Modified cobalt(II) acetylacetonate complexes as catalysts for Negishi-type coupling reactions: influence of ligand electronic properties on catalyst activity
Abstract Four known electronically diverse cobalt(II) acetylacetonate derivatives were synthesized by replacement of the acetylacetonate methyl groups with combinations of tert-butyl, ethoxy, and trifluoromethyl groups in order to study the effect of catalyst electronic properties on the reaction ra...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Struzinski, Tyler H. [verfasserIn] |
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| Format: |
Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2009 |
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| Schlagwörter: |
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| Anmerkung: |
© Springer Science+Business Media B.V. 2009 |
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| Übergeordnetes Werk: |
Enthalten in: Transition metal chemistry - Springer Netherlands, 1975, 34(2009), 6 vom: 26. Juni, Seite 637-640 |
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| Übergeordnetes Werk: |
volume:34 ; year:2009 ; number:6 ; day:26 ; month:06 ; pages:637-640 |
| Links: |
|---|
| DOI / URN: |
10.1007/s11243-009-9241-9 |
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OLC2084039215 |
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| 520 | |a Abstract Four known electronically diverse cobalt(II) acetylacetonate derivatives were synthesized by replacement of the acetylacetonate methyl groups with combinations of tert-butyl, ethoxy, and trifluoromethyl groups in order to study the effect of catalyst electronic properties on the reaction rate and product yield of the cobalt-catalyzed reaction between haloalkenes and butylzinc iodide. Infrared spectroscopy of these compounds showed an increase in the CO stretching frequency as the ligand substituents became more electron withdrawing. These compounds, in addition to cobalt(II) acetylacetonate itself, were evaluated as catalysts for the coupling reaction between (E)-1-iodo-1-octene and butylzinc iodide to form (E)-5-dodecene. Faster reaction rates were observed and higher yields of 5-dodecene were produced when catalysts containing electron-donating ligands were employed. Side reactions, including the homocoupling of 1-iodo-1-octene to produce 7,9-hexadecadiene, were also observed under the reported reaction conditions. The rate of side-product formation was more competitive with the rate of the cross-coupling reaction when slower, electron-deficient catalysts were employed. | ||
| 650 | 4 | |a Acac | |
| 650 | 4 | |a Acetylacetonate | |
| 650 | 4 | |a Ethyl Acetoacetate | |
| 650 | 4 | |a Cobalt Acetate | |
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| 700 | 1 | |a von Gohren, Lydia R. |4 aut | |
| 700 | 1 | |a Roy MacArthur, Amy H. |4 aut | |
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10.1007/s11243-009-9241-9 doi (DE-627)OLC2084039215 (DE-He213)s11243-009-9241-9-p DE-627 ger DE-627 rakwb eng 660 VZ Struzinski, Tyler H. verfasserin aut Modified cobalt(II) acetylacetonate complexes as catalysts for Negishi-type coupling reactions: influence of ligand electronic properties on catalyst activity 2009 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © Springer Science+Business Media B.V. 2009 Abstract Four known electronically diverse cobalt(II) acetylacetonate derivatives were synthesized by replacement of the acetylacetonate methyl groups with combinations of tert-butyl, ethoxy, and trifluoromethyl groups in order to study the effect of catalyst electronic properties on the reaction rate and product yield of the cobalt-catalyzed reaction between haloalkenes and butylzinc iodide. Infrared spectroscopy of these compounds showed an increase in the CO stretching frequency as the ligand substituents became more electron withdrawing. These compounds, in addition to cobalt(II) acetylacetonate itself, were evaluated as catalysts for the coupling reaction between (E)-1-iodo-1-octene and butylzinc iodide to form (E)-5-dodecene. Faster reaction rates were observed and higher yields of 5-dodecene were produced when catalysts containing electron-donating ligands were employed. Side reactions, including the homocoupling of 1-iodo-1-octene to produce 7,9-hexadecadiene, were also observed under the reported reaction conditions. The rate of side-product formation was more competitive with the rate of the cross-coupling reaction when slower, electron-deficient catalysts were employed. Acac Acetylacetonate Ethyl Acetoacetate Cobalt Acetate Allyl Acetate von Gohren, Lydia R. aut Roy MacArthur, Amy H. aut Enthalten in Transition metal chemistry Springer Netherlands, 1975 34(2009), 6 vom: 26. Juni, Seite 637-640 (DE-627)129605417 (DE-600)242084-3 (DE-576)015099652 0340-4285 nnns volume:34 year:2009 number:6 day:26 month:06 pages:637-640 https://doi.org/10.1007/s11243-009-9241-9 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE GBV_ILN_21 GBV_ILN_70 GBV_ILN_4012 GBV_ILN_4125 AR 34 2009 6 26 06 637-640 |
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10.1007/s11243-009-9241-9 doi (DE-627)OLC2084039215 (DE-He213)s11243-009-9241-9-p DE-627 ger DE-627 rakwb eng 660 VZ Struzinski, Tyler H. verfasserin aut Modified cobalt(II) acetylacetonate complexes as catalysts for Negishi-type coupling reactions: influence of ligand electronic properties on catalyst activity 2009 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © Springer Science+Business Media B.V. 2009 Abstract Four known electronically diverse cobalt(II) acetylacetonate derivatives were synthesized by replacement of the acetylacetonate methyl groups with combinations of tert-butyl, ethoxy, and trifluoromethyl groups in order to study the effect of catalyst electronic properties on the reaction rate and product yield of the cobalt-catalyzed reaction between haloalkenes and butylzinc iodide. Infrared spectroscopy of these compounds showed an increase in the CO stretching frequency as the ligand substituents became more electron withdrawing. These compounds, in addition to cobalt(II) acetylacetonate itself, were evaluated as catalysts for the coupling reaction between (E)-1-iodo-1-octene and butylzinc iodide to form (E)-5-dodecene. Faster reaction rates were observed and higher yields of 5-dodecene were produced when catalysts containing electron-donating ligands were employed. Side reactions, including the homocoupling of 1-iodo-1-octene to produce 7,9-hexadecadiene, were also observed under the reported reaction conditions. The rate of side-product formation was more competitive with the rate of the cross-coupling reaction when slower, electron-deficient catalysts were employed. Acac Acetylacetonate Ethyl Acetoacetate Cobalt Acetate Allyl Acetate von Gohren, Lydia R. aut Roy MacArthur, Amy H. aut Enthalten in Transition metal chemistry Springer Netherlands, 1975 34(2009), 6 vom: 26. Juni, Seite 637-640 (DE-627)129605417 (DE-600)242084-3 (DE-576)015099652 0340-4285 nnns volume:34 year:2009 number:6 day:26 month:06 pages:637-640 https://doi.org/10.1007/s11243-009-9241-9 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE GBV_ILN_21 GBV_ILN_70 GBV_ILN_4012 GBV_ILN_4125 AR 34 2009 6 26 06 637-640 |
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10.1007/s11243-009-9241-9 doi (DE-627)OLC2084039215 (DE-He213)s11243-009-9241-9-p DE-627 ger DE-627 rakwb eng 660 VZ Struzinski, Tyler H. verfasserin aut Modified cobalt(II) acetylacetonate complexes as catalysts for Negishi-type coupling reactions: influence of ligand electronic properties on catalyst activity 2009 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © Springer Science+Business Media B.V. 2009 Abstract Four known electronically diverse cobalt(II) acetylacetonate derivatives were synthesized by replacement of the acetylacetonate methyl groups with combinations of tert-butyl, ethoxy, and trifluoromethyl groups in order to study the effect of catalyst electronic properties on the reaction rate and product yield of the cobalt-catalyzed reaction between haloalkenes and butylzinc iodide. Infrared spectroscopy of these compounds showed an increase in the CO stretching frequency as the ligand substituents became more electron withdrawing. These compounds, in addition to cobalt(II) acetylacetonate itself, were evaluated as catalysts for the coupling reaction between (E)-1-iodo-1-octene and butylzinc iodide to form (E)-5-dodecene. Faster reaction rates were observed and higher yields of 5-dodecene were produced when catalysts containing electron-donating ligands were employed. Side reactions, including the homocoupling of 1-iodo-1-octene to produce 7,9-hexadecadiene, were also observed under the reported reaction conditions. The rate of side-product formation was more competitive with the rate of the cross-coupling reaction when slower, electron-deficient catalysts were employed. Acac Acetylacetonate Ethyl Acetoacetate Cobalt Acetate Allyl Acetate von Gohren, Lydia R. aut Roy MacArthur, Amy H. aut Enthalten in Transition metal chemistry Springer Netherlands, 1975 34(2009), 6 vom: 26. Juni, Seite 637-640 (DE-627)129605417 (DE-600)242084-3 (DE-576)015099652 0340-4285 nnns volume:34 year:2009 number:6 day:26 month:06 pages:637-640 https://doi.org/10.1007/s11243-009-9241-9 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE GBV_ILN_21 GBV_ILN_70 GBV_ILN_4012 GBV_ILN_4125 AR 34 2009 6 26 06 637-640 |
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10.1007/s11243-009-9241-9 doi (DE-627)OLC2084039215 (DE-He213)s11243-009-9241-9-p DE-627 ger DE-627 rakwb eng 660 VZ Struzinski, Tyler H. verfasserin aut Modified cobalt(II) acetylacetonate complexes as catalysts for Negishi-type coupling reactions: influence of ligand electronic properties on catalyst activity 2009 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © Springer Science+Business Media B.V. 2009 Abstract Four known electronically diverse cobalt(II) acetylacetonate derivatives were synthesized by replacement of the acetylacetonate methyl groups with combinations of tert-butyl, ethoxy, and trifluoromethyl groups in order to study the effect of catalyst electronic properties on the reaction rate and product yield of the cobalt-catalyzed reaction between haloalkenes and butylzinc iodide. Infrared spectroscopy of these compounds showed an increase in the CO stretching frequency as the ligand substituents became more electron withdrawing. These compounds, in addition to cobalt(II) acetylacetonate itself, were evaluated as catalysts for the coupling reaction between (E)-1-iodo-1-octene and butylzinc iodide to form (E)-5-dodecene. Faster reaction rates were observed and higher yields of 5-dodecene were produced when catalysts containing electron-donating ligands were employed. Side reactions, including the homocoupling of 1-iodo-1-octene to produce 7,9-hexadecadiene, were also observed under the reported reaction conditions. The rate of side-product formation was more competitive with the rate of the cross-coupling reaction when slower, electron-deficient catalysts were employed. Acac Acetylacetonate Ethyl Acetoacetate Cobalt Acetate Allyl Acetate von Gohren, Lydia R. aut Roy MacArthur, Amy H. aut Enthalten in Transition metal chemistry Springer Netherlands, 1975 34(2009), 6 vom: 26. Juni, Seite 637-640 (DE-627)129605417 (DE-600)242084-3 (DE-576)015099652 0340-4285 nnns volume:34 year:2009 number:6 day:26 month:06 pages:637-640 https://doi.org/10.1007/s11243-009-9241-9 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE GBV_ILN_21 GBV_ILN_70 GBV_ILN_4012 GBV_ILN_4125 AR 34 2009 6 26 06 637-640 |
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10.1007/s11243-009-9241-9 doi (DE-627)OLC2084039215 (DE-He213)s11243-009-9241-9-p DE-627 ger DE-627 rakwb eng 660 VZ Struzinski, Tyler H. verfasserin aut Modified cobalt(II) acetylacetonate complexes as catalysts for Negishi-type coupling reactions: influence of ligand electronic properties on catalyst activity 2009 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © Springer Science+Business Media B.V. 2009 Abstract Four known electronically diverse cobalt(II) acetylacetonate derivatives were synthesized by replacement of the acetylacetonate methyl groups with combinations of tert-butyl, ethoxy, and trifluoromethyl groups in order to study the effect of catalyst electronic properties on the reaction rate and product yield of the cobalt-catalyzed reaction between haloalkenes and butylzinc iodide. Infrared spectroscopy of these compounds showed an increase in the CO stretching frequency as the ligand substituents became more electron withdrawing. These compounds, in addition to cobalt(II) acetylacetonate itself, were evaluated as catalysts for the coupling reaction between (E)-1-iodo-1-octene and butylzinc iodide to form (E)-5-dodecene. Faster reaction rates were observed and higher yields of 5-dodecene were produced when catalysts containing electron-donating ligands were employed. Side reactions, including the homocoupling of 1-iodo-1-octene to produce 7,9-hexadecadiene, were also observed under the reported reaction conditions. The rate of side-product formation was more competitive with the rate of the cross-coupling reaction when slower, electron-deficient catalysts were employed. Acac Acetylacetonate Ethyl Acetoacetate Cobalt Acetate Allyl Acetate von Gohren, Lydia R. aut Roy MacArthur, Amy H. aut Enthalten in Transition metal chemistry Springer Netherlands, 1975 34(2009), 6 vom: 26. Juni, Seite 637-640 (DE-627)129605417 (DE-600)242084-3 (DE-576)015099652 0340-4285 nnns volume:34 year:2009 number:6 day:26 month:06 pages:637-640 https://doi.org/10.1007/s11243-009-9241-9 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE GBV_ILN_21 GBV_ILN_70 GBV_ILN_4012 GBV_ILN_4125 AR 34 2009 6 26 06 637-640 |
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Struzinski, Tyler H. |
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Struzinski, Tyler H. ddc 660 misc Acac misc Acetylacetonate misc Ethyl Acetoacetate misc Cobalt Acetate misc Allyl Acetate Modified cobalt(II) acetylacetonate complexes as catalysts for Negishi-type coupling reactions: influence of ligand electronic properties on catalyst activity |
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| title_sort |
modified cobalt(ii) acetylacetonate complexes as catalysts for negishi-type coupling reactions: influence of ligand electronic properties on catalyst activity |
| title_auth |
Modified cobalt(II) acetylacetonate complexes as catalysts for Negishi-type coupling reactions: influence of ligand electronic properties on catalyst activity |
| abstract |
Abstract Four known electronically diverse cobalt(II) acetylacetonate derivatives were synthesized by replacement of the acetylacetonate methyl groups with combinations of tert-butyl, ethoxy, and trifluoromethyl groups in order to study the effect of catalyst electronic properties on the reaction rate and product yield of the cobalt-catalyzed reaction between haloalkenes and butylzinc iodide. Infrared spectroscopy of these compounds showed an increase in the CO stretching frequency as the ligand substituents became more electron withdrawing. These compounds, in addition to cobalt(II) acetylacetonate itself, were evaluated as catalysts for the coupling reaction between (E)-1-iodo-1-octene and butylzinc iodide to form (E)-5-dodecene. Faster reaction rates were observed and higher yields of 5-dodecene were produced when catalysts containing electron-donating ligands were employed. Side reactions, including the homocoupling of 1-iodo-1-octene to produce 7,9-hexadecadiene, were also observed under the reported reaction conditions. The rate of side-product formation was more competitive with the rate of the cross-coupling reaction when slower, electron-deficient catalysts were employed. © Springer Science+Business Media B.V. 2009 |
| abstractGer |
Abstract Four known electronically diverse cobalt(II) acetylacetonate derivatives were synthesized by replacement of the acetylacetonate methyl groups with combinations of tert-butyl, ethoxy, and trifluoromethyl groups in order to study the effect of catalyst electronic properties on the reaction rate and product yield of the cobalt-catalyzed reaction between haloalkenes and butylzinc iodide. Infrared spectroscopy of these compounds showed an increase in the CO stretching frequency as the ligand substituents became more electron withdrawing. These compounds, in addition to cobalt(II) acetylacetonate itself, were evaluated as catalysts for the coupling reaction between (E)-1-iodo-1-octene and butylzinc iodide to form (E)-5-dodecene. Faster reaction rates were observed and higher yields of 5-dodecene were produced when catalysts containing electron-donating ligands were employed. Side reactions, including the homocoupling of 1-iodo-1-octene to produce 7,9-hexadecadiene, were also observed under the reported reaction conditions. The rate of side-product formation was more competitive with the rate of the cross-coupling reaction when slower, electron-deficient catalysts were employed. © Springer Science+Business Media B.V. 2009 |
| abstract_unstemmed |
Abstract Four known electronically diverse cobalt(II) acetylacetonate derivatives were synthesized by replacement of the acetylacetonate methyl groups with combinations of tert-butyl, ethoxy, and trifluoromethyl groups in order to study the effect of catalyst electronic properties on the reaction rate and product yield of the cobalt-catalyzed reaction between haloalkenes and butylzinc iodide. Infrared spectroscopy of these compounds showed an increase in the CO stretching frequency as the ligand substituents became more electron withdrawing. These compounds, in addition to cobalt(II) acetylacetonate itself, were evaluated as catalysts for the coupling reaction between (E)-1-iodo-1-octene and butylzinc iodide to form (E)-5-dodecene. Faster reaction rates were observed and higher yields of 5-dodecene were produced when catalysts containing electron-donating ligands were employed. Side reactions, including the homocoupling of 1-iodo-1-octene to produce 7,9-hexadecadiene, were also observed under the reported reaction conditions. The rate of side-product formation was more competitive with the rate of the cross-coupling reaction when slower, electron-deficient catalysts were employed. © Springer Science+Business Media B.V. 2009 |
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| container_issue |
6 |
| title_short |
Modified cobalt(II) acetylacetonate complexes as catalysts for Negishi-type coupling reactions: influence of ligand electronic properties on catalyst activity |
| url |
https://doi.org/10.1007/s11243-009-9241-9 |
| remote_bool |
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| author2 |
von Gohren, Lydia R. Roy MacArthur, Amy H. |
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2024-07-04T01:17:45.671Z |
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