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

Martin Jakoobi (1) , Vincent Dardun (1) , Laurent Veyre (1) , Valérie Meille (2) , Clément Camp (1) , Chloé Thieuleux (1)

1 C2P2 - Laboratoire de Chimie, Catalyse, Polymères et Procédés, R 5265
2 LGPC - Laboratoire de Génie des Procédés Catalytiques

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 MDHM (1,1,1,3,5,5,5-heptamethyltrisiloxane). The Co NPs demonstrated high activity when used at 30 °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 MD H M, 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 in order 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.

Mots clés: Colloidal catalyst; cobalt nanoparticles; alkene hydrosilylation; tertiary silanes; tandem catalysis

Domaines: Chimie; Catalyse

Martin Jakoobi, Vincent Dardun, Laurent Veyre, Valérie Meille, Clément Camp, et al.. Developing a Highly Active Catalytic System Based on Cobalt Nanoparticles for Terminal and Internal Alkene Hydrosilylation. Journal of Organic Chemistry, 2020, 85 (18), pp.11732-11740. ⟨10.1021/acs.joc.0c01439⟩. ⟨hal-02998618⟩