Hydrogen-transfer reduction of carbonyl compounds promoted by nickel nanoparticles

被引：103

作者：

Alonso, Francisco ^{[1
,2
]}

Riente, Paola ^{[1
,2
]}

Yus, Miguel ^{[1
,2
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain

[2] Univ Alicante, Inst Sintesis Organ, E-03080 Alicante, Spain

来源：

TETRAHEDRON | 2008年 / 64卷 / 08期

关键词：

carbonyl compounds; nickel nanoparticles; hydrogen transfer;

D O I：

10.1016/j.tet.2007.11.093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nickel(0) nanoparticles, generated from nickel(II) chloride, lithium powder and a catalytic amount of 4,4-di-tert-butylbiphenyl (DTBB) in THF at room temperature, have been found to promote the reduction of a variety of ketones and aldehydes by transfer hydrogenation using isopropanol as the hydrogen donor. The nickel nanoparticles were characterised and could be re-utilised with a good performance in the absence of a base. A mechanistic study demonstrates that the reaction proceeds through a dihydride-type mechanism. (C) 2007 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1847 / 1852

页数：6

相关论文

共 45 条

[1] 1H chemical shifts in NMR:: Part 23, the effect of dimethyl sulphoxide versus chloroform solvent on 1H chemical shifts [J].

Abraham, RJ ;

Byrne, JJ ;

Griffiths, L ;

Perez, M .

MAGNETIC RESONANCE IN CHEMISTRY, 2006, 44 (05) :491-509

[2] Preparation of nickel(0) nanoparticles by arene-catalysed reduction of different nickel chloride-containing systems [J].

Alonso, F. ;

Calvino, J. J. ;

Osante, I. ;

Yus, M. .

JOURNAL OF EXPERIMENTAL NANOSCIENCE, 2006, 1 (04) :419-433

[3] Highly stereoselective semihydrogenation of alkynes promoted by nickel(0) nanoparticles [J].

Alonso, F ;

Osante, M ;

Yus, M .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (03) :305-308

[4] A new straightforward and mild preparation of nickel(0) nanoparticles [J].

Alonso, F ;

Calvino, JJ ;

Osante, I ;

Yus, M .

CHEMISTRY LETTERS, 2005, 34 (09) :1262-1263

[5] The NiCl2-Li-arene(cat.) combination: A versatile reducing mixture [J].

Alonso, F ;

Yus, M .

CHEMICAL SOCIETY REVIEWS, 2004, 33 (05) :284-293

[6] The NiCl2•2H2O-Li-arene combination as reducing system.: Part 3.: Reduction of carbonyl compounds and imines [J].

Alonso, F ;

Yus, M .

TETRAHEDRON, 1998, 54 (09) :1921-1928

[7] The α-alkylation of methyl ketones with primary alcohols promoted by nickel nanoparticles under mild and ligandless conditions [J].

Alonso, Francisco ;

Riente, Paola ;

Yus, Miguel .

SYNLETT, 2007, (12) :1877-1880

[8] Highly selective hydrogenation of multiple carbon-carbon bonds promoted by nickel(0) nanoparticles [J].

Alonso, Francisco ;

Osante, Inaki ;

Yus, Miguel .

TETRAHEDRON, 2007, 63 (01) :93-102

[9] Conjugate reduction of α,β-unsaturated carbonyl compounds promoted by nickel nanoparticles [J].

Alonso, Francisco ;

Osante, Inaki ;

Yus, Miguel .

SYNLETT, 2006, (18) :3017-3020

[10]

ANDREWS MJ, 1978, INDIAN J CHEM B, V16, P465

← 1 2 3 4 5 →