Mild Peroxidative Oxidation of Cyclohexane Catalyzed by Mono-, Di-, Tri-, Tetra- and Polynuclear Copper Triethanolamine Complexes
The mono‐, di‐, tri‐, tetra‐ and polynuclear copper(II) triethanolamine (H3tea) complexes [Cu(H2tea)(N3)] (1), [Cu2(H2tea)2(XC6H4COO)2]⋅2 H2O (X=4‐H 2a, 4‐CH3 2b, 3‐Cl 2c), [Cu3(H2tea)2(4‐OC6H4COO)2(H2O)]⋅4H2O (3), [O⊂Cu4(tea)4(BOH)4][BF4]2 (4) and [Cu2(H2tea)2{μ‐C6H4(COO)2‐1,4}n]⋅2n H2O (5), respec...
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| Published in: | Advanced synthesis & catalysis Vol. 348; no. 1-2; pp. 159 - 174 |
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| Main Authors: | , , , , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Weinheim
WILEY-VCH Verlag
01-01-2006
WILEY‐VCH Verlag |
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| Abstract | The mono‐, di‐, tri‐, tetra‐ and polynuclear copper(II) triethanolamine (H3tea) complexes [Cu(H2tea)(N3)] (1), [Cu2(H2tea)2(XC6H4COO)2]⋅2 H2O (X=4‐H 2a, 4‐CH3 2b, 3‐Cl 2c), [Cu3(H2tea)2(4‐OC6H4COO)2(H2O)]⋅4H2O (3), [O⊂Cu4(tea)4(BOH)4][BF4]2 (4) and [Cu2(H2tea)2{μ‐C6H4(COO)2‐1,4}n]⋅2n H2O (5), respectively, are highly active and selective catalysts or catalyst precursors for the peroxidative oxidation of cyclohexane, in acetonitrile, to a cyclohexanol and cyclohexanone mixture, by aqueous hydrogen peroxide in acidic medium (liquid biphasic catalysis) at room temperature and atmospheric pressure. The effects on the catalytic activity of various factors, e.g., the relative amounts of cyclohexane, oxidant, catalyst, solvent and nitric acid, reaction time, catalyst recycling and impact of both carbon‐ and oxygen‐centred radical traps (supporting mainly radical mechanisms) were investigated and allowed us to achieve yields and TONs up to ca. 39% and 380, respectively, corresponding to the most active copper systems so far reported for the oxidation of cyclohexane under mild conditions. The catalysts can be reused for recycling and, at least complex 4 maintains almost the same level of activity even after five reaction cycles. The preparation of the new complexes 1, 2b and 2c by self‐assembly at room temperature, and their full characterization by IR spectroscopy, FAB‐MS+, elemental and X‐ray diffraction structural (for 1 and 2c) analyses are also reported. |
|---|---|
| AbstractList | The mono‐, di‐, tri‐, tetra‐ and polynuclear copper(II) triethanolamine (H
3
tea) complexes [Cu(H
2
tea)(N
3
)] (
1
), [Cu
2
(H
2
tea)
2
(XC
6
H
4
COO)
2
]⋅2 H
2
O (X=4‐H
2a
, 4‐CH
3
2b
, 3‐Cl
2c
), [Cu
3
(H
2
tea)
2
(4‐OC
6
H
4
COO)
2
(H
2
O)]⋅4H
2
O (
3
), [O⊂Cu
4
(tea)
4
(BOH)
4
][BF
4
]
2
(
4
) and [Cu
2
(H
2
tea)
2
{μ‐C
6
H
4
(COO)
2
‐1,4}
n
]⋅2
n
H
2
O (
5
), respectively, are highly active and selective catalysts or catalyst precursors for the peroxidative oxidation of cyclohexane, in acetonitrile, to a cyclohexanol and cyclohexanone mixture, by aqueous hydrogen peroxide in acidic medium (liquid biphasic catalysis) at room temperature and atmospheric pressure. The effects on the catalytic activity of various factors, e.g., the relative amounts of cyclohexane, oxidant, catalyst, solvent and nitric acid, reaction time, catalyst recycling and impact of both carbon‐ and oxygen‐centred radical traps (supporting mainly radical mechanisms) were investigated and allowed us to achieve yields and TONs up to
ca.
39% and 380, respectively, corresponding to the most active copper systems so far reported for the oxidation of cyclohexane under mild conditions. The catalysts can be reused for recycling and, at least complex
4
maintains almost the same level of activity even after five reaction cycles. The preparation of the new complexes
1, 2b
and
2c
by self‐assembly at room temperature, and their full characterization by IR spectroscopy, FAB‐MS
+
, elemental and X‐ray diffraction structural (for
1
and
2c
) analyses are also reported. The mono‐, di‐, tri‐, tetra‐ and polynuclear copper(II) triethanolamine (H3tea) complexes [Cu(H2tea)(N3)] (1), [Cu2(H2tea)2(XC6H4COO)2]⋅2 H2O (X=4‐H 2a, 4‐CH3 2b, 3‐Cl 2c), [Cu3(H2tea)2(4‐OC6H4COO)2(H2O)]⋅4H2O (3), [O⊂Cu4(tea)4(BOH)4][BF4]2 (4) and [Cu2(H2tea)2{μ‐C6H4(COO)2‐1,4}n]⋅2n H2O (5), respectively, are highly active and selective catalysts or catalyst precursors for the peroxidative oxidation of cyclohexane, in acetonitrile, to a cyclohexanol and cyclohexanone mixture, by aqueous hydrogen peroxide in acidic medium (liquid biphasic catalysis) at room temperature and atmospheric pressure. The effects on the catalytic activity of various factors, e.g., the relative amounts of cyclohexane, oxidant, catalyst, solvent and nitric acid, reaction time, catalyst recycling and impact of both carbon‐ and oxygen‐centred radical traps (supporting mainly radical mechanisms) were investigated and allowed us to achieve yields and TONs up to ca. 39% and 380, respectively, corresponding to the most active copper systems so far reported for the oxidation of cyclohexane under mild conditions. The catalysts can be reused for recycling and, at least complex 4 maintains almost the same level of activity even after five reaction cycles. The preparation of the new complexes 1, 2b and 2c by self‐assembly at room temperature, and their full characterization by IR spectroscopy, FAB‐MS+, elemental and X‐ray diffraction structural (for 1 and 2c) analyses are also reported. |
| Author | Kopylovich, Maximilian N. Kirillova, Marina V. da Silva, M. Fátima C. Guedes Karabach, Evgeny Yu Kirillov, Alexander M. Haukka, Matti Pombeiro, Armando J. L. |
| Author_xml | – sequence: 1 givenname: Alexander M. surname: Kirillov fullname: Kirillov, Alexander M. organization: Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, Av. Rovisco Pais, 1049-001 Lisbon, Portugal, Fax: (+351)-21-846-4455 – sequence: 2 givenname: Maximilian N. surname: Kopylovich fullname: Kopylovich, Maximilian N. organization: Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, Av. Rovisco Pais, 1049-001 Lisbon, Portugal, Fax: (+351)-21-846-4455 – sequence: 3 givenname: Marina V. surname: Kirillova fullname: Kirillova, Marina V. organization: Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, Av. Rovisco Pais, 1049-001 Lisbon, Portugal, Fax: (+351)-21-846-4455 – sequence: 4 givenname: Evgeny Yu surname: Karabach fullname: Karabach, Evgeny Yu organization: Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, Av. Rovisco Pais, 1049-001 Lisbon, Portugal, Fax: (+351)-21-846-4455 – sequence: 5 givenname: Matti surname: Haukka fullname: Haukka, Matti organization: University of Joensuu, Department of Chemistry, P. O. Box 111, FIN-80101, Joensuu, Finland – sequence: 6 givenname: M. Fátima C. Guedes surname: da Silva fullname: da Silva, M. Fátima C. Guedes organization: Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, Av. Rovisco Pais, 1049-001 Lisbon, Portugal, Fax: (+351)-21-846-4455 – sequence: 7 givenname: Armando J. L. surname: Pombeiro fullname: Pombeiro, Armando J. L. email: pombeiro@ist.utl.pt organization: Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, Av. Rovisco Pais, 1049-001 Lisbon, Portugal, Fax: (+351)-21-846-4455 |
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| Copyright | Copyright © 2006 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Snippet | The mono‐, di‐, tri‐, tetra‐ and polynuclear copper(II) triethanolamine (H3tea) complexes [Cu(H2tea)(N3)] (1), [Cu2(H2tea)2(XC6H4COO)2]⋅2 H2O (X=4‐H 2a, 4‐CH3... The mono‐, di‐, tri‐, tetra‐ and polynuclear copper(II) triethanolamine (H 3 tea) complexes [Cu(H 2 tea)(N 3 )] ( 1 ), [Cu 2 (H 2 tea) 2 (XC 6 H 4 COO) 2 ]⋅2 H... |
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| SubjectTerms | biphasic catalysis copper complexes cyclohexane N,O ligands O ligands oxidation |
| Title | Mild Peroxidative Oxidation of Cyclohexane Catalyzed by Mono-, Di-, Tri-, Tetra- and Polynuclear Copper Triethanolamine Complexes |
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