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- W2952264492 abstract "The stannane-mediated benzeneselenol-catalyzed addition of aryl iodides to a range of arenes and aromatic hetereocycles has been studied. With furan, thiophene, and several carbocyclic arenes, the addition takes place with quenching of the adduct radical by the catalytic selenol leading to moderate yields of aryl-dihydroarenes. With nitrogen heterocycles, on the other hand, it was not possible to suppress aromatization of the adduct radical and fully aromatized products were isolated. Aryl iodides bearing hydrogen bond donating groups in the ortho-position add to nitrogen heterocycles with high selectivity ortho- to the nitrogen, affording a simple one-step synthesis of potential chelating ligands. While 2-iodophenol is an excellent aryl radical source in these reactions, the homologous 1-iodo-2-naphthol fails owing to its reaction with diphenyl diselenide, which gives 1-phenylseleno-2-naphthol in high yield." @default.
- W2952264492 created "2019-06-27" @default.
- W2952264492 creator A5027175360 @default.
- W2952264492 creator A5067703231 @default.
- W2952264492 date "2006-08-01" @default.
- W2952264492 modified "2023-10-16" @default.
- W2952264492 title "Radical dearomatization of arenes and heteroarenes" @default.
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- W2952264492 doi "https://doi.org/10.1016/j.tet.2006.05.051" @default.
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