Homogeneous electromediated reduction of the 2-cyclohexen-1-one by transition metals

被引：11

作者：

da Silva, AP ^{[1
]}

Maia, ACS ^{[1
]}

Navarro, M ^{[1
]}

机构：

[1] Univ Fed Pernambuco, Dept Quim Fundamental, CCEN, BR-50670901 Recife, PE, Brazil

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 18期

关键词：

electrochemical system; mediated reduction; olefins; ketones;

D O I：

10.1016/j.tetlet.2005.03.047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reduction of the 2-cyclohexen-1-one, mediated by some transition metal ions (Zn2+, Cu2+, Ni2+, Co2+ and Fe2+) and complexes ([Ni-II(bipy)]Br, and [Fe-II(bipy)]Br-2, where bipy = 2,2'-bipyridine), was carried out by using a homogeneous electromediated system: sacrificial anode, nickel cathode, (0.2 M) NaI as supporting electrolyte and undivided cell. A constant current of < 100 mA was applied with a maximum cell potential of 2.0 V. Cyclohexanone was the principal product in major cases yielding 98%. Cyclohexanol was also detected in some cases. The selectivity of the process can be controlled by choosing Ni as mediator and Zn or Ni as sacrificial anode. A more reactive system can be reached when Fe sacrificial anode is used, giving cyclohexanol as major product (87%). (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3233 / 3235

页数：3

共 17 条

[1] ROLE AND EFFECTS OF HALIDE-IONS ON THE RATES AND MECHANISMS OF OXIDATIVE ADDITION OF IODOBENZENE TO LOW-LIGATED ZEROVALENT PALLADIUM COMPLEXES PD0(PPH3)2 [J].

AMATORE, C ;

AZZABI, M ;

JUTAND, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8375-8384

[2] RATES AND MECHANISM OF BIPHENYL SYNTHESIS CATALYZED BY ELECTROGENERATED COORDINATIVELY UNSATURATED NICKEL-COMPLEXES [J].

AMATORE, C ;

JUTAND, A .

ORGANOMETALLICS, 1988, 7 (10) :2203-2214

[3] 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

[4] Preparation of β-hydroxyesters from isoxazolines.: A selective Ni0bpy-catalyzed electrochemical method [J].

Caetano, VF ;

Demnitz, FWJ ;

Diniz, FB ;

Mariz, RM ;

Navarro, M .

TETRAHEDRON LETTERS, 2003, 44 (45) :8217-8220

[5] Two convenient and high-yielding preparations of 6,6′-dimethyl-2,2′-bipyridine by homocoupling of 6-bromopicoline [J].

Cassol, TM ;

Demnitz, FWJ ;

Navarro, M ;

Neves, EAD .

TETRAHEDRON LETTERS, 2000, 41 (43) :8203-8206

[6] Electrochemical homocoupling of 2-bromomethylpyridines catalyzed by nickel complexes [J].

de França, KWR ;

Navarro, M ;

Leonel, É ;

Durandetti, M ;

Nédélec, JY .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (06) :1838-1842

[7] Iron-mediated electrochemical reaction of α-chloroesters with carbonyl compounds [J].

Durandetti, M ;

Meignein, C ;

Périchon, J .

ORGANIC LETTERS, 2003, 5 (03) :317-320

[8] Iron-catalyzed electrochemical allylation of carbonyl compounds by allylic acetates [J].

Durandetti, M ;

Meignein, C ;

Périchon, J .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (08) :3121-3124

[9]

Durandetti M, 1996, NEW J CHEM, V20, P659

[10] Reduction of α,β unsaturated carbonyl compounds by Ni2+-BH4- [J].

Handique, JG ;

Purkayashtha, A ;

Baruah, JB .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 620 (1-2) :90-93

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