Facile aerobic photooxidation of methyl group in the aromatic nucleus in the presence of an organocatalyst under VIS irradiation

Green Chemistry

Volumn 13, Issue 7, 2011, Pages 1669-1671

  Tada, Norihiro ^a   Hattori, Kasumi ^a   Nobuta, Tomoya ^a   Miura, Tsuyoshi ^a   Itoh, Akichika ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

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Indexed keywords

EID: 79960262116     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c1gc15154a     Document Type: Article

References (28)

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19. The yield of the product decreases when going down in AQN concentration. In our examination, 8 mol% of the catalyst was found to produce the product in high yield constantly.
20. See Tables S1–S4 in the ESI.
21. See Table S5 in the ESI.
22. S. Hirashima T. Nobuta N. Tada T. Miura A. Itoh Org. Lett. 2010 12 3645.
23. See Fig. 1–3 in the ESI.
24. We also detected the formation of molecular oxygen when the reaction mixture made contact with catalase. See the ESI regarding the measurement of peroxide by iodometry.
25. 2-Chloroanthraquinone absorbs light with wavelengths shorter than 450 nm, and the fluorescent lamp radiates visible light with wavelengths longer than 400 nm. Thus, 2-chloroanthraquinone absorbs light between 400 and 450 nm.
26. The aldehyde 7 is also thought to be formed through Russell termination path from peroxyradical 5. Russell termination leads to a mixture of aldehyde and alcohol. And the alcohol will be oxidized in the system rapidly.
27. We have never examined the stability of organo photocatalyst. There is a possibility that peroxide adducts of AQN exist in solution since we detected the compound derived from AQN by NMR; however, we could not determine the detailed structure.
28. Acetone and acetonitrile easily form the solvent-HOOH adducts, and produce benzoylperoxide; however, we do not think this is applicable to our protocol with EtOAc as solvent.