Organic Ligand-Free Alkylation of Amines, Carboxamides, Sulfonamides, and Ketones by Using Alcohols Catalyzed by Heterogeneous Ag/Mo Oxides

被引:176
作者
Cui, Xinjiang [1 ,2 ]
Zhang, Yan [1 ]
Shi, Feng [1 ]
Deng, Youquan [1 ]
机构
[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, Ctr Green Chem & Catalysis, Lanzhou 730000, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
关键词
Ag/Mo; amines; carboxamides; ketones; sulfonamides; N-ALKYLATION; ARYL HALIDES; BORROWING HYDROGEN; DIRECT AMINATION; AMIDE SYNTHESIS; INTRAMOLECULAR HYDROAMINATION; RUTHENIUM COMPLEXES; DIRECT SUBSTITUTION; ALLYLIC ALCOHOLS; AROMATIC-AMINES;
D O I
10.1002/chem.201001915
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Complicated and expensive organic ligands are normally essential in fine chemical synthesis at preparative or industrial levels. The synthesis of fine chemicals by using heterogeneous catalyst systems without additive organic ligand is highly desirable but severely limited due to their poor generality and rigorous reaction conditions. Here, we show the results of carbon nitrogen or carbon carbon bond formation catalyzed by an Ag/Mo hybrid material with specific Ag6Mo10O33 crystal structure. 48 nitrogen- or oxygen-containing compounds, that is, amines, carboxamides, sulfonamides, and ketones, were successfully synthesized through a borrowing-hydrogen mechanism. Up to 99% isolated yields were obtained under relatively mild conditions without additive organic ligand. The catalytic process shows promise for the efficient and economic synthesis of amine, carboxamide, sulfonamide, and ketone derivatives because of the simplicity of the system and ease of operation.
引用
收藏
页码:1021 / 1028
页数:8
相关论文
共 69 条
  • [1] Amines made easily: A highly selective hydroaminomethylation of olefins
    Ahmed, M
    Seayad, AM
    Jackstell, R
    Beller, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) : 10311 - 10318
  • [2] AHMED M, 2007, J AM CHEM SOC, V13, P1594
  • [3] [Anonymous], 2010, Angew. Chem., DOI DOI 10.1002/ANGE.200905684
  • [4] Ion Exchange Resins: Catalyst Recovery and Recycle
    Barbaro, Pierluigi
    Liguori, Francesca
    [J]. CHEMICAL REVIEWS, 2009, 109 (02) : 515 - 529
  • [5] An efficient method for the selective iridium-catalyzed monoalkylation of (hetero)aromatic amines with primary alcohols
    Blank, Benoit
    Madalska, Martyna
    Kempe, Rhett
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (05) : 749 - 758
  • [6] Selective Iridium-Catalyzed Alkylation of (Hetero) Aromatic Amines and Diamines with Alcohols under Mild Reaction Conditions
    Blank, Benoit
    Michlik, Stefan
    Kempe, Rhett
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (15) : 3790 - 3799
  • [7] Industrial-scale palladium-catalyzed coupling of aryl halides and amines - A personal account
    Buchwald, SL
    Mauger, C
    Mignani, G
    Scholz, U
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) : 23 - 39
  • [8] Sustainable Preparation of Supported Metal Nanoparticles and Their Applications in Catalysis
    Campelo, Juan M.
    Luna, Diego
    Luque, Rafael
    Marinas, Jose M.
    Romero, Antonio A.
    [J]. CHEMSUSCHEM, 2009, 2 (01) : 18 - 45
  • [9] CuCl catalyst heterogenized on diamide immobilized SBA-15 for efficient oxidative carbonylation of methanol to dimethylcarbonate
    Cao, Y
    Hu, JC
    Yang, P
    Dai, WL
    Fan, KN
    [J]. CHEMICAL COMMUNICATIONS, 2003, (07) : 908 - 909
  • [10] Copper-Catalyzed N-Alkylation of Sulfonamides with Benzylic Alcohols: Catalysis and Mechanistic Studies
    Cui, Xinjiang
    Shi, Feng
    Tse, Man Kin
    Goerdes, Dirk
    Thurow, Kerstin
    Beller, Matthias
    Deng, Youquan
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (17) : 2949 - 2958