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

被引：20
作者：
Esteves, A. P. [1 ]
Ferreira, E. C. [1 ]
Medeiros, M. J. [1 ]
机构：
[1] Univ Minho, Ctr Quim, P-4705553 Braga, Portugal
来源：
TETRAHEDRON | 2007年 / 63卷 / 14期
关键词：
electrosynthesis; electrocatalytic reduction; intramolecular cyclisation; Nickel(I) tetramethylcyclam;
D O I：
10.1016/j.tet.2007.01.071
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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/Et4NBF4 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. (c) 2007 Elsevier Ltd. All rights reserved.
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页码：3006 / 3009
页数：4
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