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Ritter-type amination of C(sp3)-H bonds enabled by electrochemistry with SO42−

Author

Listed:
  • Ling Zhang

    (East China University of Science and Technology)

  • Youtian Fu

    (East China University of Science and Technology)

  • Yi Shen

    (East China University of Science and Technology)

  • Chengyu Liu

    (East China University of Science and Technology)

  • Maolin Sun

    (Guangdong University of Technology)

  • Ruihua Cheng

    (Guangdong University of Technology)

  • Weiping Zhu

    (East China University of Science and Technology)

  • Xuhong Qian

    (East China University of Science and Technology)

  • Yueyue Ma

    (Guangdong University of Technology)

  • Jinxing Ye

    (East China University of Science and Technology
    Guangdong University of Technology)

Abstract

By merging electricity with sulfate, the Ritter-type amination of C(sp3)-H bonds is developed in an undivided cell under room temperature. This method features broad substrate generality (71 examples, up to 93% yields), high functional-group compatibility, facile scalability, excellent site-selectivity and mild conditions. Common alkanes and electron-deficient alkylbenzenes are viable substrates. It also provides a straightforward protocol for incorporating C-deuterated acetylamino group into C(sp3)-H sites. Application in the synthesis or modification of pharmaceuticals or their derivatives and gram-scale synthesis demonstrate the practicability of this method. Mechanistic experiments show that sulfate radical anion, formed by electrolysis of sulfate, served as hydrogen atom transfer agent to provide alkyl radical intermediate. This method paves a convenient and flexible pathway for realizing various synthetically useful transformations of C(sp3)-H bonds mediated by sulfate radical anion generated via electrochemistry.

Suggested Citation

  • Ling Zhang & Youtian Fu & Yi Shen & Chengyu Liu & Maolin Sun & Ruihua Cheng & Weiping Zhu & Xuhong Qian & Yueyue Ma & Jinxing Ye, 2022. "Ritter-type amination of C(sp3)-H bonds enabled by electrochemistry with SO42−," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-31813-3
    DOI: 10.1038/s41467-022-31813-3
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