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https://hdl.handle.net/1822/39748
Título: | Synthesis of five-membered heterocycles by indirect electrochemical approach in "Green" media |
Autor(es): | Duraes, C. Lombard, J. Pereira, S. Esteves, Ana Paula Medeiros, Maria José |
Data: | 2015 |
Editora: | Electrochemical Society |
Revista: | Journal of The Electrochemical Society |
Citação: | Duraes, C., Lombard, J., Pereira, S., Esteves, A. P., & Medeiros, M. J. (2015). Synthesis of Five-Membered Heterocycles by Indirect Electrochemical Approach in "Green" Media. Journal of the Electrochemical Society, 162(1), G1-G7. doi: 10.1149/2.1031414jes |
Resumo(s): | Radical cyclization continues to be a central methodology for the preparation of natural products containing heterocyclic rings. Hence, some electrochemical results obtained by cyclic voltammetry and controlled-potential electrolysis in the study of electroreductive intramolecular cyclization of ethyl (2S, 3R)-2-bromo-3-propargyloxy-3-(2’,3’,4’,6’-tetra-O-acetyl-beta-D-glucopyranosyloxy) propanoate (1a), 2-bromo-3-allyloxy-3-(2’,3’,4’,6’-tetra-O-acetyl-beta-D-glucopyranosyloxy)propanoate (1b), 2-bromo-[1-(prop-2-yn-1-yloxy)propyl]benzene (1c) and [1-bromo-2-methoxy-2-(prop-2’-yn-1-yloxy)ethyl]benzene (1d) promoted by (1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecane)nickel(I), [Ni(tmc)]+, electrogenerated at glassy carbon cathodes in ethanol and ethanol:water mixtures containing tetraalkylammonium salts, are presented. During controlled-potential electrolyses of solutions containing [Ni(tmc)]2+ and bromoalkoxylated compounds (1) catalytic reduction of the latter proceeds via one-electron cleavage of the carbon–bromine bond to form a radical intermediate that undergoes cyclization to afford the substituted tetrahydrofurans. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/39748 |
DOI: | 10.1149/2.1031414jes |
ISSN: | 0013-4651 |
Arbitragem científica: | yes |
Acesso: | Acesso restrito UMinho |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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J. Electrochem. Soc., 162 (1) G1-G7 (2015).pdf Acesso restrito! | 401,54 kB | Adobe PDF | Ver/Abrir |