ChemElectroChem (May 2024)

Electrochemical C(sp3)−H Functionalization Using Acetic Acid as a Hydrogen Atom Transfer Reagent

  • Yuma Morii,
  • Taito Watanabe,
  • Dr. Yutaka Saga,
  • Prof. Dr. Tetsuya Kambe,
  • Prof. Dr. Mio Kondo,
  • Prof. Dr. Shigeyuki Masaoka

DOI
https://doi.org/10.1002/celc.202400061
Journal volume & issue
Vol. 11, no. 10
pp. n/a – n/a

Abstract

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Abstract In this study, we developed a novel electrochemical protocol that enables the functionalization of inherently inert C(sp3)−H bonds. In this protocol, one‐electron oxidation of acetic acid was used to successfully generate methyl radical, which cleaves the benzylic C(sp3)−H bonds of the substrates via a hydrogen atom transfer (HAT) process, and further reaction with the formed species yields the targeted C(sp3)−H functionalized products. To the best of our knowledge, this is the first example of the use of acetic acid in a HAT process. Notably the reaction has environment‐friendly and fine atom economy nature: the reaction is driven by the electrochemical conditions in the absence of expensive or hazardous reagents, producing only gaseous small molecules, hydrogen, carbon dioxide, and methane, as side products.

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