Developing a Highly Active Catalytic System Based on Cobalt Nanoparticles for Terminal and Internal Alkene Hydrosilylation

被引:25
|
作者
Jakoobi, Martin [1 ]
Dardun, Vincent [1 ]
Veyre, Laurent [1 ]
Meille, Valerie [2 ]
Camp, Clement [1 ]
Thieuleux, Chloe [1 ]
机构
[1] Univ Lyon, Inst Chim Lyon, Lab Chem Catalysis Polymers & Proc, C2P2,UMR 5265,CNRS,UCB Lyon 1,CPE Lyon, F-69616 Villeurbanne, France
[2] Univ Lyon, Inst Chim Lyon, Lab Genie Proc Catalyt, UMR 5285,CNRS,UCB Lyon 1,CPE Lyon, F-69616 Villeurbanne, France
来源
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 18期
关键词
MAGNETIC-PROPERTIES; IRON CATALYSTS; ALLYL ESTERS; COMPLEXES; LIGANDS; SELECTIVITY; ACTIVATION; PRECURSOR; EFFICIENT; SILANES;
D O I
10.1021/acs.joc.0c01439
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This work describes the development of easy-to-prepare cobalt nanoparticles (NPs) in solution as promising alternative catalysts for alkene hydrosilylation with the industrially relevant tertiary silane 1,1,1,3,5,5,5-heptamethyltrisiloxane (MDHM). The Co NPs demonstrated high activity when used at 30 degrees C for 3.5-7 h in toluene, with catalyst loadings 0.05-0.2 mol %, without additives. Under these mild conditions, a set of terminal alkenes were found to react with MDHM, yielding exclusively the anti-Markovnikov product in up to 99% yields. Additionally, we demonstrated the possibility of using UV irradiation to further activate these cobalt NPs not only to enhance their catalytic performances but also to promote tandem isomerization-hydrosilylation reactions using internal alkenes, among them unsaturated fatty ester (methyl oleate), to produce linear products in up to quantitative yields.
引用
收藏
页码:11732 / 11740
页数:9
相关论文
共 50 条
  • [41] A Highly Active Cobalt Catalyst System for Kumada Biaryl Cross-Coupling
    Wu, Wenqin
    Duong, Hung A.
    SYNLETT, 2018, 29 (09) : 1199 - 1202
  • [42] Supported catalysts based on Pd-In nanoparticles for the liquid- phase hydrogenation of terminal and internal alkynes: 2. catalytic properties
    Markov, P. V.
    Bragina, G. O.
    Baeva, G. N.
    Mashkovskii, I. S.
    Rassolov, A. V.
    Yakushev, I. A.
    Vargaftik, M. N.
    Stakheev, A. Yu
    KINETICS AND CATALYSIS, 2016, 57 (05) : 625 - 631
  • [43] Terminal and Internal Olefin Epoxidation with Cobalt(II) as the Catalyst: Evidence for an Active Oxidant CoII-Acylperoxo Species
    Hyun, Min Young
    Kim, Soo Hyun
    Song, Young Joo
    Lee, Hong Gyu
    Jo, Young Dan
    Kim, Jin Hoon
    Hwang, In Hong
    Noh, Jin Young
    Kang, Juhye
    Kim, Cheal
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17): : 7307 - 7312
  • [44] A cobalt-doped iron oxide nanozyme as a highly active peroxidase for renal tumor catalytic therapy
    Wang, Yixuan
    Li, Hongjun
    Guo, Lihua
    Jiang, Qi
    Liu, Feng
    RSC ADVANCES, 2019, 9 (33) : 18815 - 18822
  • [45] Conducting Polymer-Based Electrodeless Deposition of Pt Nanoparticles and Its Catalytic Properties for Regioselective Hydrosilylation Reactions
    Shih, Hung-Hsin
    Williams, Darrick
    Mack, Nathan H.
    Wang, Hsing-Lin
    MACROMOLECULES, 2009, 42 (01) : 14 - 16
  • [46] Copper nanoparticles in click chemistry: an alternative catalytic system for the cycloaddition of terminal alkynes and azides
    Alonso, Francisco
    Moglie, Yanina
    Radivoy, Gabriel
    Yus, Miguel
    TETRAHEDRON LETTERS, 2009, 50 (20) : 2358 - 2362
  • [47] Blocking and remanence properties of weakly and highly interactive cobalt ferrite based nanoparticles
    Vieira, C. A. M.
    Gomes, R. Cabreira
    Silva, F. G.
    Dias, A. L.
    Aquino, R.
    Campos, A. F. C.
    Depeyrot, J.
    JOURNAL OF PHYSICS-CONDENSED MATTER, 2019, 31 (17)
  • [48] CuI/Dabco as a highly active catalytic system for the Heck-type reaction
    Li, JH
    Wang, DP
    Xie, Y
    TETRAHEDRON LETTERS, 2005, 46 (30) : 4941 - 4944
  • [49] Pd(OAc)2/DABCO as a highly active catalytic system for the Heck reaction
    Li, JH
    Wang, DP
    Xie, YX
    SYNTHESIS-STUTTGART, 2005, (13): : 2193 - 2197
  • [50] Highly Active Metastable Ruthenium Nanoparticles for Hydrogen Production through the Catalytic Hydrolysis of Ammonia Borane
    Abo-Hamed, Enass K.
    Pennycook, Timothy
    Vaynzof, Yana
    Toprakcioglu, Chris
    Koutsioubas, Alexandros
    Scherman, Oren A.
    SMALL, 2014, 10 (15) : 3145 - 3152