Heterogenised N-heterocyclic carbene complexes: synthesis, characterisation and application for hydroformylation and C-C bond formation reactions

Dastgir, Sarim; Coleman, Karl S.; Green, Malcolm L.H.

Abstract

The imidazolium salts: 1-mesityl-3-(3-trimethoxysilylpropyl) imidazolium iodide and 1-tert-butyl-3-(3-trimethoxysilylpropyl) imidazolium iodide, abbreviated as (tmpMes)HI (3a) and (tmptBu)HI (3b), respectively, have been synthesised. The palladium(II) complexes (eta(3)-C3H5) (tmpMes) PdCl (5a) and (eta(3)-C3H5)(tmp(t)Bu)PdCl (5b), rhodium(I) and iridium(I) complexes (eta(4)-1,5-COD) (tmpMes)MCl, M = Rh (6a), Ir (7a) and (eta 4-1,5-COD)(tmp(t)Bu)MCl, where M = Rh (6b), Ir (7b), were synthesised by silver transmetallation reactions using the silver(I) complexes (tmpMes)AgI (4a) and (tmptBu) AgI (4b). The iridium complex 7b has been structurally characterised. The Pd(II) and Rh(I) complexes have been immobilised by attachment to chemically modified MCM-41. The immobilised palladium(II) materials have been tested as recyclable catalysts for Suzuki type C-C bond formation reactions in water and the immobilised rhodium(I) materials have been examined for their catalytic ability for the hydroformylation of 1-octene.

Citation

Dastgir, S., Coleman, K. S., & Green, M. L. (2011). Heterogenised N-heterocyclic carbene complexes: synthesis, characterisation and application for hydroformylation and C-C bond formation reactions. Dalton Transactions, 40(3), 661-672. https://doi.org/10.1039/c0dt00760a

• Journal Article Type: Article
• Publication Date: 2011
• Deposit Date: May 21, 2014
• Journal: Dalton Transactions
• Print ISSN: 1477-9226
• Electronic ISSN: 1477-9234
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 40
• Issue: 3
• Pages: 661-672
• DOI: https://doi.org/10.1039/c0dt00760a
• Keywords: cross-coupling reactions supported palladium catalyst transition-metal-complexes sigma-allylic complexes x-ray-structure molecular-sieves organometallic catalysis iridium complexes rhodium complexes chiral catalysts