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Synfacts 2010(10): 1177-1177  
DOI: 10.1055/s-0030-1258079
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Decarboxylative Benzylation of Alkynes and Substituted Ketones

Contributor(s): Paul Knochel, Tobias Thaler
R. R. P. Torregrosa, Y. Ariyarathna, K. Chattopadhyay, J. A. Tunge*
University of Kansas, Lawrence, USA
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Publication History

Publication Date:
22 September 2010 (online)

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Significance

The benzyl esters of propiolic and β-keto acids were shown to undergo a decarboxylative coupling under palladium catalysis. Remarkably, this method does not only allow C-C bond formations leading to quaternary all-carbon centers, but also the construction of 1,4-ketone analogues that cannot be accessed via common base-mediated enolate reactions.