Cyclotrimetaphosphate-assisted ruthenium catalyst for the hydration of nitriles and oxidation of primary amines to amides under aerobic conditions in water

被引:4
作者
Chouhan, Kishor Kumar [1 ]
Chowdhury, Deep [1 ]
Mukherjee, Arup [1 ]
机构
[1] Indian Inst Technol Bhilai, Dept Chem, GEC Campus, Raipur 492015, Chhattisgarh, India
关键词
SALTS SYNTHESIS; ALCOHOLS; COMPLEXES; EFFICIENT; ACID; BOND; OXYGENATION; CHEMISTRY; LIGANDS; GOLD;
D O I
10.1039/d3ob00062a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Amide bonds are ubiquitous and regarded as an essential constituent of many biologically active drug molecules and fine chemicals. We report a practical and operationally simple ruthenium-based catalytic system for the hydration of nitriles and aerobic oxidation of primary amines to the corresponding amides. Both reactions proceed without any external oxidant in water under aerobic conditions and exhibit a broad substrate scope. The mechanistic investigation was executed with the aid of control experiments and kinetic and spectroscopic studies of the reaction mixture.
引用
收藏
页码:2429 / 2439
页数:11
相关论文
共 101 条
  • [1] Frontiers in catalytic nitrile hydration: Nitrile and cyanohydrin hydration catalyzed by homogeneous organometallic complexes
    Ahmed, Takiya J.
    Knapp, Spring Melody M.
    Tyler, David R.
    [J]. COORDINATION CHEMISTRY REVIEWS, 2011, 255 (7-8) : 949 - 974
  • [2] Metal-catalysed approaches to amide bond formation
    Allen, C. Liana
    Williams, Jonathan M. J.
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) : 3405 - 3415
  • [3] Asymmetric direct amide synthesis by kinetic amine resolution:: A chiral bifunctional aminoboronic acid catalyzed reaction between a racemic amine and an achiral carboxylic acid
    Arnold, Kenny
    Davies, Bryan
    Herault, Damien
    Whiting, Andrew
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (14) : 2673 - 2676
  • [4] POLYOXOANION-SUPPORTED, ATOMICALLY DISPERSED CYCLOOCTADIENERUTHENIUM(II) COMPLEXES
    ATTANASIO, D
    BACHECHI, F
    SUBER, L
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1993, (15): : 2373 - 2378
  • [5] An efficient catalytic method for the Beckmann rearrangement of ketoximes to amides and aldoximes to nitrites mediated by propylphosphonic anhydride (T3P®)
    Augustine, John Kallikat
    Kumar, Rajesha
    Bombrun, Agnes
    Mandal, Ashis Baran
    [J]. TETRAHEDRON LETTERS, 2011, 52 (10) : 1074 - 1077
  • [6] Beckmann E., 1886, BER DTSCH CHEM GES, V89, P988
  • [7] Nickel-Catalyzed Amide Bond Formation from Methyl Esters
    Ben Halima, Taoufik
    Masson-Makdissi, Jeanne
    Newman, Stephen G.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (39) : 12925 - 12929
  • [8] A Cross-Coupling Approach to Amide Bond Formation from Esters
    Ben Halima, Taoufik
    Vandavasi, Jaya Kishore
    Shkoor, Mohanad
    Newman, Stephen G.
    [J]. ACS CATALYSIS, 2017, 7 (03): : 2176 - 2180
  • [9] THE TRIMETAPHOSPHATE LIGAND IN ORGANOMETALLIC CHEMISTRY - ISOLATION OF TRICARBONYLMANGANESE(I), TRICARBONYLRHENIUM(I), (PENTAMETHYLCYCLOPENTADIENYL)RHODIUM(III), AND (NORBORNADIENE)RHODIUM(I) ADDUCTS
    BESECKER, CJ
    DAY, VW
    KLEMPERER, WG
    [J]. ORGANOMETALLICS, 1985, 4 (03) : 564 - 570
  • [10] TCFH-NMI: Direct Access to N-Acyl Imidazoliums for Challenging Amide Bond Formations
    Beutner, Gregory L.
    Young, Ian S.
    Davies, Merrill L.
    Hickey, Matthew R.
    Park, Hyunsoo
    Stevens, Jason M.
    Ye, Qingmei
    [J]. ORGANIC LETTERS, 2018, 20 (14) : 4218 - 4222