A Masked Cuprous Hydride as a Catalyst for Carbonyl Hydrosilylation in Aqueous Solutions

被引:22
|
作者
Ritter, Florian [1 ]
Mukherjee, Debabrata [1 ,2 ]
Spaniol, Thomas P. [1 ]
Hoffmann, Alexander [1 ]
Okuda, Jun [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Inorgan Chem, Landoltweg 1, D-52056 Aachen, Germany
[2] Indian Inst Technol Kharagpur, Dept Chem, Kharagpur 721302, W Bengal, India
关键词
carbonyl reduction; catalysis in water; copper; hydridotriphenylborate; hydrosilylation; COPPER HYDRIDE; CRYSTALLOGRAPHIC CHARACTERIZATION; CONJUGATE REDUCTION; COMPLEXES; REACTIVITY; NA; TRANSFORMATIONS; REAGENT; LIGAND; WATER;
D O I
10.1002/anie.201811890
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Redox-unstable cuprous hydridotriphenylborate was isolated as an N-heterocyclic carbene adduct [(IPr)Cu-(HBPh3)] (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) with good thermal stability. Although this compound displays a contact ion-pair structure, (CuH)-H-I-like catalytic activity was envisaged in carbonyl hydrosilylation. Sufficient moisture stability allowed the catalysis in aqueous/organic media. Mechanistic study further showed that a phenyl group on the borate anion is abstracted by [(IPr)Cu](+) to give the cationic organocopper complex [(IPr)(2)Cu-2(mu-Ph)][BPh4].
引用
收藏
页码:1818 / 1822
页数:5
相关论文
共 50 条
  • [21] Unusual Structure, Fluxionality, and Reaction Mechanism of Carbonyl Hydrosilylation by Silyl Hydride Complex [(ArN)Mo(H)(SiH2Ph)(PMe3)3]
    Khalimon, Andrey Y.
    Ignatov, Stanislav K.
    Okhapkin, Andrey I.
    Simionescu, Razvan
    Kuzmina, Lyudmila G.
    Howard, Judith A. K.
    Nikonov, Georgii I.
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (26) : 8573 - 8590
  • [22] Carbonyl-Amplified Catalyst Performance: Balancing Stability against Activity for Five-Coordinate Ruthenium Hydride and Hydridocarbonyl Catalysts
    Beach, Nicholas J.
    Blacquiere, Johanna M.
    Drouin, Samantha D.
    Fogg, Deryn E.
    ORGANOMETALLICS, 2009, 28 (02) : 441 - 447
  • [23] Selective C-F and C-H Activation of Fluoroarenes by Fe(PMe3)4 and Catalytic Performance of Iron Hydride in Hydrosilylation of Carbonyl Compounds
    Zheng, Tingting
    Li, Junye
    Zhang, Shumiao
    Xue, Benjing
    Sun, Hongjian
    Li, Xiaoyan
    Fuhr, Olaf
    Fenske, Dieter
    ORGANOMETALLICS, 2016, 35 (20) : 3538 - 3545
  • [24] Catalytic hydrodechlorination reactivity of monochlorophenols in aqueous solutions over palladium/carbon catalyst
    Xia, Chuanhai
    Liu, Ying
    Xu, Jie
    Yu, Junbao
    Qin, Wei
    Liang, Xinmiao
    CATALYSIS COMMUNICATIONS, 2009, 10 (05) : 456 - 458
  • [25] [Rh(OH)(cod)]2 (cod=1,5-cyclooctadiene):: A highly efficient catalyst for 1,4-hydrosilylation of α,β-unsaturated carbonyl compounds
    Mori, A
    Kato, T
    SYNLETT, 2002, (07) : 1167 - 1169
  • [26] Reaction Kinetics of Vanillin Hydrogenation in Aqueous Solutions Using a Ru/C Catalyst
    Bindwal, Ankush B.
    Vaidya, Prakash D.
    ENERGY & FUELS, 2014, 28 (05) : 3357 - 3362
  • [27] Chemiluminescence initiated by nebulization of oxidant- and catalyst-free aqueous luminol solutions
    Jiang, Yang
    Yang, Xia
    Li, Sijia
    Qiao, Yanxia
    Zhou, Yaqian
    Li, Yan
    CHEMICAL ENGINEERING JOURNAL, 2024, 481
  • [28] Recovery of Metal Ions from Aqueous Solutions by γ-Alumina Creates Value-Added Catalyst Products
    Lee, Chung-Seop
    Rho, Hojung
    Sharma, Naushita
    Jung, Bongyeon
    Westerhoff, Paul
    ACS ES&T WATER, 2023, 3 (08): : 2481 - 2490
  • [29] Aqueous Biphasic Systems for the Synthesis of Formates by Catalytic CO2 Hydrogenation: Integrated Reaction and Catalyst Separation for CO2-Scrubbing Solutions
    Scott, Martin
    Molinos, Beatriz Blas
    Westhues, Christian
    Francio, Giancarlo
    Leitner, Walter
    CHEMSUSCHEM, 2017, 10 (06) : 1085 - 1093
  • [30] Ru(III) single site solid micellar catalyst for selective aqueous phase hydrogenation of carbonyl groups in biomass-derived compounds
    Wang, Qiyan
    Santos, Sara
    Urbina-Blanco, Cesar A.
    Zhou, Wenjuan
    Yang, Yong
    Marinova, Maya
    Heyte, Svetlana
    Joelle, Thuriot-Roukos
    Ersen, Ovidiu
    Baaziz, Walid
    Safonova, Olga, V
    Saeys, Mark
    Ordomsky, Vitaly V.
    APPLIED CATALYSIS B-ENVIRONMENTAL, 2022, 300