Alcohols for the α-Alkylation of Methyl Ketones and Indirect Aza-Wittig Reaction Promoted by Nickel Nanoparticles

被引：108
作者：
Alonso, Francisco [1 ,2 ]
Riente, Paola [1 ,2 ]
Yus, Miguel [1 ,2 ]
机构：
[1] Univ Alicante, Dept Quim Organ, Fac Ciencias, E-03080 Alicante, Spain
[2] Univ Alicante, ISO, E-03080 Alicante, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 29期
关键词：
Alcohols; Ketone alkylation; Hydrogen transfer; Nickel nanoparticles; Aza-Wittig reactions;
D O I：
10.1002/ejoc.200800729
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Nickel nanoparticles have been found to activate primary alcohols used for the alpha-alkylation of ketones or in indirect aza-Wittig reactions. These processes involve hydrogen transfer from the alcohol to the intermediate alpha,beta-unsaturated ketone or imine, respectively. All these reactions are carried out in the absence of any ligand, hydrogen acceptor or base under mild reaction conditions. For the first time nickel is employed as a potential alternative to noble-metal-based catalysts in both reactions. A reaction mechanism is proposed on the basis of some deuteration experiments. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
引用
收藏
页码：4908 / 4914
页数：7
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共 47 条
  • [1] Preparation of nickel(0) nanoparticles by arene-catalysed reduction of different nickel chloride-containing systems
    Alonso, F.
    Calvino, J. J.
    Osante, I.
    Yus, M.
    [J]. JOURNAL OF EXPERIMENTAL NANOSCIENCE, 2006, 1 (04) : 419 - 433
  • [2] The NiCl2-Li-arene(cat.) combination: A versatile reducing mixture
    Alonso, F
    Yus, M
    [J]. CHEMICAL SOCIETY REVIEWS, 2004, 33 (05) : 284 - 293
  • [3] Homocoupling of aryl iodides promoted by nickel(0) nanoparticles
    Alonso, Francisco
    Riente, Paola
    Yus, Miguel
    [J]. ARKIVOC, 2008, : 8 - 15
  • [4] Hydrogen-transfer reductive amination of aldehydes catalysed by nickel nanoparticles
    Alonso, Francisco
    Riente, Paola
    Yus, Miguel
    [J]. SYNLETT, 2008, (09) : 1289 - 1292
  • [5] Hydrogen-transfer reduction of carbonyl compounds promoted by nickel nanoparticles
    Alonso, Francisco
    Riente, Paola
    Yus, Miguel
    [J]. TETRAHEDRON, 2008, 64 (08) : 1847 - 1852
  • [6] Hydrogen-transfer reduction of carbonyl compounds catalysed by nickel nanoparticles
    Alonso, Francisco
    Riente, Paola
    Yus, Miguel
    [J]. TETRAHEDRON LETTERS, 2008, 49 (12) : 1939 - 1942
  • [7] New synthetic methodologies based on active transition metals
    Alonso, Francisco
    Yust, Miguel
    [J]. PURE AND APPLIED CHEMISTRY, 2008, 80 (05) : 1005 - 1012
  • [8] The α-alkylation of methyl ketones with primary alcohols promoted by nickel nanoparticles under mild and ligandless conditions
    Alonso, Francisco
    Riente, Paola
    Yus, Miguel
    [J]. SYNLETT, 2007, (12) : 1877 - 1880
  • [9] Highly selective hydrogenation of multiple carbon-carbon bonds promoted by nickel(0) nanoparticles
    Alonso, Francisco
    Osante, Inaki
    Yus, Miguel
    [J]. TETRAHEDRON, 2007, 63 (01) : 93 - 102
  • [10] Conjugate reduction of α,β-unsaturated carbonyl compounds promoted by nickel nanoparticles
    Alonso, Francisco
    Osante, Inaki
    Yus, Miguel
    [J]. SYNLETT, 2006, (18) : 3017 - 3020
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