α-Alkylation of ketones with primary alcohols driven by visible light and bimetallic gold and palladium nanoparticles supported on transition metal oxide

被引:18
作者
Bai, Meifen [1 ]
Xin, Hui [1 ]
Guo, Zhi [1 ]
Guo, Dapeng [1 ]
Wang, Yan [1 ]
Zhao, Peng [1 ]
Li, Jingyi [1 ]
机构
[1] Inner Mongolia Univ, Coll Chem & Chem Engn, Hohhot 010021, Inner Mongolia, Peoples R China
基金
中国国家自然科学基金;
关键词
alpha-Alkylation; Ketones; Primary alcohols; Visible light; Bimetallic photo-catalysts; SURFACE-PLASMON RESONANCE; AEROBIC OXIDATION; CATALYST; PHOTOCATALYST; NANOPALLADIUM; DEGRADATION; IRRADIATION; REDUCTION; STRATEGY; SOLVENT;
D O I
10.1016/j.apsusc.2016.07.020
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The direct a-alkylation of ketones with primary alcohols to obtain the corresponding saturated coupled ketones was achieved with bimetallic gold(Au)-palladium(Pd) nanoparticles(NPs) supported on a transition metal oxide (such as CeO2). This system demonstrated a higher catalytic property than Au/CeO2 and Pd/CeO2 under visible light irradiation at 40 +/- 3 degrees C in an Ar atmosphere. Such phenomenon was caused by the synergistic effect between Au and Pd. Isopropyl alcohol was used as the solvent and CH3ONa as the base. The effect of the bimetallic Au-Pd mass ratio and the two different transition metal oxide supports (such as CeO2 or ZrO2) during the reaction process was studied. The highest catalytic activity of those examined happened with the 1.5 wt% Au-1.5 wt%Pd (Au and Pd mass ratio I :1)/CeO2 photo-catalyst. The intensity and wavelength of the visible light had a strong influence on the system. The catalyst can be reused for four times. A reaction mechanism was proposed for the a-alkylation of ketones with primary alcohols. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码:617 / 626
页数:10
相关论文
共 44 条
  • [1] Efficiency in chemistry: from hydrogen autotransfer to multicomponent catalysis
    Alonso, Francisco
    Foubelo, Francisco
    Gonzalez-Gomez, Jose C.
    Martinez, Ricardo
    Ramon, Diego J.
    Riente, Paola
    Yus, Miguel
    [J]. MOLECULAR DIVERSITY, 2010, 14 (03) : 411 - 424
  • [2] Iridium catalysed chemoselective alkylation of 2′-aminoacetophenone with primary benzyl type alcohols under microwave conditions
    Bhat, Shailen
    Sridharan, Visuvanathar
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (39) : 4701 - 4703
  • [3] Plasmonic Au/CdMoO4 photocatalyst: Influence of surface plasmon resonance for selective photocatalytic oxidation of benzylic alcohol
    Bi, Jinhong
    Zhou, Zhiyong
    Chen, Mengying
    Liang, Shijing
    He, Yunhui
    Zhang, Zizhong
    Wu, Ling
    [J]. APPLIED SURFACE SCIENCE, 2015, 349 : 292 - 298
  • [4] The Vinylogous Aldol and Related Addition Reactions: Ten Years of Progress
    Casiraghi, Giovanni
    Battistini, Lucia
    Curti, Claudio
    Rassu, Gloria
    Zanardi, Franca
    [J]. CHEMICAL REVIEWS, 2011, 111 (05) : 3076 - 3154
  • [5] Supported silver nanoparticles as photocatalysts under ultraviolet and visible light irradiation
    Chen, Xi
    Zheng, Zhanfeng
    Ke, Xuebin
    Jaatinen, Esa
    Xie, Tengfeng
    Wang, Dejun
    Guo, Cheng
    Zhao, Jincai
    Zhu, Huaiyong
    [J]. GREEN CHEMISTRY, 2010, 12 (03) : 414 - 419
  • [6] Ruthenium-catalyzed reductive coupling between ketones and primary alcohols in the presence of ethylenediamine
    Cho, Chan Sik
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 267 (1-2) : 49 - 52
  • [7] Organic Ligand-Free Alkylation of Amines, Carboxamides, Sulfonamides, and Ketones by Using Alcohols Catalyzed by Heterogeneous Ag/Mo Oxides
    Cui, Xinjiang
    Zhang, Yan
    Shi, Feng
    Deng, Youquan
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (03) : 1021 - 1028
  • [8] Dehydrogenation as a Substrate-Activating Strategy in Homogeneous Transition-Metal Catalysis
    Dobereiner, Graham E.
    Crabtree, Robert H.
    [J]. CHEMICAL REVIEWS, 2010, 110 (02) : 681 - 703
  • [9] Ultrafast plasmon induced electron injection mechanism in gold-TiO2 nanoparticle system
    Du, Luchao
    Furube, Akihiro
    Hara, Kohjiro
    Katoh, Ryuzi
    Tachiya, Masanori
    [J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY C-PHOTOCHEMISTRY REVIEWS, 2013, 15 : 21 - 30
  • [10] Iridium-Catalyzed α-Alkylation of Acetates with Primary Alcohols and Diols
    Iuchi, Yosuke
    Obora, Yasushi
    Ishii, Yasutaka
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (08) : 2536 - +