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Desulfonylative Electrocarboxylation with Carbon Dioxide

  • Jun-Song Zhong
    Jun-Song Zhong
    Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou 350108, China
  • Zi-Xin Yang
    Zi-Xin Yang
    Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou 350108, China
    More by Zi-Xin Yang
  • Cheng-Lin Ding
    Cheng-Lin Ding
    Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou 350108, China
  • Ya-Feng Huang
    Ya-Feng Huang
    Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou 350108, China
  • Yi Zhao
    Yi Zhao
    BayRay Innovation Center, Shenzhen Bay Laboratory (SZBL), Guangdong 518000, China
    More by Yi Zhao
  • Hong Yan
    Hong Yan
    Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou 350108, China
    More by Hong Yan
  • , and 
  • Ke-Yin Ye*
    Ke-Yin Ye
    Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou 350108, China
    State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen 361005, P. R. China
    *Email: [email protected]
    More by Ke-Yin Ye
Cite this: J. Org. Chem. 2021, 86, 22, 16162–16170
Publication Date (Web):August 6, 2021
https://doi.org/10.1021/acs.joc.1c01261
Copyright © 2021 American Chemical Society

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    Abstract

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    Electrocarboxylation of organic halides is one of the most investigated electrochemical approaches for converting thermodynamically inert carbon dioxide (CO2) into value-added carboxylic acids. By converting organic halides into their sulfone derivatives, we have developed a highly efficient electrochemical desulfonylative carboxylation protocol. Such a strategy takes advantage of CO2 as the abundant C1 building block for the facile preparation of multifunctionalized carboxylic acids, including the nonsteroidal anti-inflammatory drug ibuprofen, under mild reaction conditions.

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    • Description of reaction setups and NMR spectra (PDF)

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    19. Benjamin R. Buckley. Electrosynthetic routes toward carbon dioxide activation and utilization. 2022, 63-93. https://doi.org/10.1016/bs.acat.2022.07.002

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