NDLI: Solvent-Free One-Step Photochemical Hydroxylation of Benzene Derivatives by the Singlet Excited State of 2,3-Dichloro-5,6-dicyano-p-benzoquinone Acting as a Super Oxidant

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Solvent-Free One-Step Photochemical Hydroxylation of Benzene Derivatives by the Singlet Excited State of 2,3-Dichloro-5,6-dicyano-p-benzoquinone Acting as a Super Oxidant

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Hirose, Kensaku Ohkubo, Kei Fukuzumi, Shunichi
Description	Author Affiliation: Ohkubo K ( Department of Material and Life Science, Graduate School of Engineering, Osaka University, ALCA, JST Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7370. ookubo@chem.eng.osaka-u.ac.uk.)
Abstract	Photoinduced hydroxylation of neat deaerated benzene to phenol occurred under visible-light irradiation of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), which acts as a super photooxidant in the presence of water. Photocatalytic solvent-free hydroxylation of benzene derivatives with electron-withdrawing substituents such as benzonitrile, nitrobenzene, and trifluoromethylbenzene used as neat solvents has been achieved for the first time by using DDQ as a super photooxidant to yield the corresponding phenol derivatives and 2,3-dichloro-5,6-dicyanohydroquinone $(DDQH_{2})$ in the presence of water under deaerated conditions. In the presence of dioxygen and tert-butyl nitrite, the photocatalytic hydroxylation of neat benzene occurred with DDQ as a photocatalyst to produce phenol. The photocatalytic reactions are initiated by oxidation of benzene derivatives with the singlet and triplet excited states of DDQ to form the corresponding radical cations, which associate with benzene derivatives to produce the dimer radical cations, which were detected by the femto- and nanosecond laser flash photolysis measurements to clarify the photocatalytic reaction mechanisms. Radical cations of benzene derivatives react with water to yield the OH-adduct radicals. On the other hand, $DDQ^{.−}$ produced by the photoinduced electron transfer from benzene derivatives reacts with the OH-adduct radicals to yield the corresponding phenol derivatives and $DDQH_{2}.$ DDQ is recovered by the reaction of $DDQH_{2}$ with tert-butyl nitrite when DDQ acts as a photocatalyst for the hydroxylation of benzene derivatives by dioxygen.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	7
Volume Number	21
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2015-02-09
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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Phenol oxidation. The formation of benzofuran and 2,3-dihydrobenzofuran derivatives by oxidation of 1-(2-hydroxyphenyl)-2-(4-hydroxyphenyl)ethanes

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone as a redox titrant.

Structure, electrical conductivity and dielectric relaxation of the 1,2-bis(methylthio)benzene-2,3-dichloro-5,6-dicyano-1,4-benzoquinone 1 : 1 charge-transfer complex

SIMPLE AND SELECTIVE SPECTROPHOTOMETRIC ASSAY OF DIETHYLCARBAMAZINE CITRATE USING 2,3-DICHLORO-5,6-DICYANO-p-BENZOQUINONE AND 2,4-DINITRO PHENOL

DDQ: the chlorinating reagent and oxidant for the ligand-directed ortho-chlorination of 2-arylpyridines

Utility of p-Chloranilic Acid and 2,3-Dichloro-5,6-dicyano-p-benzoquinone for the Spectrophotometric Determination of Rizatriptan Benzoate

Solvent-Free One-Step Photochemical Hydroxylation of Benzene Derivatives by the Singlet Excited State of 2,3-Dichloro-5,6-dicyano-p-benzoquinone Acting as a Super Oxidant

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