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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
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    References listed on IDEAS

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    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. Artavazd Badalyan & Shannon S. Stahl, 2016. "Cooperative electrocatalytic alcohol oxidation with electron-proton-transfer mediators," Nature, Nature, vol. 535(7612), pages 406-410, July.
    5. 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.
    6. 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.
    7. 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.
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    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.

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