Photocatalytic oxygenation of olefins with oxygen. Isolation of 1,2-dioxetane and the photocatalytic O-O bond cleavage

Kei Ohkubo, Takashi Nanjo, Shunichi Fukuzumi

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

Abstract

Formation of 1,2-dioxetane of tetraphenylethylene (TPE) occurs via formation of the electron transfer state of 9-mesityl-10-methylacridinium ion (Acr+-Mes) under visible light irradiation, followed by electron transfer from TPE to the Mes{radical dot}+ moiety together with electron transfer from the Acr{radical dot} moiety to O2, and the subsequent radical coupling between TPE{radical dot}+ and O2{radical dot}- to yield the corresponding 1,2-dioxetane. The dioxetane thus formed was isolated using column chromatography. Photooxygenation of stilbene derivatives is also efficiently catalyzed by Acr+-Mes, accompanied by efficient cis-trans isomerization, to afford the corresponding benzaldehydes via electron transfer from Acr{radical dot}-Mes{radical dot}+ to stilbene derivatives and oxygen.

Original languageEnglish
Pages (from-to)356-361
Number of pages6
JournalCatalysis Today
Volume117
Issue number1-3
DOIs
StatePublished - 30 Sep 2006

Bibliographical note

Funding Information:
This work was partially supported by Grants-in-Aid (Nos. 16205020 and 17750039) from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

Keywords

  • Dioxetane
  • Electron transfer
  • Olefin
  • Oxygenation
  • Radical coupling

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