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Efficient Palladium-Catalyzed Cross-Coupling of β-Chloroalkylidene/arylidene Malonates Using Microwave Chemistry

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School of Chemistry, University of Edinburgh, King's Buildings, West Mains Road, Edinburgh EH9 3JJ, U.K., and Cyclacel Ltd., James Lindsay Place, Dundee DD1 5JJ, U.K. [email protected]
Cite this: J. Org. Chem. 2004, 69, 20, 6920–6922
Publication Date (Web):September 2, 2004
https://doi.org/10.1021/jo049132r
Copyright © 2004 American Chemical Society
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    Abstract

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    A general method for the synthesis of β-aryl/alkylarylidene malonates is reported. The key step involves the coupling of an arylboronic acid to a β-chloroalkyl/arylidene malonate, in the presence of K2CO3 and 1 mol % of the air-stable palladium catalyst (POPd) under microwave irradiation, to afford β-aryl/alkylarylidene malonates in good yields. The combination of mild reaction conditions, air stable catalyst, microwave-enhanced chemistry, and high levels of functional group compatibility make this an attractive synthetic approach to this class of compounds.

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    †

     University of Edinburgh School of Chemistry.

    ‡

     Cyclacel Ltd.

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    Experimental details and spectral data for all transformations and compounds described. This material is available free of charge via the Internet at http://pubs.acs.org.

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