View : 856 Download: 0
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, Kei; Hirose, Kensaku; Fukuzumi, Shunichi
- Ewha Authors
- Shunichi Fukuzumi; Kei Okubo
- SCOPUS Author ID
- Shunichi Fukuzumi; Kei Okubo
- Issue Date
- 2016
- Journal Title
- CHEMISTRY-AN ASIAN JOURNAL
- ISSN
- 1861-4728
1861-471X
- Citation
- CHEMISTRY-AN ASIAN JOURNAL vol. 11, no. 16, pp. 2255 - 2259
- Keywords
- electron transfer; oxygenation; photoredox catalysis; quinone; radical
- Publisher
- WILEY-V C H VERLAG GMBH
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- 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
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
- Files in This Item:
There are no files associated with this item.
- Export
- RIS (EndNote)
- XLS (Excel)
- XML