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Issue 5, 2017
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Palladium-catalysed mono-α-alkenylation of ketones with alkenyl tosylates

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Abstract

The first example of palladium-catalysed selective mono-α-alkenylation of ketones with alkenyl tosylates is described. In the presence of a Pd/XPhos catalyst system (0.1–1.0 mol%), the reaction provides mono-α-alkenylated ketones in good yields and exhibits excellent substrate tolerance. Highly congested, tri- and tetra-substituted alkenyl tosylates react smoothly and even problematic heteroaryl and aliphatic ketones are applicable substrates. Notably, small β,γ-unsaturated ketones are successfully prepared using acetone as a simple three-carbon feedstock.

Graphical abstract: Palladium-catalysed mono-α-alkenylation of ketones with alkenyl tosylates

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Publication details

The article was received on 18 Oct 2016, accepted on 16 Dec 2016 and first published on 19 Dec 2016


Article type: Communication
DOI: 10.1039/C6CC08392G
Citation: Chem. Commun., 2017,53, 952-955
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    Palladium-catalysed mono-α-alkenylation of ketones with alkenyl tosylates

    Y. Wu, W. C. Fu, C. Chiang, P. Y. Choy, F. Y. Kwong and A. Lei, Chem. Commun., 2017, 53, 952
    DOI: 10.1039/C6CC08392G

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