Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 14-15, Pages 2891-2899Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300598
Keywords
benzylation; CH bond activation; photocatalysis; polyoxometalates; radicals
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Funding
- Italian Ministry of Foreign Affairs through the E-PLUS project (Enhancement of the Palestinian University System)
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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.
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