Palladium Nanoparticles from Different Reducing Systems as Heck Catalysts
Palladium(0) nanoparticles have been widely used in cross coupling reactions, including Heck reactions. For this study, we synthesized palladium(0) nanoparticles in colloidal suspension using different combinations of solvents and reducing methods under aerobic conditions. The variation in systems u...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Redón, Rocío [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2021 |
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| Schlagwörter: |
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| Anmerkung: |
© The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2021 |
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| Übergeordnetes Werk: |
Enthalten in: Catalysis letters - Dordrecht [u.a.] : Springer Science + Business Media B.V, 1988, 152(2021), 1 vom: 07. Apr., Seite 151-161 |
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| Übergeordnetes Werk: |
volume:152 ; year:2021 ; number:1 ; day:07 ; month:04 ; pages:151-161 |
| Links: |
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| DOI / URN: |
10.1007/s10562-021-03613-9 |
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SPR045935092 |
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| 520 | |a Palladium(0) nanoparticles have been widely used in cross coupling reactions, including Heck reactions. For this study, we synthesized palladium(0) nanoparticles in colloidal suspension using different combinations of solvents and reducing methods under aerobic conditions. The variation in systems used to synthesize palladium(0) nanoparticles resulted in different nanoparticle sizes. To investigate whether the particle size had an effect on catalysis, we first used common Heck C–C cross-coupling reaction conditions (200 °C and 18 h). In addition, we omitted the use of stabilizing agents, other than the solvent and/or the anions in the initial nanoparticle synthesis, since the use of stabilizing agents adds cost and processing time to catalysis. All of the catalysts investigated worked in the cross coupling C–C Heck reaction, but yields did not show appreciable differences, as high temperature and long reaction times promote a high reduction of palladium(II). Therefore, we decided to work with a temperature and reaction time in which conversion would start to be observed (minimum reaction conditions). The experiments to determine minimum reaction conditions showed that this would be 120 °C and 10 h, therefore we used these conditions in Heck C–C cross-coupling reactions and all the palladium nanoparticle systems. The best C–C catalysis conversion was observed when N,N-dimethylformamide was used as solvent in the absence of reducing agent. This catalyst system resulted in the largest possible nanoparticles, which were kept in dispersion (did not precipitate out), showing that size is important in obtaining good yields in C–C Heck catalysis (where cocktail-type catalysis could explain the conversion). Nanoparticles of this size also act as a reservoir of soluble palladium species that behave as the true catalyst. The second best conversion was observed in N,N-dimethylformamide with sodium citrate, where citrate may have added extra protection, and since the palladium(0) nanoparticles were small, cocktail-type catalysis was not involved in obtaining high yields. Graphic Abstract | ||
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| 650 | 4 | |a Nanoparticle size |7 (dpeaa)DE-He213 | |
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10.1007/s10562-021-03613-9 doi (DE-627)SPR045935092 (SPR)s10562-021-03613-9-e DE-627 ger DE-627 rakwb eng Redón, Rocío verfasserin (orcid)0000-0001-8691-8020 aut Palladium Nanoparticles from Different Reducing Systems as Heck Catalysts 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2021 Palladium(0) nanoparticles have been widely used in cross coupling reactions, including Heck reactions. For this study, we synthesized palladium(0) nanoparticles in colloidal suspension using different combinations of solvents and reducing methods under aerobic conditions. The variation in systems used to synthesize palladium(0) nanoparticles resulted in different nanoparticle sizes. To investigate whether the particle size had an effect on catalysis, we first used common Heck C–C cross-coupling reaction conditions (200 °C and 18 h). In addition, we omitted the use of stabilizing agents, other than the solvent and/or the anions in the initial nanoparticle synthesis, since the use of stabilizing agents adds cost and processing time to catalysis. All of the catalysts investigated worked in the cross coupling C–C Heck reaction, but yields did not show appreciable differences, as high temperature and long reaction times promote a high reduction of palladium(II). Therefore, we decided to work with a temperature and reaction time in which conversion would start to be observed (minimum reaction conditions). The experiments to determine minimum reaction conditions showed that this would be 120 °C and 10 h, therefore we used these conditions in Heck C–C cross-coupling reactions and all the palladium nanoparticle systems. The best C–C catalysis conversion was observed when N,N-dimethylformamide was used as solvent in the absence of reducing agent. This catalyst system resulted in the largest possible nanoparticles, which were kept in dispersion (did not precipitate out), showing that size is important in obtaining good yields in C–C Heck catalysis (where cocktail-type catalysis could explain the conversion). Nanoparticles of this size also act as a reservoir of soluble palladium species that behave as the true catalyst. The second best conversion was observed in N,N-dimethylformamide with sodium citrate, where citrate may have added extra protection, and since the palladium(0) nanoparticles were small, cocktail-type catalysis was not involved in obtaining high yields. Graphic Abstract Palladium nanoparticles (dpeaa)DE-He213 Nanoparticle size (dpeaa)DE-He213 Heck C–C cross-coupling reactions (dpeaa)DE-He213 Palladium reduction (dpeaa)DE-He213 González-García, Tania (orcid)0000-0003-2221-0319 aut Espinoza-Flores, Lorena aut Reyes-Mosso, Alfonsina (orcid)0000-0003-4473-0198 aut Martin, Erika aut Ugalde-Saldivar, V. M. (orcid)0000-0002-9625-8713 aut Enthalten in Catalysis letters Dordrecht [u.a.] : Springer Science + Business Media B.V, 1988 152(2021), 1 vom: 07. Apr., Seite 151-161 (DE-627)306717638 (DE-600)1501518-X 1572-879X nnns volume:152 year:2021 number:1 day:07 month:04 pages:151-161 https://dx.doi.org/10.1007/s10562-021-03613-9 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 152 2021 1 07 04 151-161 |
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10.1007/s10562-021-03613-9 doi (DE-627)SPR045935092 (SPR)s10562-021-03613-9-e DE-627 ger DE-627 rakwb eng Redón, Rocío verfasserin (orcid)0000-0001-8691-8020 aut Palladium Nanoparticles from Different Reducing Systems as Heck Catalysts 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2021 Palladium(0) nanoparticles have been widely used in cross coupling reactions, including Heck reactions. For this study, we synthesized palladium(0) nanoparticles in colloidal suspension using different combinations of solvents and reducing methods under aerobic conditions. The variation in systems used to synthesize palladium(0) nanoparticles resulted in different nanoparticle sizes. To investigate whether the particle size had an effect on catalysis, we first used common Heck C–C cross-coupling reaction conditions (200 °C and 18 h). In addition, we omitted the use of stabilizing agents, other than the solvent and/or the anions in the initial nanoparticle synthesis, since the use of stabilizing agents adds cost and processing time to catalysis. All of the catalysts investigated worked in the cross coupling C–C Heck reaction, but yields did not show appreciable differences, as high temperature and long reaction times promote a high reduction of palladium(II). Therefore, we decided to work with a temperature and reaction time in which conversion would start to be observed (minimum reaction conditions). The experiments to determine minimum reaction conditions showed that this would be 120 °C and 10 h, therefore we used these conditions in Heck C–C cross-coupling reactions and all the palladium nanoparticle systems. The best C–C catalysis conversion was observed when N,N-dimethylformamide was used as solvent in the absence of reducing agent. This catalyst system resulted in the largest possible nanoparticles, which were kept in dispersion (did not precipitate out), showing that size is important in obtaining good yields in C–C Heck catalysis (where cocktail-type catalysis could explain the conversion). Nanoparticles of this size also act as a reservoir of soluble palladium species that behave as the true catalyst. The second best conversion was observed in N,N-dimethylformamide with sodium citrate, where citrate may have added extra protection, and since the palladium(0) nanoparticles were small, cocktail-type catalysis was not involved in obtaining high yields. Graphic Abstract Palladium nanoparticles (dpeaa)DE-He213 Nanoparticle size (dpeaa)DE-He213 Heck C–C cross-coupling reactions (dpeaa)DE-He213 Palladium reduction (dpeaa)DE-He213 González-García, Tania (orcid)0000-0003-2221-0319 aut Espinoza-Flores, Lorena aut Reyes-Mosso, Alfonsina (orcid)0000-0003-4473-0198 aut Martin, Erika aut Ugalde-Saldivar, V. M. (orcid)0000-0002-9625-8713 aut Enthalten in Catalysis letters Dordrecht [u.a.] : Springer Science + Business Media B.V, 1988 152(2021), 1 vom: 07. Apr., Seite 151-161 (DE-627)306717638 (DE-600)1501518-X 1572-879X nnns volume:152 year:2021 number:1 day:07 month:04 pages:151-161 https://dx.doi.org/10.1007/s10562-021-03613-9 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 152 2021 1 07 04 151-161 |
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10.1007/s10562-021-03613-9 doi (DE-627)SPR045935092 (SPR)s10562-021-03613-9-e DE-627 ger DE-627 rakwb eng Redón, Rocío verfasserin (orcid)0000-0001-8691-8020 aut Palladium Nanoparticles from Different Reducing Systems as Heck Catalysts 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2021 Palladium(0) nanoparticles have been widely used in cross coupling reactions, including Heck reactions. For this study, we synthesized palladium(0) nanoparticles in colloidal suspension using different combinations of solvents and reducing methods under aerobic conditions. The variation in systems used to synthesize palladium(0) nanoparticles resulted in different nanoparticle sizes. To investigate whether the particle size had an effect on catalysis, we first used common Heck C–C cross-coupling reaction conditions (200 °C and 18 h). In addition, we omitted the use of stabilizing agents, other than the solvent and/or the anions in the initial nanoparticle synthesis, since the use of stabilizing agents adds cost and processing time to catalysis. All of the catalysts investigated worked in the cross coupling C–C Heck reaction, but yields did not show appreciable differences, as high temperature and long reaction times promote a high reduction of palladium(II). Therefore, we decided to work with a temperature and reaction time in which conversion would start to be observed (minimum reaction conditions). The experiments to determine minimum reaction conditions showed that this would be 120 °C and 10 h, therefore we used these conditions in Heck C–C cross-coupling reactions and all the palladium nanoparticle systems. The best C–C catalysis conversion was observed when N,N-dimethylformamide was used as solvent in the absence of reducing agent. This catalyst system resulted in the largest possible nanoparticles, which were kept in dispersion (did not precipitate out), showing that size is important in obtaining good yields in C–C Heck catalysis (where cocktail-type catalysis could explain the conversion). Nanoparticles of this size also act as a reservoir of soluble palladium species that behave as the true catalyst. The second best conversion was observed in N,N-dimethylformamide with sodium citrate, where citrate may have added extra protection, and since the palladium(0) nanoparticles were small, cocktail-type catalysis was not involved in obtaining high yields. Graphic Abstract Palladium nanoparticles (dpeaa)DE-He213 Nanoparticle size (dpeaa)DE-He213 Heck C–C cross-coupling reactions (dpeaa)DE-He213 Palladium reduction (dpeaa)DE-He213 González-García, Tania (orcid)0000-0003-2221-0319 aut Espinoza-Flores, Lorena aut Reyes-Mosso, Alfonsina (orcid)0000-0003-4473-0198 aut Martin, Erika aut Ugalde-Saldivar, V. M. (orcid)0000-0002-9625-8713 aut Enthalten in Catalysis letters Dordrecht [u.a.] : Springer Science + Business Media B.V, 1988 152(2021), 1 vom: 07. Apr., Seite 151-161 (DE-627)306717638 (DE-600)1501518-X 1572-879X nnns volume:152 year:2021 number:1 day:07 month:04 pages:151-161 https://dx.doi.org/10.1007/s10562-021-03613-9 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 152 2021 1 07 04 151-161 |
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10.1007/s10562-021-03613-9 doi (DE-627)SPR045935092 (SPR)s10562-021-03613-9-e DE-627 ger DE-627 rakwb eng Redón, Rocío verfasserin (orcid)0000-0001-8691-8020 aut Palladium Nanoparticles from Different Reducing Systems as Heck Catalysts 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2021 Palladium(0) nanoparticles have been widely used in cross coupling reactions, including Heck reactions. For this study, we synthesized palladium(0) nanoparticles in colloidal suspension using different combinations of solvents and reducing methods under aerobic conditions. The variation in systems used to synthesize palladium(0) nanoparticles resulted in different nanoparticle sizes. To investigate whether the particle size had an effect on catalysis, we first used common Heck C–C cross-coupling reaction conditions (200 °C and 18 h). In addition, we omitted the use of stabilizing agents, other than the solvent and/or the anions in the initial nanoparticle synthesis, since the use of stabilizing agents adds cost and processing time to catalysis. All of the catalysts investigated worked in the cross coupling C–C Heck reaction, but yields did not show appreciable differences, as high temperature and long reaction times promote a high reduction of palladium(II). Therefore, we decided to work with a temperature and reaction time in which conversion would start to be observed (minimum reaction conditions). The experiments to determine minimum reaction conditions showed that this would be 120 °C and 10 h, therefore we used these conditions in Heck C–C cross-coupling reactions and all the palladium nanoparticle systems. The best C–C catalysis conversion was observed when N,N-dimethylformamide was used as solvent in the absence of reducing agent. This catalyst system resulted in the largest possible nanoparticles, which were kept in dispersion (did not precipitate out), showing that size is important in obtaining good yields in C–C Heck catalysis (where cocktail-type catalysis could explain the conversion). Nanoparticles of this size also act as a reservoir of soluble palladium species that behave as the true catalyst. The second best conversion was observed in N,N-dimethylformamide with sodium citrate, where citrate may have added extra protection, and since the palladium(0) nanoparticles were small, cocktail-type catalysis was not involved in obtaining high yields. Graphic Abstract Palladium nanoparticles (dpeaa)DE-He213 Nanoparticle size (dpeaa)DE-He213 Heck C–C cross-coupling reactions (dpeaa)DE-He213 Palladium reduction (dpeaa)DE-He213 González-García, Tania (orcid)0000-0003-2221-0319 aut Espinoza-Flores, Lorena aut Reyes-Mosso, Alfonsina (orcid)0000-0003-4473-0198 aut Martin, Erika aut Ugalde-Saldivar, V. M. (orcid)0000-0002-9625-8713 aut Enthalten in Catalysis letters Dordrecht [u.a.] : Springer Science + Business Media B.V, 1988 152(2021), 1 vom: 07. Apr., Seite 151-161 (DE-627)306717638 (DE-600)1501518-X 1572-879X nnns volume:152 year:2021 number:1 day:07 month:04 pages:151-161 https://dx.doi.org/10.1007/s10562-021-03613-9 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 152 2021 1 07 04 151-161 |
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10.1007/s10562-021-03613-9 doi (DE-627)SPR045935092 (SPR)s10562-021-03613-9-e DE-627 ger DE-627 rakwb eng Redón, Rocío verfasserin (orcid)0000-0001-8691-8020 aut Palladium Nanoparticles from Different Reducing Systems as Heck Catalysts 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2021 Palladium(0) nanoparticles have been widely used in cross coupling reactions, including Heck reactions. For this study, we synthesized palladium(0) nanoparticles in colloidal suspension using different combinations of solvents and reducing methods under aerobic conditions. The variation in systems used to synthesize palladium(0) nanoparticles resulted in different nanoparticle sizes. To investigate whether the particle size had an effect on catalysis, we first used common Heck C–C cross-coupling reaction conditions (200 °C and 18 h). In addition, we omitted the use of stabilizing agents, other than the solvent and/or the anions in the initial nanoparticle synthesis, since the use of stabilizing agents adds cost and processing time to catalysis. All of the catalysts investigated worked in the cross coupling C–C Heck reaction, but yields did not show appreciable differences, as high temperature and long reaction times promote a high reduction of palladium(II). Therefore, we decided to work with a temperature and reaction time in which conversion would start to be observed (minimum reaction conditions). The experiments to determine minimum reaction conditions showed that this would be 120 °C and 10 h, therefore we used these conditions in Heck C–C cross-coupling reactions and all the palladium nanoparticle systems. The best C–C catalysis conversion was observed when N,N-dimethylformamide was used as solvent in the absence of reducing agent. This catalyst system resulted in the largest possible nanoparticles, which were kept in dispersion (did not precipitate out), showing that size is important in obtaining good yields in C–C Heck catalysis (where cocktail-type catalysis could explain the conversion). Nanoparticles of this size also act as a reservoir of soluble palladium species that behave as the true catalyst. The second best conversion was observed in N,N-dimethylformamide with sodium citrate, where citrate may have added extra protection, and since the palladium(0) nanoparticles were small, cocktail-type catalysis was not involved in obtaining high yields. Graphic Abstract Palladium nanoparticles (dpeaa)DE-He213 Nanoparticle size (dpeaa)DE-He213 Heck C–C cross-coupling reactions (dpeaa)DE-He213 Palladium reduction (dpeaa)DE-He213 González-García, Tania (orcid)0000-0003-2221-0319 aut Espinoza-Flores, Lorena aut Reyes-Mosso, Alfonsina (orcid)0000-0003-4473-0198 aut Martin, Erika aut Ugalde-Saldivar, V. M. (orcid)0000-0002-9625-8713 aut Enthalten in Catalysis letters Dordrecht [u.a.] : Springer Science + Business Media B.V, 1988 152(2021), 1 vom: 07. Apr., Seite 151-161 (DE-627)306717638 (DE-600)1501518-X 1572-879X nnns volume:152 year:2021 number:1 day:07 month:04 pages:151-161 https://dx.doi.org/10.1007/s10562-021-03613-9 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 152 2021 1 07 04 151-161 |
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Redón, Rocío @@aut@@ González-García, Tania @@aut@@ Espinoza-Flores, Lorena @@aut@@ Reyes-Mosso, Alfonsina @@aut@@ Martin, Erika @@aut@@ Ugalde-Saldivar, V. M. @@aut@@ |
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For this study, we synthesized palladium(0) nanoparticles in colloidal suspension using different combinations of solvents and reducing methods under aerobic conditions. The variation in systems used to synthesize palladium(0) nanoparticles resulted in different nanoparticle sizes. To investigate whether the particle size had an effect on catalysis, we first used common Heck C–C cross-coupling reaction conditions (200 °C and 18 h). In addition, we omitted the use of stabilizing agents, other than the solvent and/or the anions in the initial nanoparticle synthesis, since the use of stabilizing agents adds cost and processing time to catalysis. All of the catalysts investigated worked in the cross coupling C–C Heck reaction, but yields did not show appreciable differences, as high temperature and long reaction times promote a high reduction of palladium(II). Therefore, we decided to work with a temperature and reaction time in which conversion would start to be observed (minimum reaction conditions). The experiments to determine minimum reaction conditions showed that this would be 120 °C and 10 h, therefore we used these conditions in Heck C–C cross-coupling reactions and all the palladium nanoparticle systems. The best C–C catalysis conversion was observed when N,N-dimethylformamide was used as solvent in the absence of reducing agent. This catalyst system resulted in the largest possible nanoparticles, which were kept in dispersion (did not precipitate out), showing that size is important in obtaining good yields in C–C Heck catalysis (where cocktail-type catalysis could explain the conversion). Nanoparticles of this size also act as a reservoir of soluble palladium species that behave as the true catalyst. The second best conversion was observed in N,N-dimethylformamide with sodium citrate, where citrate may have added extra protection, and since the palladium(0) nanoparticles were small, cocktail-type catalysis was not involved in obtaining high yields. 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Redón, Rocío |
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Redón, Rocío misc Palladium nanoparticles misc Nanoparticle size misc Heck C–C cross-coupling reactions misc Palladium reduction Palladium Nanoparticles from Different Reducing Systems as Heck Catalysts |
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Palladium Nanoparticles from Different Reducing Systems as Heck Catalysts Palladium nanoparticles (dpeaa)DE-He213 Nanoparticle size (dpeaa)DE-He213 Heck C–C cross-coupling reactions (dpeaa)DE-He213 Palladium reduction (dpeaa)DE-He213 |
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palladium nanoparticles from different reducing systems as heck catalysts |
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Palladium Nanoparticles from Different Reducing Systems as Heck Catalysts |
| abstract |
Palladium(0) nanoparticles have been widely used in cross coupling reactions, including Heck reactions. For this study, we synthesized palladium(0) nanoparticles in colloidal suspension using different combinations of solvents and reducing methods under aerobic conditions. The variation in systems used to synthesize palladium(0) nanoparticles resulted in different nanoparticle sizes. To investigate whether the particle size had an effect on catalysis, we first used common Heck C–C cross-coupling reaction conditions (200 °C and 18 h). In addition, we omitted the use of stabilizing agents, other than the solvent and/or the anions in the initial nanoparticle synthesis, since the use of stabilizing agents adds cost and processing time to catalysis. All of the catalysts investigated worked in the cross coupling C–C Heck reaction, but yields did not show appreciable differences, as high temperature and long reaction times promote a high reduction of palladium(II). Therefore, we decided to work with a temperature and reaction time in which conversion would start to be observed (minimum reaction conditions). The experiments to determine minimum reaction conditions showed that this would be 120 °C and 10 h, therefore we used these conditions in Heck C–C cross-coupling reactions and all the palladium nanoparticle systems. The best C–C catalysis conversion was observed when N,N-dimethylformamide was used as solvent in the absence of reducing agent. This catalyst system resulted in the largest possible nanoparticles, which were kept in dispersion (did not precipitate out), showing that size is important in obtaining good yields in C–C Heck catalysis (where cocktail-type catalysis could explain the conversion). Nanoparticles of this size also act as a reservoir of soluble palladium species that behave as the true catalyst. The second best conversion was observed in N,N-dimethylformamide with sodium citrate, where citrate may have added extra protection, and since the palladium(0) nanoparticles were small, cocktail-type catalysis was not involved in obtaining high yields. Graphic Abstract © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2021 |
| abstractGer |
Palladium(0) nanoparticles have been widely used in cross coupling reactions, including Heck reactions. For this study, we synthesized palladium(0) nanoparticles in colloidal suspension using different combinations of solvents and reducing methods under aerobic conditions. The variation in systems used to synthesize palladium(0) nanoparticles resulted in different nanoparticle sizes. To investigate whether the particle size had an effect on catalysis, we first used common Heck C–C cross-coupling reaction conditions (200 °C and 18 h). In addition, we omitted the use of stabilizing agents, other than the solvent and/or the anions in the initial nanoparticle synthesis, since the use of stabilizing agents adds cost and processing time to catalysis. All of the catalysts investigated worked in the cross coupling C–C Heck reaction, but yields did not show appreciable differences, as high temperature and long reaction times promote a high reduction of palladium(II). Therefore, we decided to work with a temperature and reaction time in which conversion would start to be observed (minimum reaction conditions). The experiments to determine minimum reaction conditions showed that this would be 120 °C and 10 h, therefore we used these conditions in Heck C–C cross-coupling reactions and all the palladium nanoparticle systems. The best C–C catalysis conversion was observed when N,N-dimethylformamide was used as solvent in the absence of reducing agent. This catalyst system resulted in the largest possible nanoparticles, which were kept in dispersion (did not precipitate out), showing that size is important in obtaining good yields in C–C Heck catalysis (where cocktail-type catalysis could explain the conversion). Nanoparticles of this size also act as a reservoir of soluble palladium species that behave as the true catalyst. The second best conversion was observed in N,N-dimethylformamide with sodium citrate, where citrate may have added extra protection, and since the palladium(0) nanoparticles were small, cocktail-type catalysis was not involved in obtaining high yields. Graphic Abstract © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2021 |
| abstract_unstemmed |
Palladium(0) nanoparticles have been widely used in cross coupling reactions, including Heck reactions. For this study, we synthesized palladium(0) nanoparticles in colloidal suspension using different combinations of solvents and reducing methods under aerobic conditions. The variation in systems used to synthesize palladium(0) nanoparticles resulted in different nanoparticle sizes. To investigate whether the particle size had an effect on catalysis, we first used common Heck C–C cross-coupling reaction conditions (200 °C and 18 h). In addition, we omitted the use of stabilizing agents, other than the solvent and/or the anions in the initial nanoparticle synthesis, since the use of stabilizing agents adds cost and processing time to catalysis. All of the catalysts investigated worked in the cross coupling C–C Heck reaction, but yields did not show appreciable differences, as high temperature and long reaction times promote a high reduction of palladium(II). Therefore, we decided to work with a temperature and reaction time in which conversion would start to be observed (minimum reaction conditions). The experiments to determine minimum reaction conditions showed that this would be 120 °C and 10 h, therefore we used these conditions in Heck C–C cross-coupling reactions and all the palladium nanoparticle systems. The best C–C catalysis conversion was observed when N,N-dimethylformamide was used as solvent in the absence of reducing agent. This catalyst system resulted in the largest possible nanoparticles, which were kept in dispersion (did not precipitate out), showing that size is important in obtaining good yields in C–C Heck catalysis (where cocktail-type catalysis could explain the conversion). Nanoparticles of this size also act as a reservoir of soluble palladium species that behave as the true catalyst. The second best conversion was observed in N,N-dimethylformamide with sodium citrate, where citrate may have added extra protection, and since the palladium(0) nanoparticles were small, cocktail-type catalysis was not involved in obtaining high yields. Graphic Abstract © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2021 |
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| title_short |
Palladium Nanoparticles from Different Reducing Systems as Heck Catalysts |
| url |
https://dx.doi.org/10.1007/s10562-021-03613-9 |
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| author2 |
González-García, Tania Espinoza-Flores, Lorena Reyes-Mosso, Alfonsina Martin, Erika Ugalde-Saldivar, V. M. |
| author2Str |
González-García, Tania Espinoza-Flores, Lorena Reyes-Mosso, Alfonsina Martin, Erika Ugalde-Saldivar, V. M. |
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10.1007/s10562-021-03613-9 |
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2024-07-03T19:15:24.946Z |
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| score |
7.3992968 |