Why a cathodic activation by silver interface? Facile reductive homocoupling of 1-iodoalkanes

Philippe Poizot (1) , Lydia Laffont-Dantras (1) , Jacques Simonet (2)

1 LRCS - Laboratoire réactivité et chimie des solides - UMR CNRS 7314
2 ISCR - Institut des Sciences Chimiques de Rennes

Smooth silver electrodes were used for the cathodic one-electron cleavage of primary alkyl iodides, RI. It has been shown that the catalytic process making possible the reduction of RI species is based on pre-reacting alkyl iodides with silver. It is then proposed that the transient species formed (via electron transfer?) at the silver interface could be written as R-Ag+, I−. Arguments to support this proposal are presented. Such chemically modified interfaces showed a specific electrochemical behaviour in propylene carbonate (PC) in the presence of tetraalkylammonium ammonium salts. Experimental conditions for yielding specifically a one-electron step for RI species are discussed and the resulting homocoupling is evidenced.

Mots clés: Silver cathodes; Carbon-iodine bonds; Alkyl iodides; Homocoupling

Domaines: Chimie-Physique [physics.chem-ph]; Autre

Philippe Poizot, Lydia Laffont-Dantras, Jacques Simonet. Why a cathodic activation by silver interface? Facile reductive homocoupling of 1-iodoalkanes. Electrochemistry Communications, 2008, 10 (6), pp.864-867. ⟨10.1016/j.elecom.2008.03.016⟩. ⟨hal-00283485⟩