Aromatic Monochlorination Photosensitized by DDQ with Hydrogen Chloride under Visible-Light Irradiation

Kei Ohkubo, Atsushi Fujimoto, Shunichi Fukuzumi

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

Photochlorination of aromatic substrates by hydrogen chloride with 2,3-dichloro-5,6-cyano-p-benzoquinone (DDQ) occurs efficiently to produce the corresponding monochlorinated products selectively under visible-light irradiation. The yields for the chlorination of phenol were 70 % and 18 % for p- and o-chlorophenol, respectively, without formation of further chlorinated products. The photoinduced chlorination is initiated by electron transfer from Cl- to the triplet excited state of DDQ. The radical intermediates involved in the photochemical reaction have been detected by time-resolved transient absorption measurements.

Original languageEnglish
Pages (from-to)996-999
Number of pages4
JournalChemistry - An Asian Journal
Volume11
Issue number7
DOIs
StatePublished - 5 Apr 2016

Bibliographical note

Publisher Copyright:
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA.

Keywords

  • chlorination
  • laser flash photolysis
  • photoinduced electron transfer
  • quinone
  • radical

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