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

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, decarboxylat...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Green chemistry : an international journal and green chemistry resource : GC 2014-01, Vol.16 (6), p.3089-3097
Hauptverfasser: Cadot, Stéphane, Rameau, Nelly, Mangematin, Stéphane, Pinel, Catherine, Djakovitch, Laurent
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung: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 alpha -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.
ISSN:1463-9262
1463-9270
DOI:10.1039/c4gc00256c