Efficient photocatalytic oxygenation of toluene occurs under visible light irradiation of 9-mesityl-10-methylacridinium (Acr+–Mes) in oxygen-saturated acetonitrile containing toluene and aqueous hydrochloric acid with a xenon lamp for 15 h. The oxygenated products, benzoic acid (70 %) and benzaldehyde (30 %), were formed after the photoirradiation. The photocatalytic reaction is initiated by intramolecular photoinduced electron transfer from the mesitylene moiety to the singlet excited state of the Acr+ moiety of Acr+–Mes, which affords the electron-transfer state, Acr•–Mes•+. The Mes•+ moiety can oxidize chloride ion (Cl−) by electron transfer to produce chlorine radical (Cl•), whereas the Acr• moiety can reduce O2 to O 2 •− . The Cl• radical produced abstracts a hydrogen from toluene to afford benzyl radical in competition with the bimolecular radical coupling of Cl•. The benzyl radical reacts with O2 rapidly to afford the peroxyl radical, leading to the oxygenated product, benzaldehyde. Benzaldehyde is readily further photooxygenated to yield benzoic acid with Acr•–Mes•+. In the case of an aromatic compound with electron-donating substituents, 1,3,5-trimethoxybenzene, photocatalytic chlorination occurred efficiently under the same photoirradiation conditions to yield a monochloro-substituted compound, 2,4,6-trimethoxychlorobenzene.
Research on Chemical Intermediates – Springer Journals
Published: Jun 21, 2012
It’s your single place to instantly
discover and read the research
that matters to you.
Enjoy affordable access to
over 18 million articles from more than
15,000 peer-reviewed journals.
All for just $49/month
Query the DeepDyve database, plus search all of PubMed and Google Scholar seamlessly
Save any article or search result from DeepDyve, PubMed, and Google Scholar... all in one place.
Get unlimited, online access to over 18 million full-text articles from more than 15,000 scientific journals.
Read from thousands of the leading scholarly journals from SpringerNature, Elsevier, Wiley-Blackwell, Oxford University Press and more.
All the latest content is available, no embargo periods.
“Hi guys, I cannot tell you how much I love this resource. Incredible. I really believe you've hit the nail on the head with this site in regards to solving the research-purchase issue.”Daniel C.
“Whoa! It’s like Spotify but for academic articles.”@Phil_Robichaud
“I must say, @deepdyve is a fabulous solution to the independent researcher's problem of #access to #information.”@deepthiw
“My last article couldn't be possible without the platform @deepdyve that makes journal papers cheaper.”@JoseServera