Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 8, Issue 18, Pages 4158-4164Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0ob00066c
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- Murst, Rome
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Benzoyl radicals are generated directly from (hetero)aromatic aldehydes upon tetrabutylammonium decatungstate ((n-Bu(4)N)(4)W(10)O(32)), TBADT) photocatalysis under mild conditions. In the presence of alpha,beta-unsaturated esters, ketones and nitriles radical conjugate addition ensues and gives the corresponding beta-functionalized aryl alkyl ketones in moderate to good yields (stereoselectively in the case of 3-methylene-2-norbornanone). Due to the mild reaction conditions the presence of various functional groups on the aromatic ring is tolerated (e. g. methyl, methoxy, chloro). The method can be applied to hetero-aromatic aldehydes whether electron-rich (e. g. thiophene-2-carbaldehyde) or electron-poor (e. g. pyridine-3-carbaldehyde).
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