Electrochemical reduction of allyl ethers in the presence of nickel complexes: A review of synthetic applications

被引:11
作者
Olivero, S
Franco, D
Clinet, JC
Dunach, E [1 ]
机构
[1] Univ Nice, CNRS, Chim Bioorgan Lab, F-06108 Nice 2, France
[2] Univ Paris 11, CNRS, Inst Chim Mol, F-95405 Orsay, France
关键词
electrochemical reductions; nickel; allyl ethers; cleavage; cyclization; protecting groups; bipyridine ligands;
D O I
10.1135/cccc20000844
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This review deals with the electrochemical reactivity of a family of organic compounds, namely allyl ether derivatives, in the presence of various catalytic systems. Essentially, nickel complexes associated with various ligands have been described for such reactions. The electrochemical reduction of allyl aryl ethers has been reported to be very dependent on the nature of the catalytic system. Ni(II) complexes with 2,2'-bipyridine ligands selectively catalyze the cleavage of the O-C(allyl) bond to afford the corresponding alcohol or phenol derivatives in good yields. The related ortho-halogenated allyl ether substrates, in the presence of Ni(II) catalysts with cyclam-type macrocyclic ligands undergo intramolecular cyclizations. The nature of the ligand on nickel strongly influences the reactivity and the chemoselectivity of these processes. A review with 62 references.
引用
收藏
页码:844 / 861
页数:18
相关论文
共 77 条
[1]   ACTIVATION OF CARBON-DIOXIDE BY ELECTRON-TRANSFER AND TRANSITION-METALS - MECHANISM OF NICKEL-CATALYZED ELECTROCARBOXYLATION OF AROMATIC HALIDES [J].
AMATORE, C ;
JUTAND, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (08) :2819-2825
[2]   MECHANISM OF NICKEL-CATALYZED ELECTRON-TRANSFER ACTIVATION OF AROMATIC HALIDES .1. BIPHENYL ELECTROSYNTHESIS FROM BROMOBENZENE [J].
AMATORE, C ;
JUTAND, A ;
MOTTIER, L .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1991, 306 (1-2) :125-140
[3]   MECHANISM OF NICKEL-CATALYZED ELECTRON-TRANSFER ACTIVATION OF AROMATIC HALIDES .2. ELECTROCARBOXYLATION OF BROMOBENZENE [J].
AMATORE, C ;
JUTAND, A .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1991, 306 (1-2) :141-156
[4]   FORMATION OF DIHYDROBENZOFURANS BY RADICAL CYCLIZATION [J].
BECKWITH, ALJ ;
MEIJS, GF .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (03) :136-137
[5]   ELECTROCATALYTIC REDUCTION OF CO2 BY NI CYCLAM2+ IN WATER - STUDY OF THE FACTORS AFFECTING THE EFFICIENCY AND THE SELECTIVITY OF THE PROCESS [J].
BELEY, M ;
COLLIN, JP ;
RUPPERT, R ;
SAUVAGE, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (24) :7461-7467
[6]   REDUCTIVE DEPROTECTION OF ARYL ALLYL ETHERS WITH PD(PH3)(4)/NABH4 [J].
BEUGELMANS, R ;
BOURDET, S ;
BIGOT, A ;
ZHU, JP .
TETRAHEDRON LETTERS, 1994, 35 (25) :4349-4350
[7]  
CHAUSSARD J, 1990, SYNTHESIS-STUTTGART, P369
[8]  
CLINET JC, 1995, J ORGANOMET CHEM, V48, P503
[9]   METAL EXCHANGE BETWEEN AN ELECTROGENERATED ORGANONICKEL SPECIES AND ZINC HALIDE - APPLICATION TO AN ELECTROCHEMICAL, NICKEL-CATALYZED REFORMATSKY REACTION [J].
CONAN, A ;
SIBILLE, S ;
PERICHON, J .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) :2018-2024
[10]   SELECTIVE CLEAVAGE OF ALLYL ETHERS UNDER MILD CONDITIONS BY TRANSITION-METAL REAGENTS [J].
COREY, EJ ;
SUGGS, JW .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (18) :3224-3224