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Solvent-Free Photooxidation of Alkanes by Dioxygen with 2,3-Dichloro-5,6-dicyano-p-benzoquinone via Photoinduced Electron Transfer

Title
Solvent-Free Photooxidation of Alkanes by Dioxygen with 2,3-Dichloro-5,6-dicyano-p-benzoquinone via Photoinduced Electron Transfer
Authors
Ohkubo, KeiHirose, KensakuFukuzumi, Shunichi
Ewha Authors
Shunichi FukuzumiKei Okubo
SCOPUS Author ID
Shunichi Fukuzumiscopus; Kei Okuboscopus
Issue Date
2016
Journal Title
CHEMISTRY-AN ASIAN JOURNAL
ISSN
1861-4728JCR Link1861-471XJCR Link
Citation
vol. 11, no. 16, pp. 2255 - 2259
Keywords
electron transferoxygenationphotoredox catalysisquinoneradical
Publisher
WILEY-V C H VERLAG GMBH
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
Photooxidation of alkanes by dioxygen occurred under visible light irradiation of 2,3-dichloro-5,6-dicyanop-benzoquinone (DDQ) which acts as a super photooxidant. Solvent-free hydroxylation of cyclohexane and alkanes is initiated by electron transfer from alkanes to the singlet and triplet excited states of DDQ to afford the corresponding radical cations and DDQ(center dot-), as revealed by femtosecond laser-induced transient absorption measurements. Alkane radical cations readily deprotonate to produce alkyl radicals, which react with dioxygen to afford alkylperoxyl radicals. Alkylperoxyl radicals abstract hydrogen atoms from alkanes to yield alkyl hydroperoxides, accompanied by regeneration of alkyl radicals to constitute the radical chain reactions, so called autoxidation. The radical chain is terminated in the bimolecular reactions of alkylperoxyl radicals to yield the corresponding alcohols and ketones. DDQ(center dot-), produced by the photoinduced electron transfer from alkanes to the excited state of DDQ, disproportionates with protons to yield DDQH(2).
DOI
10.1002/asia.201600828
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자연과학대학 > 화학·나노과학전공 > Journal papers
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