Electroreductive cyclisation of unsaturated halides catalysed by nickel macrocyclic complexes

被引：38

作者：

Duñach, E

Esteves, AP

Freitas, AM

Medeiros, MJ

Olivero, S

机构：

[1] Univ Nice St Antipolis, CNRS, Lab Chim Mol, F-06108 Nice 2, France

[2] Univ Minho, Dept Quim, P-4700320 Braga, Portugal

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 49期

关键词：

electrochemical reactions; cyclisation; nickel; nickel compounds; radicals; radical reaction;

D O I：

10.1016/S0040-4039(99)01845-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The indirect electroreduction of unsaturated aliphatic halides using Ni(II) complexes as electron-transfer mediators is achieved in N,N'-dimethylformamide by constant current electrolysis between a cathode and a sacrificial anode in a diaphragmless cell, Cyclic compounds are obtained in low to high yields in conditions that avoid the usual preparation using organotin reagents. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：8693 / 8696

页数：4

相关论文

共 12 条

[1] THE ELECTROCHEMISTRY OF SQUARE-PLANAR MACROCYCLIC NICKEL-COMPLEXES AND THE REACTION OF NI(I) WITH ALKYL BROMIDES - NICKEL TETRAAMINE COMPLEXES [J].

BECKER, JY ;

KERR, JB ;

PLETCHER, D ;

ROSAS, R .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1981, 117 (01) :87-99

[2]

CHAUSSARD J, 1990, SYNTHESIS-STUTTGART, P369

[3]

Giese B., 2004, Organic Reactions, P301, DOI [10.1002/0471264180.or048.02, DOI 10.1002/0471264180.OR048.02]

[4]

HEVELSTON M, 1992, J AM CHEM SOC, V114, P8490

[5] THIAZOLES IN ORGANIC-SYNTHESIS - NOVEL SYNTHESES OF MENTHANES AND EREMOPHILANES [J].

JACOBI, PA ;

EGBERTSON, M ;

FRECHETTE, RF ;

MIAO, CK ;

WEISS, KT .

TETRAHEDRON, 1988, 44 (11) :3327-3338

[6] INSITU ELECTROGENERATION OF [2,2'-ETHYLENEBIS(NITRILOMETHYLIDYNE)DIPHENOLATO]NICKELATE(I) - NICKEL(I) SALEN - AS A CATALYST FOR REDUCTIVE INTRAMOLECULAR CYCLIZATIONS OF 6-IODO-1-PHENYL-1-HEXYNE AND 6-BROMO-1-PHENYL-1-HEXYNE [J].

MUBARAK, MS ;

PETERS, DG .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1992, 332 (1-2) :127-134

[7] Electrochemical studies of Ni(cyclam)2+-catalyzed annulation reactions [J].

Olivero, S ;

Rolland, JP ;

Dunach, E .

ORGANOMETALLICS, 1998, 17 (17) :3747-3753

[8] ELECTROCHEMICAL INTRAMOLECULAR REDUCTIVE CYCLIZATION CATALYZED BY ELECTROGENERATED NI(CYCLAM)(2+) [J].

OLIVERO, S ;

CLINET, JC ;

DUNACH, E .

TETRAHEDRON LETTERS, 1995, 36 (25) :4429-4432

[9]

OLIVERO S, 1994, SYNLETT, P531

[10] INDIRECT ELECTROREDUCTIVE CYCLIZATION OF N-ALLYLIC AND N-PROPARGYLBROMO AMIDES AND O-BROMOACRYLOYLANILIDES USING NICKEL(II) COMPLEXES AS ELECTRON-TRANSFER CATALYSTS [J].

OZAKI, S ;

MATSUSHITA, H ;

OHMORI, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (19) :2339-2344