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Ohkubo, Kei,Mizushima, Kentaro,Iwata, Ryosuke,Souma, Kazunori,Suzuki, Nobuo,Fukuzumi, Shunichi Royal Society of Chemistry 2010 Chemical communications Vol.46 No.4
<P>Photooxygenation of <I>p</I>-xylene by oxygen occurs efficiently under photoirradiation of 9-mesityl-2,7,10-trimethylacridinium ion (Me<SUB>2</SUB>Acr<SUP>+</SUP>–Mes) to yield <I>p</I>-tolualdehyde and hydrogen peroxide, which is initiated <I>via</I> photoinduced electron transfer of Me<SUB>2</SUB>Acr<SUP>+</SUP>–Mes to produce the electron-transfer state.</P> <P>Graphic Abstract</P><P>Photooxygenation of <I>p</I>-xylene by oxygen occurs efficiently under photoirradiation of mesitylacridinium in an O<SUB>2</SUB>-saturated acetonitrile solution to yield <I>p</I>-tolualdehyde and hydrogen peroxide. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=b920606j'> </P>
Ohkubo, Kei,Mizushima, Kentaro,Iwata, Ryosuke,Fukuzumi, Shunichi Royal Society of Chemistry 2011 Chemical Science Vol.2 No.4
<P>Photocatalytic bromination of aromatic hydrocarbons by molecular oxygen with hydrogen bromide occurs efficiently to produce monobrominated products selectively using 9-mesityl-10-methylacridinium ion (Acr<SUP>+</SUP>–Mes) as a photocatalyst under visible light irradiation. Both the product yield and selectivity for the bromination of 1,3,5-trimethoxybenzene were 100% with a quantum yield of 4.8%. The photocatalytic turnover number is 900 based on the initial concentration of Acr<SUP>+</SUP>–Mes. The reactive radical intermediates involved in the photocatalytic cycle have been successfully detected by laser flash photolysis measurements. The photocatalytic bromination is initiated by photoinduced electron transfer from the mesitylene moiety to the singlet excited state of acridinium ion, which results in formation of the electron-transfer state of Acr<SUP>+</SUP>–Mes (Acr˙–Mes˙<SUP>+</SUP>), followed by electron transfer from aromatic hydrocarbons to the mesitylene radical cation moiety and electron transfer from the acridinyl radical moiety to O<SUB>2</SUB>. The resulting radical cations of aromatic hydrocarbons react with Br<SUP>−</SUP> to produce the corresponding monobrominated products selectively.</P> <P>Graphic Abstract</P><P>Photocatalytic bromination of aromatic hydrocarbons by O<SUB>2</SUB> with HBr occurs efficiently to produce the monobrominated products using 9-mesityl-10-methylacridinium ion. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c0sc00535e'> </P>