Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 12, Issue 32, Pages 6059-6071Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob00843j
Keywords
-
Categories
Funding
- ALCA fund from Japan Science and Technology Agency (JST)
- Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan
- Grants-in-Aid for Scientific Research [26288037, 26620154] Funding Source: KAKEN
Ask authors/readers for more resources
The oxidizing ability of organic dyes is enhanced significantly by photoexcitation. Radical cations of weak electron donors can be produced by electron transfer from the donors to the excited states of organic dyes. The radical cations thus produced undergo bond formation reactions with various nucleophites. For example, the direct oxygenation of benzene to phenol was made possible under visible-light irradiation of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) in an oxygen-saturated acetonitrile solution of benzene and water via electron transfer from benzene to the triplet excited state of DDQ. 3-Cyano-1-methylquinolinium ion (QuCN(+)) can also act as an efficient photocatalyst for the selective oxygenation of benzene to phenol using oxygen and water under homogeneous and ambient conditions. Alkoxybenzenes were also obtained when water was replaced by alcohol under otherwise identical experimental conditions. QuCN+ can also be an effective photocatalyst for the fluorination of benzene with O-2 and fluoride anion. Photocatalytic selective oxygenation of aromatic compounds was achieved using an electron donor-acceptor-linked dyad, 9-mesityl-10-methylacridinium ion (Acr(+)-Mes), as a photocatalyst and O-2 as the oxidant under visible-light irradiation. The electron-transfer state of Acr(+)-Mes produced upon photoexcitation can oxidize and reduce substrates and dioxygen, respectively, leading to the selective oxygenation and halogenation of substrates. Acr(+)-Mes has been utilized as an efficient organic photoredox catalyst for many other synthetic transformations.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available