Aerobic organocatalytic photoinitiated arene oxidations: Application to electron transfer initiated cyclization reactions

Organic Letters

Volumn 3, Issue 25, 2001, Pages 4123-4125

  Kumar, V Satish ^a   Aubele, Danielle L ^a   Floreancig, Paul E ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

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ARTICLE;

EID: 0013262659     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016996f     Document Type: Article

References (27)

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19. Kumar, V. S.; Floreancig, P. E. J. Am. Chem. Soc. 2001, 123, 3842.
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22. (a) Aromatic amines are oxidized much more readily than alkylarenes. For a list of ionization potentials of organic molecules, see: Rosenstock, H. M.; Draxl, K.; Steiner, B. W.; Herron, J. T. J. Chem. Phys. Ref. Data 1997, 6, Suppl. 1. Ionization potentials can be correlated to oxidation potentials according to relationships established in ref 9b.
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25. Kopecky', J. Organic Photochemistry: A Visual Approach; VCH: New York, 1991.
26. 3 (2.0 g, 16 mmol). The mixture was irradiated at room temperature (medium-pressure mercury lamp. Pyrex filter) while air was added through a dispersion tube. After 4.5 h the mixture was filtered, washed with aqueous sodium bisulfite, and concentrated to provide 4 (584 mg, 83%).
27. 13C NMR, IR, and HRMS. See Supporting Information for details.