Electrosynthesis of nitrogen heterocycles using environmentally friendly methodologies

abstract

Cyclic voltammetry and constant-current electrolysis in a one-compartment cell with a sacrificial anode has been used to study the indirect electroreduction of N-allyl-alpha-haloamides by electrogenerated Ni(1) complexes conducted in N,N-dimethylformantide (DMF) and acetonitrile (ACN) and the results were compared with those obtained in protic solvents such as EtOH and EtOH-H(2)O mixtures. It was observed that the indirect electrochemical reduction of N-allyl-alpha-haloamides led to the corresponding lactams and the yields and selectivities obtained in EtOH and EtOH-H(2)O were much better than those obtained in DMF or ACN. (C) 2009 Elsevier Ltd. All rights reserved.

keywords

INDIRECT ELECTROREDUCTIVE CYCLIZATION; RADICAL CYCLIZATION; INTRAMOLECULAR CYCLIZATION; NICKEL(I) MACROCYCLE; UNSATURATED HALIDES; TETRAAZA MACROCYCLE; CARBON CATHODES; ORGANIC HALIDES; ALKYL-HALIDES; COMPLEXES

subject category

Electrochemistry

authors

Chaminade, X; Dunach, E; Esteves, AP; Medeiros, MJ; Neves, CS; Olivero, S

our authors

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