Journal
SYNTHESIS-STUTTGART
Volume -, Issue 11, Pages 1717-1724Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2008-1067020
Keywords
alcohols; alkylations; catalysis; C-C Coupling; dicarbonyl compounds; microwave irradiation; transition metals
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A rapid and highly productive synthetic microwave-irradiation protocol for transition-metal-catalyzed carbon-carbon coupling of a wide range of benzylic/allylic alcohols with beta-diones, beta-keto esters, and dialkyl malonates is reported. In a representative screening of transition-metal catalysts, salts of Zn, Cu, Fe, Sc, Ru, Pt, Ta, and Mo were found to furnish the coupling products. In light of the results obtained, among all of these catalysts copper(II) triflate was found to be relatively more effective compared to other catalysts even in the case of a less reactive benzyl alcohol or diester. Interestingly, these MW-irradiated reactions are performed in a more or less MW-transparent medium, such as toluene, having a very low tan delta, or under neat conditions.
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