & Jiaze Tang & Ke Chen & Martin D. Eastgate & Phil S. Baran, 2016. "Scalable and sustainable electrochemical allylic C–H oxidation," Nature, Nature, vol. 533(7601), pages 77-81, May.
    2. 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.
    3. Chen-Yan Cai & Hai-Chao Xu, 2018. "Dehydrogenative reagent-free annulation of alkenes with diols for the synthesis of saturated O-heterocycles," Nature Communications, Nature, vol. 9(1), pages 1-7, December.
    4. Tian-Jun He & Zongren Ye & Zhuofeng Ke & Jing-Mei Huang, 2019. "Stereoselective synthesis of sulfur-containing β-enaminonitrile derivatives through electrochemical Csp3–H bond oxidative functionalization of acetonitrile," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
    5. Pengfei Li & Chengcheng Guo & Siyi Wang & Dengke Ma & Tian Feng & Yanwei Wang & Youai Qiu, 2022. "Facile and general electrochemical deuteration of unactivated alkyl halides," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    6. Artavazd Badalyan & Shannon S. Stahl, 2016. "Cooperative electrocatalytic alcohol oxidation with electron-proton-transfer mediators," Nature, Nature, vol. 535(7612), pages 406-410, July.
    7. Jinbao Xiang & Ming Shang & Yu Kawamata & Helena Lundberg & Solomon H. Reisberg & Miao Chen & Pavel Mykhailiuk & Gregory Beutner & Michael R. Collins & Alyn Davies & Matthew Bel & Gary M. Gallego & Ji, 2019. "Hindered dialkyl ether synthesis with electrogenerated carbocations," Nature, Nature, vol. 573(7774), pages 398-402, September.
    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. Zhiwei Zhao & Ranran Zhang & Yaowen Liu & Zile Zhu & Qiuyan Wang & Youai Qiu, 2024. "Electrochemical C−H deuteration of pyridine derivatives with D2O," Nature Communications, Nature, vol. 15(1), pages 1-9, 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. Zhiwei Zhao & Ranran Zhang & Yaowen Liu & Zile Zhu & Qiuyan Wang & Youai Qiu, 2024. "Electrochemical C−H deuteration of pyridine derivatives with D2O," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    2. Liang Ge & Chi Zhang & Chengkai Pan & Ding-Xing Wang & Dong-Ying Liu & Zhi-Qiang Li & Pingkang Shen & Lifang Tian & Chao Feng, 2022. "Photoredox-catalyzed C–C bond cleavage of cyclopropanes for the formation of C(sp3)–heteroatom bonds," Nature Communications, Nature, vol. 13(1), pages 1-13, 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. Pan Ran & Aoqian Qiu & Tianshu Liu & Fangyuan Wang & Bailin Tian & Beiyao Xiang & Jun Li & Yang Lv & Mengning Ding, 2024. "Universal high-efficiency electrocatalytic olefin epoxidation via a surface-confined radical promotion," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
    5. Cong Liu & Bingbao Mei & Zhaoping Shi & Zheng Jiang & Junjie Ge & Wei Xing & Ping Song & Weilin Xu, 2024. "Operando formation of highly efficient electrocatalysts induced by heteroatom leaching," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    6. Mengjie Jiao & Jie Zhang & Minyan Wang & Hongjian Lu & Zhuangzhi Shi, 2024. "Metallaphotoredox deuteroalkylation utilizing thianthrenium salts," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    7. Meng He & Rui Li & Chuanqi Cheng & Cuibo Liu & Bin Zhang, 2024. "Microenvironment regulation breaks the Faradaic efficiency-current density trade-off for electrocatalytic deuteration using D2O," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    8. Heather A. Hintz & Christo S. Sevov, 2022. "Catalyst-controlled functionalization of carboxylic acids by electrooxidation of self-assembled carboxyl monolayers," Nature Communications, Nature, vol. 13(1), pages 1-7, December.
    9. Kaifa Du & Enlai Gao & Chunbo Zhang & Yongsong Ma & Peilin Wang & Rui Yu & Wenmiao Li & Kaiyuan Zheng & Xinhua Cheng & Diyong Tang & Bowen Deng & Huayi Yin & Dihua Wang, 2023. "An iron-base oxygen-evolution electrode for high-temperature electrolyzers," Nature Communications, Nature, vol. 14(1), pages 1-8, December.
    10. Hong Lu & Yu Zhang & Xiu-Hong Wang & Ran Zhang & Peng-Fei Xu & Hao Wei, 2024. "Carbon–nitrogen transmutation in polycyclic arenol skeletons to access N-heteroarenes," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    11. Ke Liu & Mengna Lei & Xin Li & Xuemei Zhang & Ying Zhang & Weigang Fan & Man-Bo Li & Sheng Zhang, 2024. "Paired electrocatalysis unlocks cross-dehydrogenative coupling of C(sp3)-H bonds using a pentacoordinated cobalt-salen catalyst," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    12. Qifeng Lin & Yingdong Duan & Yao Li & Ruijun Jian & Kai Yang & Zongbin Jia & Yu Xia & Long Zhang & Sanzhong Luo, 2024. "Enantioselective SN1-type reaction via electrochemically generated chiral α-Imino carbocation intermediate," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    13. Yanwei Wang & Qian Wang & Lei Wu & Kangping Jia & Minyan Wang & Youai Qiu, 2024. "Electroreduction of unactivated alkenes using water as hydrogen source," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    14. Xiangfeng Lin & Xia Mu & Hongqiang Cui & Qian Li & Zhaochi Feng & Yan Liu & Guohui Li & Can Li, 2024. "Diastereo-divergent synthesis of chiral hindered ethers via a synergistic calcium(II)/gold(I) catalyzed cascade hydration/1,4-addition reaction," Nature Communications, Nature, vol. 15(1), pages 1-13, December.
    15. Kenji Ota & Kazunori Nagao & Dai Hata & Haruki Sugiyama & Yasutomo Segawa & Ryosuke Tokunoh & Tomohiro Seki & Naoya Miyamoto & Yusuke Sasaki & Hirohisa Ohmiya, 2023. "Synthesis of tertiary alkylphosphonate oligonucleotides through light-driven radical-polar crossover reactions," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    16. Lei Fan & Xiaowan Bai & Chuan Xia & Xiao Zhang & Xunhua Zhao & Yang Xia & Zhen-Yu Wu & Yingying Lu & Yuanyue Liu & Haotian Wang, 2022. "CO2/carbonate-mediated electrochemical water oxidation to hydrogen peroxide," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    17. Chen Zhu & Huifeng Yue & Magnus Rueping, 2022. "Nickel catalyzed multicomponent stereodivergent synthesis of olefins enabled by electrochemistry, photocatalysis and photo-electrochemistry," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    18. Zhonghe Wang & Yang Tang & Songtao Liu & Liang Zhao & Huaqing Li & Cheng He & Chunying Duan, 2024. "Energy transfer-mediated multiphoton synergistic excitation for selective C(sp3)–H functionalization with coordination polymer," Nature Communications, Nature, vol. 15(1), pages 1-11, 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_s41467-023-42106-8. 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.