Towards a facile synthesis of triarylethanones: palladium-catalyzed arylation of ketone enolates under homogeneous and heterogeneous conditions

The palladium-catalyzed regioselective α-monoarylation of deoxybenzoins and α,α-diarylation of acetophenones provides general, efficient access to 1,2,2-triarylethanones. After a comprehensive search for suitable experimental conditions to optimize such transformations, both reactions are alternativ...

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Bibliographic Details
Published in:Tetrahedron 2004-03, Vol.60 (10), p.2393-2408
Main Authors: Churruca, Fátima, SanMartin, Raul, Carril, Mónica, Tellitu, Imanol, Domı́nguez, Esther
Format: Article
Language:English
Subjects:
Arylation
Ketones
Palladium and compounds
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Summary:The palladium-catalyzed regioselective α-monoarylation of deoxybenzoins and α,α-diarylation of acetophenones provides general, efficient access to 1,2,2-triarylethanones. After a comprehensive search for suitable experimental conditions to optimize such transformations, both reactions are alternatively conducted by means of either commercially available polymer-anchored catalysts or a very simple homogeneous catalytic system, thus avoiding the use of complex ligands. In addition, the synthesis of deoxybenzoins employing polymer-supported fibrous palladium catalysts is reported for the first time, and the excellent catalyst recycling properties suggest applicability to industrial purposes. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2003.12.065