Electroreductive intramolecular cyclisation of bromoalkoxylated derivatives catalysed by nickel(I) tetramethylcyclam in "green" media
authors Medeiros, MJ; Neves, CSS; Pereira, AR; Dunach, E
nationality International
journal ELECTROCHIMICA ACTA
author keywords Microemulsions; Electrosynthesis; Catalytic reduction; Intramolecular cyclisation; Nickel(II) complex
keywords CARBON BOND FORMATION; RADICAL CYCLIZATION; ALKYL-HALIDES; MICROEMULSION STRUCTURE; ELECTROCHEMICAL REDUCTION; TETRAAZA MACROCYCLE; COMPLEXES; DIMETHYLFORMAMIDE; CATHODES; BROMIDES
abstract The (1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetra-decane)nickel(I), [Ni(tmc)](+), electrogenerated at glassy carbon cathodes is shown to be an effective catalyst for the intramolecular radical-type cyclisation of bromoalkoxylated derivatives 1 in alcohol and/or alcohol/water mixtures as well as in microemulsions made with cationic and anionic surfactants. The results obtained indicate that the reaction proceeds via cleavage of the carbon-bromine bond to form a radical-type intermediate that undergoes cyclisation on the unsaturated C-C bond to afford substituted tetrahydrofurans. The reactions are more selective and take place at higher current density than when carried out in conventional aprotic solvents. (c) 2011 Elsevier Ltd. All rights reserved.
publisher PERGAMON-ELSEVIER SCIENCE LTD
issn 0013-4686
year published 2011
volume 56
issue 12
beginning page 4498
ending page 4503
digital object identifier (doi) 10.1016/j.electacta.2011.02.054
web of science category Electrochemistry
subject category Electrochemistry
unique article identifier WOS:000290701500011
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