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Decatungstate photocatalyzed benzylation of alkenes by alkylaromatics

Authors: 
Hisham Qrareya, Davide Ravelli, Maurizio Fagnoni, and Angelo Albini.
Journal Name: 
Adv. Synth. Catal.
Volume: 
1
Issue: 
355
Pages From: 
2891
To: 
2899
Date: 
Monday, September 9, 2013
Keywords: 
benzylation; CH bond activation; photocatalysis; polyoxometalates; radicals
Project: 
the Italian Ministry of Foreign Affairs through the E-PLUS project (Enhancement of the Palestinian University System).
Abstract: 
The direct benzylation of electrophilic alkenes with alkylbenzenes has been achieved by decatungstate photocatalysis in a high ionic strength medium (5:1 acetonitrile/water mixed solvents, 0.5M lithium perchlorate). The reaction has been extended to ring-substituted (Cl, F, CN) toluenes and further alkylbenzenes. Intramolecular selectivity (p-cymene, 4-methylanisole) and deuteration effects support the atom transfer character of the process that, however, requires a sufficient stabilization of the intermediate polar exciplex to occur. The reactivity of the decatungstate anion is compared with that of aromatic ketones, the benchmark of photochemical hydrogen/ electron transfer processes.