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

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

doi:10.1039/c0dt00760a

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

Sarim Dastgir^*
, Karl S. Coleman
, Malcolm L.H. Green

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

52 Citations (Scopus)

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 (tmp^tBu)HI (3b), respectively, have been synthesised. The palladium(ii) complexes (η³-C ₃H₅) (tmpMes)PdCl (5a) and (η³-C ₃H₅)(tmp^tBu)PdCl (5b), rhodium(i) and iridium(i) complexes (η⁴-1,5-COD) (tmpMes)MCl, M = Rh (6a), Ir (7a) and (η⁴-1,5-COD)(tmp^tBu)MCl, where M = Rh (6b), Ir (7b), were synthesised by silver transmetallation reactions using the silver(i) complexes (tmpMes)AgI (4a) and (tmp^tBu)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.

Original language	English
Pages (from-to)	661-672
Number of pages	12
Journal	Dalton Transactions
Volume	40
Issue number	3
DOIs	https://doi.org/10.1039/c0dt00760a
Publication status	Published - 21 Jan 2011
Externally published	Yes

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title = "Heterogenised N-heterocyclic carbene complexes: Synthesis, characterisation and application for hydroformylation and C-C bond formation reactions",

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 (η3-C 3H5) (tmpMes)PdCl (5a) and (η3-C 3H5)(tmptBu)PdCl (5b), rhodium(i) and iridium(i) complexes (η4-1,5-COD) (tmpMes)MCl, M = Rh (6a), Ir (7a) and (η4-1,5-COD)(tmptBu)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.",

author = "Sarim Dastgir and Coleman, \{Karl S.\} and Green, \{Malcolm L.H.\}",

year = "2011",

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doi = "10.1039/c0dt00760a",

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T1 - Heterogenised N-heterocyclic carbene complexes

T2 - Synthesis, characterisation and application for hydroformylation and C-C bond formation reactions

AU - Dastgir, Sarim

AU - Coleman, Karl S.

AU - Green, Malcolm L.H.

PY - 2011/1/21

Y1 - 2011/1/21

N2 - 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 (η3-C 3H5) (tmpMes)PdCl (5a) and (η3-C 3H5)(tmptBu)PdCl (5b), rhodium(i) and iridium(i) complexes (η4-1,5-COD) (tmpMes)MCl, M = Rh (6a), Ir (7a) and (η4-1,5-COD)(tmptBu)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.

AB - 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 (η3-C 3H5) (tmpMes)PdCl (5a) and (η3-C 3H5)(tmptBu)PdCl (5b), rhodium(i) and iridium(i) complexes (η4-1,5-COD) (tmpMes)MCl, M = Rh (6a), Ir (7a) and (η4-1,5-COD)(tmptBu)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.

UR - https://www.scopus.com/pages/publications/78650717730

U2 - 10.1039/c0dt00760a

DO - 10.1039/c0dt00760a

M3 - Article

AN - SCOPUS:78650717730

SN - 1477-9226

VL - 40

SP - 661

EP - 672

JO - Dalton Transactions

JF - Dalton Transactions

IS - 3

ER -

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

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