Continuous Flow Synthesis of [Au(NHC)(Aryl)] (NHC=N-Heterocyclic Carbene) Complexes

被引:9
|
作者
Cauwenbergh, Thibault [1 ,2 ]
Tzouras, Nikolaos, V [1 ,2 ]
Scattolin, Thomas [1 ,2 ]
Bhandary, Subhrajyoti [1 ,2 ]
Simoens, Andreas [3 ]
Van Hecke, Kristof [1 ,2 ]
Stevens, Christian, V [3 ]
Nolan, Steven P. [1 ,2 ]
机构
[1] Univ Ghent, Dept Chem, Krijgslaan 281,S3, B-9000 Ghent, Belgium
[2] Univ Ghent, Ctr Sustainable Chem, Krijgslaan 281,S3, B-9000 Ghent, Belgium
[3] Univ Ghent, Dept Green Chem & Technol Synth, Biosources & Bioorgan Chem SynBioC Res Grp, Coupure Links 653, B-9000 Ghent, Belgium
基金
比利时弗兰德研究基金会;
关键词
continuous-flow synthesis; gold(I)-aryl; N-heterocyclic carbenes; sustainability; weak-base routes; TRANSMETALATION; REACTIVITY; GOLD(I); ROUTES;
D O I
10.1002/chem.202102379
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The use of weak and inexpensive bases has recently opened promising perspectives towards the simpler and more sustainable synthesis of Au(I)-aryl complexes with valuable applications in catalysis, medicinal chemistry, and materials science. In recent years, continuous manufacturing has shown to be a reliable partner in establishing sustainable and controlled process scalability. Herein, the first continuous flow synthesis of a range of Au(I)-aryl starting from widely available boronic acids and various [Au(NHC)Cl] (NHC=N-heterocyclic carbene) complexes in unprecedentedly short reaction times and high yields is reported. Successful synthesis of previously non- or poorly accessible complexes exposed fascinating reactivity patterns. Via a gram-scale synthesis, convenient process scalability of the developed protocol was showcased.
引用
收藏
页码:13342 / 13345
页数:4
相关论文
共 50 条
  • [41] Mechanochemical Synthesis of Corannulene Flanked N-heterocyclic Carbene (NHC) Precursors and Preparation of Their Metal Complexes
    Hum, Gavin
    Muzammil, Ezzah M.
    Li, Yongxin
    Garcia, Felipe
    Stuparu, Mihaiela C.
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (50)
  • [42] A general synthetic route to mixed NHC-phosphane palladium(0) complexes (NHC = N-heterocyclic carbene)
    Fantasia, Serena
    Nolan, Steven P.
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (23) : 6987 - 6993
  • [43] N-Heterocyclic Carbene (NHC) Binuclear Gold Complexes Catalyzed Aminoarylation of Olefins
    Zhang Rui
    Xu Qin
    Shi Min
    ACTA CHIMICA SINICA, 2012, 70 (15) : 1593 - 1598
  • [44] Two chromium(II) acetate complexes with N-heterocyclic carbene (NHC) coligands
    Heiser, Christian
    Merzweiler, Kurt
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2024, 80 : 811 - +
  • [45] Synthesis and reactivity of N-heterocyclic carbene (NHC)-supported heavier nitrile ylides
    Sarkar, Debotra
    Dutta, Sayan
    Hanusch, Franziska
    Koley, Debasis
    Inoue, Shigeyoshi
    CHEMICAL SCIENCE, 2024, 15 (07) : 2391 - 2397
  • [46] Activation and reactivity of (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes in cross-coupling reactions
    Viciu, MS
    Germaneau, RF
    Navarro-Fernandez, O
    Stevens, ED
    Nolan, SP
    ORGANOMETALLICS, 2002, 21 (25) : 5470 - 5472
  • [47] Electronic properties of n-heterocyclic carbene (NHC) ligands: Synthetic, structural, and spectroscopic studies of (NHC)Platinum(II) complexes
    Fantasia, Serena
    Petersen, Jeffrey L.
    Jacobsen, Heiko
    Cavallo, Luigi
    Nolan, Steven P.
    ORGANOMETALLICS, 2007, 26 (24) : 5880 - 5889
  • [48] Imidazoliophosphines are True N-Heterocyclic Carbene (NHC)-Phosphenium Adducts
    Abdellah, Ibrahim
    Lepetit, Christine
    Canac, Yves
    Duhayon, Carine
    Chauvin, Remi
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (44) : 13095 - 13108
  • [49] Synthesis and structural characterization of N-heterocyclic carbene(NHC) vanadium(V) oxo-halide complexes
    Wargolet, Megan M.
    Spicer, Mark D.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [50] Palladium catalyzed amination of aryl triflates using (NHC)Pd(allyl)Cl (NHC=N-heterocyclic carbene) catalysts.
    Kaur, H
    Viciu, MS
    Fernandez, ON
    Nolan, SP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U130 - U130