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Microwave Irradiation as a Green Alternative to Phase Transfer Catalysis: Solid-Liquid Phase Alkylation of Active Methylene Containing Substrates Under Solvent-Free Conditions

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An ecofriendly, microwave (MW) promoted and solventless method is described for the alkylation of diethyl malonate, ethyl acetoacetate and ethyl cyanoacetate by a variety of alkyl halides in the presence of K2CO3. In the solidliquid phase alkylation of active methylene containing substrates, it seems to be of general value that the phase-transfer catalyst, that is an onium salt in the present case, can be omitted and substituted by MW irradiation promoting the formation of the potassium salt of the substrate and its transfer to the organic phase. In certain cases, the use of triethylbenzylammonium chloride led to the formation of by-products under the conditions (∼160 ° C/∼12 bar) applied.

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Keywords: C-alkylation; Microwave synthesis; green-chemistry; phase-transfer catalysis; solvent-free reaction

Document Type: Research Article

Publication date: 2008-04-01

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  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
    The journal is essential reading for all organic chemists both in academia and industry.
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