Use of a Cyclometalated Iridium(III) Complex Containing a N∧C∧N-Coordinating Terdentate Ligand as a Catalyst for the α-Alkylation of Ketones and N-Alkylation of Amines with Alcohols

被引:67
作者
Liu, Pengcheng [1 ]
Lang, Ran [1 ]
Lu, Lei [1 ]
Yu, Zhentao [2 ]
Li, Feng [1 ]
机构
[1] Nanjing Univ Sci & Technol, Sch Chem Engn, Nanjing 210094, Jiangsu, Peoples R China
[2] Nanjing Univ, Coll Engn & Appl Sci, Jiangsu Key Lab Nano Technol, Nanjing 210093, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
TRANSITION-METAL; CHEMOSELECTIVE HYDROGENATION; SELECTIVE ALKYLATION; RECYCLABLE CATALYST; REDUCTIVE AMINATION; EFFICIENT CATALYSTS; BORROWING HYDROGEN; PALLADIUM CATALYST; HIGHLY EFFICIENT; WATER OXIDATION;
D O I
10.1021/acs.joc.6b02758
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A cyclometalated iridium(III) complex containing a N boolean AND C boolean AND N-coordinating terdentate ligand [Ir(dpyx-N,C,N)-Cl(mu-Cl)](2) was found to be a general and highly effective catalyst for the a-alkylation of ketones and N-alkylation of amines with alcohols. In the presence of catalyst (1 mol % Ir) and base (0.2-0.5 equiv), a variety of desirable products were obtained in good yields under an air atmosphere. Notably, this research exhibited the new potential of Ir(III) complexes bearing non-Cp* ligand and will facilitate the progress of the hydrogen autotransfer process.
引用
收藏
页码:1943 / 1950
页数:8
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  • [1] Selective Alkylation of (Hetero)Aromatic Amines with Alcohols Catalyzed by a Ruthenium Pincer Complex
    Agrawal, Santosh
    Lenormand, Maud
    Martin-Matute, Belen
    [J]. ORGANIC LETTERS, 2012, 14 (06) : 1456 - 1459
  • [2] The Catalytic Amination of Alcohols
    Baehn, Sebastian
    Imm, Sebastian
    Neubert, Lorenz
    Zhang, Min
    Neumann, Helfried
    Beller, Matthias
    [J]. CHEMCATCHEM, 2011, 3 (12) : 1853 - 1864
  • [3] Molecular Catalysts for Water Oxidation
    Blakemore, James D.
    Crabtree, Robert H.
    Brudvig, Gary W.
    [J]. CHEMICAL REVIEWS, 2015, 115 (23) : 12974 - 13005
  • [4] Catalytic Alkylation of Methyl-N-Heteroaromatics with Alcohols
    Blank, Benoit
    Kempe, Rhett
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (03) : 924 - +
  • [5] Luminescent Iridium(III) Complexes with N∧C∧N-Coordinated Terdentate Ligands: Dual Tuning of the Emission Energy and Application to Organic Light-Emitting Devices
    Brulatti, Pierpaolo
    Gildea, Richard J.
    Howard, Judith A. K.
    Fattori, Valeria
    Cocchi, Massimo
    Williams, J. A. Gareth
    [J]. INORGANIC CHEMISTRY, 2012, 51 (06) : 3813 - 3826
  • [6] Osmium Catalyst for the Borrowing Hydrogen Methodology: α-Alkylation of Arylacetonitriles and Methyl Ketones
    Buil, Maria L.
    Esteruelas, Miguel A.
    Herrero, Juana
    Izquierdo, Susana
    Pastor, Isidro M.
    Yus, Miguel
    [J]. ACS CATALYSIS, 2013, 3 (09): : 2072 - 2075
  • [7] Dinuclear Iridium(III) Complexes Containing Bibenzimidazole and Their Application to Water Photoreduction
    Cai, Jian-Guang
    Yu, Zhen-Tao
    Yuan, Yong-Jun
    Li, Feng
    Zou, Zhi-Gang
    [J]. ACS CATALYSIS, 2014, 4 (06): : 1953 - 1963
  • [8] First Cp*-functionalized N-heterocyclic carbene and its coordination to iridium. study of the catalytic properties
    da Costa, Andre Pontes
    Viciano, Monica
    Sanau, Mercedes
    Merino, Sonia
    Tejeda, Juan
    Peris, Eduardo
    Royo, Beatriz
    [J]. ORGANOMETALLICS, 2008, 27 (06) : 1305 - 1309
  • [9] A conjugated ketone as a catalyst in alcohol amination reactions under transition-metal and hetero-atom free conditions
    Dai, Xingchao
    Cui, Xinjiang
    Deng, Youquan
    Shi, Feng
    [J]. RSC ADVANCES, 2015, 5 (54): : 43589 - 43593
  • [10] Iridium Dihydroxybipyridine Complexes Show That Ligand Deprotonation Dramatically Speeds Rates of Catalytic Water Oxidation
    DePasquale, Joseph
    Nieto, Ismael
    Reuther, Lauren E.
    Herbst-Gervasoni, Corey J.
    Paul, Jared J.
    Mochalin, Vadym
    Zeller, Matthias
    Thomas, Christine M.
    Addison, Anthony W.
    Papish, Elizabeth T.
    [J]. INORGANIC CHEMISTRY, 2013, 52 (16) : 9175 - 9183