Catalytic olefin epoxidation with cyclopentadienyl-molybdenum complexes in room temperature ionic liquids

Fritz E. Kühn; Jin Zhao; Marta Abrantes; Wei Sun; Carlos A.M. Afonso; Luis C. Branco; Isabel S. Gonçalves; Martyn Pillinger; Carlos C. Romão

doi:10.1016/j.tetlet.2004.11.029

Catalytic olefin epoxidation with cyclopentadienyl-molybdenum complexes in room temperature ionic liquids

Fritz E. Kühn, Jin Zhao, Marta Abrantes, Wei Sun, Carlos A.M. Afonso, Luis C. Branco, Isabel S. Gonçalves, Martyn Pillinger, Carlos C. Romão

Associate Professorship of Molecular Catalysis

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

71 Scopus citations

Abstract

Complexes of the type (η ⁵-C ₅R ₅)Mo(CO) ₃X (X = Me, Cl; R = H, Me), being efficient homogeneous catalysts for the epoxidation of olefins, have been examined for their catalytic performance at 55°C in systems containing room temperature ionic liquids (RTILs) of composition [BMIM]NTf ₂, [BMIM]PF ₆, [C ₈MIM] PF ₆ and [BMIM]BF ₄. The catalytic performance for cyclooctene epoxidation depends strongly on the water content of the system, the catalyst solubility in the RTIL, and the reaction behaviour of the RTIL under the applied reaction conditions. The catalysts can be recycled without significant loss of activity when a reaction system containing [BMIM]NTf ₂ and [BMIM]PF ₆ in a 4:1 relationship is used. High proportions of [BMIM]PF ₆ lead to a ring opening reaction (diol formation), due to HF formation and the presence of residual water.

Original language	English
Pages (from-to)	47-52
Number of pages	6
Journal	Tetrahedron Letters
Volume	46
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2004.11.029
State	Published - 3 Jan 2005

Keywords

Catalysis
Cyclopentadienyl
Ionic liquids
Molybdenum
Olefin epoxidation

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10.1016/j.tetlet.2004.11.029

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title = "Catalytic olefin epoxidation with cyclopentadienyl-molybdenum complexes in room temperature ionic liquids",

abstract = "Complexes of the type (η 5-C 5R 5)Mo(CO) 3X (X = Me, Cl; R = H, Me), being efficient homogeneous catalysts for the epoxidation of olefins, have been examined for their catalytic performance at 55°C in systems containing room temperature ionic liquids (RTILs) of composition [BMIM]NTf 2, [BMIM]PF 6, [C 8MIM] PF 6 and [BMIM]BF 4. The catalytic performance for cyclooctene epoxidation depends strongly on the water content of the system, the catalyst solubility in the RTIL, and the reaction behaviour of the RTIL under the applied reaction conditions. The catalysts can be recycled without significant loss of activity when a reaction system containing [BMIM]NTf 2 and [BMIM]PF 6 in a 4:1 relationship is used. High proportions of [BMIM]PF 6 lead to a ring opening reaction (diol formation), due to HF formation and the presence of residual water.",

keywords = "Catalysis, Cyclopentadienyl, Ionic liquids, Molybdenum, Olefin epoxidation",

author = "K{\"u}hn, {Fritz E.} and Jin Zhao and Marta Abrantes and Wei Sun and Afonso, {Carlos A.M.} and Branco, {Luis C.} and Gon{\c c}alves, {Isabel S.} and Martyn Pillinger and Rom{\~a}o, {Carlos C.}",

year = "2005",

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doi = "10.1016/j.tetlet.2004.11.029",

language = "English",

volume = "46",

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journal = "Tetrahedron Letters",

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T1 - Catalytic olefin epoxidation with cyclopentadienyl-molybdenum complexes in room temperature ionic liquids

AU - Kühn, Fritz E.

AU - Zhao, Jin

AU - Abrantes, Marta

AU - Sun, Wei

AU - Afonso, Carlos A.M.

AU - Branco, Luis C.

AU - Gonçalves, Isabel S.

AU - Pillinger, Martyn

AU - Romão, Carlos C.

PY - 2005/1/3

Y1 - 2005/1/3

N2 - Complexes of the type (η 5-C 5R 5)Mo(CO) 3X (X = Me, Cl; R = H, Me), being efficient homogeneous catalysts for the epoxidation of olefins, have been examined for their catalytic performance at 55°C in systems containing room temperature ionic liquids (RTILs) of composition [BMIM]NTf 2, [BMIM]PF 6, [C 8MIM] PF 6 and [BMIM]BF 4. The catalytic performance for cyclooctene epoxidation depends strongly on the water content of the system, the catalyst solubility in the RTIL, and the reaction behaviour of the RTIL under the applied reaction conditions. The catalysts can be recycled without significant loss of activity when a reaction system containing [BMIM]NTf 2 and [BMIM]PF 6 in a 4:1 relationship is used. High proportions of [BMIM]PF 6 lead to a ring opening reaction (diol formation), due to HF formation and the presence of residual water.

AB - Complexes of the type (η 5-C 5R 5)Mo(CO) 3X (X = Me, Cl; R = H, Me), being efficient homogeneous catalysts for the epoxidation of olefins, have been examined for their catalytic performance at 55°C in systems containing room temperature ionic liquids (RTILs) of composition [BMIM]NTf 2, [BMIM]PF 6, [C 8MIM] PF 6 and [BMIM]BF 4. The catalytic performance for cyclooctene epoxidation depends strongly on the water content of the system, the catalyst solubility in the RTIL, and the reaction behaviour of the RTIL under the applied reaction conditions. The catalysts can be recycled without significant loss of activity when a reaction system containing [BMIM]NTf 2 and [BMIM]PF 6 in a 4:1 relationship is used. High proportions of [BMIM]PF 6 lead to a ring opening reaction (diol formation), due to HF formation and the presence of residual water.

KW - Catalysis

KW - Cyclopentadienyl

KW - Ionic liquids

KW - Molybdenum

KW - Olefin epoxidation

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DO - 10.1016/j.tetlet.2004.11.029

M3 - Article

AN - SCOPUS:9944235034

SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 1

ER -

Catalytic olefin epoxidation with cyclopentadienyl-molybdenum complexes in room temperature ionic liquids

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Keywords

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