Organic cyclisations of propargyl and allyl bromoesters in microemulsions catalysed by electrogenerated nickel(I) tetramethylcyclam

abstract

While the reductive intramolecular cyclisation of propargyl and allyl bromoesters catalysed by [Ni(tmc)](+) gives good yields of the desired products using NN-dimethylformamide as the solvent, the use of this aprotic solvent presents practical, safety and environmental issues. This paper therefore reports the search for non-toxic alternatives, in particular the study of microemulsions prepared from water, hydrocarbons, surfactant and alcohol co-surfactant. It is shown that the [Ni(tmc)](2+)/[Ni(tmc)](+) couple is reversible in such media and that [Ni(tmc)](+) reacts rapidly with propargyl and allyl bromoesters to give excellent yields of cyclic products. Indeed, these microemulsions are convenient media for such syntheses. (c) 2007 Elsevier B.V. All rights reserved.

keywords

ELECTROREDUCTIVE RADICAL CYCLIZATION; VITREOUS CARBON CATHODES; INTRAMOLECULAR CYCLIZATION; BICONTINUOUS MICROEMULSION; ELECTROCHEMICAL REDUCTION; ALKYL BROMIDES; UNSATURATED HALIDES; TETRAAZA MACROCYCLE; COMPLEXES; DIMETHYLFORMAMIDE

subject category

Chemistry; Electrochemistry

authors

Esteves, AP; Neves, CS; Medeiros, MJ; Pletcher, D

our authors

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