Journal
GREEN CHEMISTRY
Volume 16, Issue 6, Pages 3089-3097Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4gc00256c
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Funding
- National Agency of Research (CHEMLIVAL) [ANR-12-CDII-0001_01]
- Ministry of Research and Education
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A general protocol for the copper-catalyzed decarboxylation of alpha,beta-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 a-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.
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