Electro-reductive cyclization of aryl halides promoted by fluorene derivatives

Koichi Mitsudo, Yumiko Nakagawa, Jun Ichi Mizukawa, Hideo Tanaka, Ryoichi Akaba, Takahiro Okada, Seiji Suga

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

In the presence of fluorene derivatives, the electro-reduction of aryl chlorides, bromides, and iodides bearing an ethylene moiety proceeded smoothly to afford the corresponding cyclized products. Noteworthy is that aryl chlorides, which have more negative reduction potential than aryl bromides and iodides, exhibited high reactivity in the reaction, and the corresponding five-membered and six-membered cyclized products were obtained in good to high yields. Mechanistic study suggests that the electro-reduction of fluorene derivatives was essential for the reactions, indicating that they work as a mediator.

Original languageEnglish
Pages (from-to)444-449
Number of pages6
JournalElectrochimica Acta
Volume82
DOIs
Publication statusPublished - Nov 1 2012

Keywords

  • Electro-reduction
  • Fluorene
  • Mediator
  • Radical cyclization
  • Reductive cyclization

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Electrochemistry

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