Collect. Czech. Chem. Commun. 2000, 65, 844-861

Electrochemical Reduction of Allyl Ethers in the Presence of Nickel Complexes: A Review of Synthetic Applications

Sandra Oliveroa, Delphine Francoa, Jean-Claude Clinetb and Elisabet Duñacha,*

a Laboratoire de Chimie Bio-organique, associé au CNRS, Université de Nice-Sophia Antipolis, 06108 Nice cedex 2, France
b Institut de Chimie Moléculaire, associé au CNRS, Université Paris-Sud, 95405 Orsay, France


This review deals with the electrochemical reactivity of a family of organic compounds, namely allyl ether derivatives, in the presence of various catalytic systems. Essentially, nickel complexes associated with various ligands have been described for such reactions. The electrochemical reduction of allyl aryl ethers has been reported to be very dependent on the nature of the catalytic system. Ni(II) complexes with 2,2'-bipyridine ligands selectively catalyze the cleavage of the O-C(allyl) bond to afford the corresponding alcohol or phenol derivatives in good yields. The related ortho-halogenated allyl ether substrates, in the presence of Ni(II) catalysts with cyclam-type macrocyclic ligands undergo intramolecular cyclizations. The nature of the ligand on nickel strongly influences the reactivity and the chemoselectivity of these processes. A review with 62 references.

Keywords: Electrochemical reductions; Nickel; Allyl ethers; Cleavage; Cyclization; Protecting groups; Bipyridine ligands.

References: 82 live references.