Collect. Czech. Chem. Commun.
2003, 68, 1515-1530
https://doi.org/10.1135/cccc20031515
Electrochemical Oxidative Coupling of 4-Hydroxycinnamic Ester Derivatives: A Convenient Methodology for the Biomimetic Synthesis of Lignin Precursors
Anne Neudorffera, Brigitte Deguinb, Céline Hamela, Maurice-Bernard Fleurya and Martine Largerona,*
a Laboratoire de Chimie Analytique et Electrochimie, UMR 8638 CNRS - Université Paris 5, Faculté des Sciences Pharmaceutiques et Biologiques, 4 Avenue de l'Observatoire, 75270 Paris Cedex 06, France
b Laboratoire de Pharmacognosie, UMR 8638 CNRS - Université Paris 5, Faculté des Sciences Pharmaceutiques et Biologiques, 4 Avenue de l'Observatoire, 75270 Paris Cedex 06, France
Abstract
Based on the electrochemical oxidative coupling of 4-hydroxycinnamic ester derivatives, a straightforward biomimetic synthesis of lignin precursors is reported. This one-pot procedure leads to various naturally occurring coupling products whose distribution depends on aromatic substituents.
Keywords: Biomimetic synthesis; Dimerization; Electrochemistry; Lignans; Oxidation; Radical coupling; Cyclic voltammetry; Reaction mechanism.
References: 34 live references.
