Electrocatalytic Radical-Polar Crossover Hydroetherification of Alkenes with Phenols

Steve H. Park, Jieun Jang, Kwangmin Shin, Hyunwoo Kim

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

We disclose a general electrocatalytic hydroetherification for modular synthesis of alkyl aryl ethers by utilizing a wide range of alkenes and phenols. The integration of the two involves an electrochemically instigated cobalt-hydride-catalyzed radical-polar crossover of alkenes that enable the generation of key cationic intermediates, which could readily be entrapped by challenging nucleophilic phenols. We highlight the importance of precise control of the reaction potential by electrochemistry in conjunction with the decisive role of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as the co-solvent to obtain optimal and exclusive chemoselectivity. This reaction system is pertinent to late-stage functionalization of pharmacophores that contain alkyl aryl ethers which have constantly been challenged since traditionally unconventional methods.

Original languageEnglish
Pages (from-to)10572-10580
Number of pages9
JournalACS Catalysis
DOIs
StatePublished - 2 Sep 2022

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) [NRF-2021R1C1C1004605 (H. K.), 2021R1C1C1008190 (K. S.), and NRF-2021R1A4A3022415]. This study made use of the NMR facility supported by the Korea Basic Science Institute (National Research Facilities and Equipment Center) grant funded by the Ministry of Education (NRF-2020R1A6C101B194 and NRF-2022R1A6C101A751).

Publisher Copyright:
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Keywords

  • alkyl aryl ethers
  • cobalt hydride
  • hydroetherification
  • organic electrosynthesis
  • phenols

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