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

Kei Ohkubo; Atsushi Fujimoto; Shunichi Fukuzumi

doi:10.1002/asia.201600083

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

Kei Ohkubo, Atsushi Fujimoto, Shunichi Fukuzumi

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

22 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 language	English
Pages (from-to)	996-999
Number of pages	4
Journal	Chemistry - An Asian Journal
Volume	11
Issue number	7
DOIs	https://doi.org/10.1002/asia.201600083
State	Published - 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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title = "Aromatic Monochlorination Photosensitized by DDQ with Hydrogen Chloride under Visible-Light Irradiation",

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.",

keywords = "chlorination, laser flash photolysis, photoinduced electron transfer, quinone, radical",

author = "Kei Ohkubo and Atsushi Fujimoto and Shunichi Fukuzumi",

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T1 - Aromatic Monochlorination Photosensitized by DDQ with Hydrogen Chloride under Visible-Light Irradiation

AU - Ohkubo, Kei

AU - Fujimoto, Atsushi

AU - Fukuzumi, Shunichi

PY - 2016/4/5

Y1 - 2016/4/5

N2 - 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.

AB - 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.

KW - chlorination

KW - laser flash photolysis

KW - photoinduced electron transfer

KW - quinone

KW - radical

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JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

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ER -

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

Abstract

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Keywords

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