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Contributions of organic electrosynthesis to green chemistry

Doi : 10.1016/j.crci.2011.01.002  

Hans J. Schäfer

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Sous presse. Épreuves corrigées par l'auteur. Disponible en ligne depuis le mercredi 23 février 2011

Abstract

In organic electrosynthesis C–C bond formation and functional group interconversion proceed via reactive intermediates that are generated by electron transfer at the anode and cathode. Electron transfer combined with a chemical reaction provides conversions that are not available in non-electrochemical reactions. These are potential selectivity, redox-umpolung, and the substitution of a hydrogen atom for a nucleophile or the addition of two nucleophiles to a double bond in one-pot reactions. Furthermore electrolysis is well suited for oxidation and reduction of functional groups. Electrochemical syntheses need mostly fewer steps, produce less waste, provide a cheaper reagent, require less auxiliaries and allow often an easier scale-up than non-electrochemical syntheses. In addition, they can be conducted at ambient temperature and pressure. All these qualities agree well with the rules of green chemistry. This statement is substantiated with examples of C–C bond formation and functional group interconversion at the anode and cathode.


Keywords : Green chemistry, Organic electrosynthesis, Reactive intermediates, C–C coupling, Functional group interconversion, Umpolung, Radicals


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© 2011  Académie des sciences. Publié par Elsevier Masson SAS. Tous droits réservés.
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