Selective Oxygenation by Electron Transfer

• Ohkubo Kei

• Fukuzumi Shunichi

  Graduate School of Engineering, Osaka University, ALCA(JST)

Bibliographic Information

Other Title

• 電子移動を利用した選択的酸化反応
• デンシ イドウ オ リヨウ シタ センタクテキ サンカ ハンノウ

Abstract

Photocatalytic selective oxygenation reactions of aromatic compounds were achieved using an electron donor-acceptor linked dyad, 9-mesityl-10-methylacridinium ion (Acr⁺-Mes) as a photocatalyst and molecular oxygen as an oxidant under visible light irradiation in homogeneous conditions. The oxygenation reaction is initiated by intramolecular photoinduced electron transfer from the mesitylene moiety to the singlet excited state of acridinium moiety of Acr⁺-Mes to afford an extremely long-lived electron-transfer state. The electron-transfer state can oxidize and reduce substrates and dioxygen, respectively, leading to selective oxygenation and halogenation of substrates. Photoinduced electron transfer from benzene to the singlet excited state of 3-cyanoquinolinium ion has enabled to oxidize benzene by dioxygen to yield phenol selectively. C-C bond formation of substrates has also been made possible by using Acr⁺-Mes as a photocatalyst.

Journal

• Journal of Synthetic Organic Chemistry, Japan

  Journal of Synthetic Organic Chemistry, Japan 70 (4), 343-353, 2012

  The Society of Synthetic Organic Chemistry, Japan

Keywords

• electron transfer
• donor-acceptor linked dyads
• radical cations
• superoxide
• photocatalyst
• oxygenation

Details

• CRID: 1390282680316058624
• NII Article ID: 10030576643
• NII Book ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.70.343
• COI: 1:CAS:528:DC%2BC38XmtVOhsbg%3D
• ISSN: 18836526
• ISSN: 00379980
• NDL BIB ID: 023664807
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I023664807
• Web Site: https://www.jstage.jst.go.jp/article/yukigoseikyokaishi/70/4/70_4_343/_pdf
• Text Lang: ja
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed