Issue 18, 2010

Benzoyl radicals from (hetero)aromatic aldehydes. Decatungstate photocatalyzed synthesis of substituted aromatic ketones

Abstract

Benzoyl radicals are generated directly from (hetero)aromatic aldehydes upon tetrabutylammonium decatungstate ((n-Bu4N)4W10O32), TBADT) photocatalysis under mild conditions. In the presence of α,β-unsaturated esters, ketones and nitriles radical conjugate addition ensues and gives the corresponding β-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).

Graphical abstract: Benzoyl radicals from (hetero)aromatic aldehydes. Decatungstate photocatalyzed synthesis of substituted aromatic ketones

Supplementary files

Article information

Article type
Paper
Submitted
30 Apr 2010
Accepted
16 Jun 2010
First published
27 Jul 2010

Org. Biomol. Chem., 2010,8, 4158-4164

Benzoyl radicals from (hetero)aromatic aldehydes. Decatungstate photocatalyzed synthesis of substituted aromatic ketones

D. Ravelli, M. Zema, M. Mella, M. Fagnoni and A. Albini, Org. Biomol. Chem., 2010, 8, 4158 DOI: 10.1039/C0OB00066C

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