Metal Cations from Sacrificial Anodes Act as a Lewis Acid Co-Catalyst in Electrochemical Cross-Coupling of Aryl Bromides and Aziridines

Gadde Sathish Kumar, Chen Zhu, Rajesh Kancherla, Prashant S. Shinde, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

An efficient method for the reductive cross-electrophile coupling of aziridines with aryl halides using nickel electrocatalysis is reported. This reaction provides valuable phenethylamines at room temperature in good yields. The reaction was successfully applied to the electro-reductive cross-coupling of less reactive, unsubstituted N-tosylaziridine. Additionally, we were even able to couple challenging alkyl bromides with aryl aziridines. Control experiments and voltammetric studies confirm that the mechanism is distinct from conventional and photochemical couplings. Furthermore, the role of both Ni(II) organometallic complexes and electrodes was examined, providing insight into the reaction mechanism and the beneficial role of the sacrificial anode in electrochemical cross-couplings.

Original languageEnglish (US)
Pages (from-to)8813-8820
Number of pages8
JournalACS Catalysis
Volume13
Issue number13
DOIs
StatePublished - Jul 7 2023

Bibliographical note

Funding Information:
This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/4405). The authors acknowledge KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II.

Publisher Copyright:
© 2023 American Chemical Society

Keywords

  • aziridine
  • cross-coupling
  • electrochemical
  • iron
  • Lewis acid
  • nickel

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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