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Issue 13, 2015
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Olefins from biomass feedstocks: catalytic ester decarbonylation and tandem Heck-type coupling

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Abstract

With the goal of avoiding the need for anhydride additives, the catalytic decarbonylation of p-nitrophenylesters of aliphatic carboxylic acids to their corresponding olefins, including commodity monomers like styrene and acrylates, has been developed. The reaction is catalyzed by palladium complexes in the absence of added ligands and is promoted by alkali/alkaline-earth metal halides. Combination of catalytic decarbonylation and Heck-type coupling with aryl esters in a single pot process demonstrates the viability of employing a carboxylic acid as a “masked olefin” in synthetic processes.

Graphical abstract: Olefins from biomass feedstocks: catalytic ester decarbonylation and tandem Heck-type coupling

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Publication details

The article was received on 11 Nov 2014, accepted on 03 Jan 2015 and first published on 12 Jan 2015


Article type: Communication
DOI: 10.1039/C4CC09003A
Citation: Chem. Commun., 2015,51, 2731-2733
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    Olefins from biomass feedstocks: catalytic ester decarbonylation and tandem Heck-type coupling

    A. John, L. T. Hogan, M. A. Hillmyer and W. B. Tolman, Chem. Commun., 2015, 51, 2731
    DOI: 10.1039/C4CC09003A

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