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Issue 6, 2014
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Preparation of functional styrenes from biosourced carboxylic acids by copper catalyzed decarboxylation in PEG

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Abstract

A general protocol for the copper-catalyzed decarboxylation of α,β-unsaturated carboxylic acids in PEG, particularly of biosourced cinnamic acid analogues, is reported. Moderate to high isolated yields (31–96%) towards the styrene derivatives were obtained. For the first time, decarboxylation of α-amino acids to the corresponding amines was successfully performed with good to high yields and extended to the decarboxylation of a few condensed heterocyclic compounds. Both the use of PEG as a green solvent and direct separation of the pure product of the reaction by distillation permitted the reuse of the solvent and the Cu-based catalytic system over several cycles without deactivation. This was extended to the synthesis of 4-vinylguaiacol on the laboratory scale in an average 92% yield.

Graphical abstract: Preparation of functional styrenes from biosourced carboxylic acids by copper catalyzed decarboxylation in PEG

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Publication details

The article was received on 14 Feb 2014, accepted on 21 Mar 2014 and first published on 21 Mar 2014


Article type: Paper
DOI: 10.1039/C4GC00256C
Citation: Green Chem., 2014,16, 3089-3097
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    Preparation of functional styrenes from biosourced carboxylic acids by copper catalyzed decarboxylation in PEG

    S. Cadot, N. Rameau, S. Mangematin, C. Pinel and L. Djakovitch, Green Chem., 2014, 16, 3089
    DOI: 10.1039/C4GC00256C

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