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
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