Selective radical cyclisation of propargyl bromoethers to tetrahydrofuran derivatives via electrogenerated nickel(I) tetramethylcyclam

The controlled-potential reduction of [1-bromo-2-methoxy-2-(prop-2′-ynyloxy)ethyl]benzene ( 1a), 1-[2-bromo-2-phenyl-1-(prop-2′-ynyloxy)ethyl]-4-methoxybenzene ( 1b) and 2-bromo-3-(3′,4′-dimethoxyphenyl)-3-propargyloxypropanamide ( 1c) catalysed by (1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetrade...

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Bibliographic Details
Published inTetrahedron Vol. 63; no. 14; pp. 3006 - 3009
Main Authors Esteves, A.P., Ferreira, E.C., Medeiros, M.J.
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 02.04.2007
Subjects
Electrocatalytic reduction
Electrosynthesis
Intramolecular cyclisation
Nickel(I) tetramethylcyclam
Electrosynthesis
Intramolecular cyclisation
Electrocatalytic reduction
Nickel(I) tetramethylcyclam
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Summary:The controlled-potential reduction of [1-bromo-2-methoxy-2-(prop-2′-ynyloxy)ethyl]benzene ( 1a), 1-[2-bromo-2-phenyl-1-(prop-2′-ynyloxy)ethyl]-4-methoxybenzene ( 1b) and 2-bromo-3-(3′,4′-dimethoxyphenyl)-3-propargyloxypropanamide ( 1c) catalysed by (1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecane)nickel(I), [Ni(tmc)] +, at a vitreous carbon cathode in DMF/Et 4NBF 4 leads to 2-methoxy-4-methylene-3-phenyl-tetrahydrofuran ( 2a), 2-(4′-methoxyphenyl)-4-methylene-3-phenyl-tetrahydrofuran ( 2b) and 2-(3′,4′-dimethoxyphenyl)-3-carbamoyl-4-methylenetetrahydrofuran ( 2c), respectively, in very high yields. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.01.071