- Photocatalytic Oxidative Iodination of Electron-Rich Arenes
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A visible-light-mediated oxidative iodination of electron-rich arenes has been developed. 2.5 mol% of unsubstituted anthraquinone as photocatalyst were used in combination with elementary iodine, trifluoroacetic acid and oxygen as the terminal oxidant. The iodination proceeds upon irradiation in non- or weakly-electron donating solvents (DCM, DCE and benzene) wherein a spectral window in strongly coloured iodine solutions can be observed at around 400 nm. The method provides good to excellent yields (up to 98%) and shows excellent regioselectivity and good functional group tolerance (triple bonds, ketone, ester, amide). Moreover, the photo-iodination was also upscaled to a 5 mmol scale (1.1 g). Mechanistic investigations by intermediate trapping and competition experiments indicate a photocatalytic arene oxidation and the subsequent reaction with iodine as a likely mechanistic pathway. (Figure presented.).
- Narobe, Rok,Düsel, Simon J. S.,Iskra, Jernej,K?nig, Burkhard
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supporting information
p. 3998 - 4004
(2019/07/17)
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- An alternative to the Sandmeyer approach to aryl iodides
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Iodoarenes are important synthons for a wide range of organic transformations. Here we report a general strategy to prepare singly iodinated electron-rich aromatic compounds through the intermediacy of diaryliodonium salts. This process, which incorporates a phase separation that greatly simplifies product purification, is an attractive replacement for the Sandmeyer approach to iodoarenes that are otherwise difficult to access.
- Hu, Bao,Miller, William H.,Neumann, Kiel D.,Linstad, Ethan J.,DiMagno, Stephen G.
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supporting information
p. 6394 - 6398
(2015/04/22)
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- Progressive direct iodination of sterically hindered alkyl substituted benzenes
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Benzene derivatives bearing at least one bulky alkyl group (i-Pr or t-Bu) were selectively and effectively iodinated using elemental iodine activated, by 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor, F-TED
- Stavber, Stojan,Kralj, Petra,Zupan, Marko
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p. 1513 - 1518
(2007/10/03)
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