Working together to avoid unwanted reactions: Hydroformylation/O-acylation of terpene-based hydroxyolefins
The application of hydroformylation to substrates containing hydroxyl groups tends to be problematic because the formed aldehydes can react with the hydroxyl moiety in undesired ways. Herein we describe a protocol in which the hydroxyl group is O-acylated concomitantly with hydroformylation in a one...
Ausführliche Beschreibung
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| Autor*in: |
Delolo, Fábio G. [verfasserIn] Vieira, Gabriel M. [verfasserIn] Avendaño-Villarreal, Jesus A. [verfasserIn] de Oliveira Dias, Adelson [verfasserIn] dos Santos, Eduardo N. [verfasserIn] Gusevskaya, Elena V. [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2023 |
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| Schlagwörter: |
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| Übergeordnetes Werk: |
Enthalten in: Journal of catalysis - Amsterdam [u.a.] : Elsevier, 1962, 421, Seite 20-29 |
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| Übergeordnetes Werk: |
volume:421 ; pages:20-29 |
| DOI / URN: |
10.1016/j.jcat.2023.03.003 |
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| 520 | |a The application of hydroformylation to substrates containing hydroxyl groups tends to be problematic because the formed aldehydes can react with the hydroxyl moiety in undesired ways. Herein we describe a protocol in which the hydroxyl group is O-acylated concomitantly with hydroformylation in a one-pot catalytic process, preventing undesired side reactions. This strategy is applied for the renewable terpenes perillyl alcohol, carveol, myrtenol, and isopulegol, as well as for isoprenol and the biomass-based nopol. The selectivity for the acetoxyaldehydes is much higher than for the analogous hydroxyaldehydes produced by hydroformylation only. Furthermore, the new products obtained through a synthetically efficient process directly from renewable resources are promising candidates to new fragrance components as they contain aldehyde and acetoxy ester functionalities, both known to aggregate olfactory properties to molecules. | ||
| 650 | 4 | |a Terpenes | |
| 650 | 4 | |a Renewables | |
| 650 | 4 | |a Fragrance | |
| 650 | 4 | |a Flavor | |
| 650 | 4 | |a Tandem catalysis | |
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| 700 | 1 | |a Vieira, Gabriel M. |e verfasserin |4 aut | |
| 700 | 1 | |a Avendaño-Villarreal, Jesus A. |e verfasserin |0 (orcid)0000-0001-6810-543X |4 aut | |
| 700 | 1 | |a de Oliveira Dias, Adelson |e verfasserin |4 aut | |
| 700 | 1 | |a dos Santos, Eduardo N. |e verfasserin |4 aut | |
| 700 | 1 | |a Gusevskaya, Elena V. |e verfasserin |0 (orcid)0000-0002-4894-8402 |4 aut | |
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10.1016/j.jcat.2023.03.003 doi (DE-627)ELV06281091X (ELSEVIER)S0021-9517(23)00083-0 DE-627 ger DE-627 rda eng 540 VZ 35.00 bkl Delolo, Fábio G. verfasserin (orcid)0000-0001-7968-9506 aut Working together to avoid unwanted reactions: Hydroformylation/O-acylation of terpene-based hydroxyolefins 2023 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The application of hydroformylation to substrates containing hydroxyl groups tends to be problematic because the formed aldehydes can react with the hydroxyl moiety in undesired ways. Herein we describe a protocol in which the hydroxyl group is O-acylated concomitantly with hydroformylation in a one-pot catalytic process, preventing undesired side reactions. This strategy is applied for the renewable terpenes perillyl alcohol, carveol, myrtenol, and isopulegol, as well as for isoprenol and the biomass-based nopol. The selectivity for the acetoxyaldehydes is much higher than for the analogous hydroxyaldehydes produced by hydroformylation only. Furthermore, the new products obtained through a synthetically efficient process directly from renewable resources are promising candidates to new fragrance components as they contain aldehyde and acetoxy ester functionalities, both known to aggregate olfactory properties to molecules. Terpenes Renewables Fragrance Flavor Tandem catalysis Green solvent Vieira, Gabriel M. verfasserin aut Avendaño-Villarreal, Jesus A. verfasserin (orcid)0000-0001-6810-543X aut de Oliveira Dias, Adelson verfasserin aut dos Santos, Eduardo N. verfasserin aut Gusevskaya, Elena V. verfasserin (orcid)0000-0002-4894-8402 aut Enthalten in Journal of catalysis Amsterdam [u.a.] : Elsevier, 1962 421, Seite 20-29 Online-Ressource (DE-627)266890865 (DE-600)1468993-5 (DE-576)103373144 1090-2694 nnns volume:421 pages:20-29 GBV_USEFLAG_U GBV_ELV SYSFLAG_U GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 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_150 GBV_ILN_151 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 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_2034 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2088 GBV_ILN_2106 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4242 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_4333 GBV_ILN_4334 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 35.00 Chemie: Allgemeines VZ AR 421 20-29 |
| spelling |
10.1016/j.jcat.2023.03.003 doi (DE-627)ELV06281091X (ELSEVIER)S0021-9517(23)00083-0 DE-627 ger DE-627 rda eng 540 VZ 35.00 bkl Delolo, Fábio G. verfasserin (orcid)0000-0001-7968-9506 aut Working together to avoid unwanted reactions: Hydroformylation/O-acylation of terpene-based hydroxyolefins 2023 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The application of hydroformylation to substrates containing hydroxyl groups tends to be problematic because the formed aldehydes can react with the hydroxyl moiety in undesired ways. Herein we describe a protocol in which the hydroxyl group is O-acylated concomitantly with hydroformylation in a one-pot catalytic process, preventing undesired side reactions. This strategy is applied for the renewable terpenes perillyl alcohol, carveol, myrtenol, and isopulegol, as well as for isoprenol and the biomass-based nopol. The selectivity for the acetoxyaldehydes is much higher than for the analogous hydroxyaldehydes produced by hydroformylation only. Furthermore, the new products obtained through a synthetically efficient process directly from renewable resources are promising candidates to new fragrance components as they contain aldehyde and acetoxy ester functionalities, both known to aggregate olfactory properties to molecules. Terpenes Renewables Fragrance Flavor Tandem catalysis Green solvent Vieira, Gabriel M. verfasserin aut Avendaño-Villarreal, Jesus A. verfasserin (orcid)0000-0001-6810-543X aut de Oliveira Dias, Adelson verfasserin aut dos Santos, Eduardo N. verfasserin aut Gusevskaya, Elena V. verfasserin (orcid)0000-0002-4894-8402 aut Enthalten in Journal of catalysis Amsterdam [u.a.] : Elsevier, 1962 421, Seite 20-29 Online-Ressource (DE-627)266890865 (DE-600)1468993-5 (DE-576)103373144 1090-2694 nnns volume:421 pages:20-29 GBV_USEFLAG_U GBV_ELV SYSFLAG_U GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 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_150 GBV_ILN_151 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 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_2034 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2088 GBV_ILN_2106 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4242 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_4333 GBV_ILN_4334 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 35.00 Chemie: Allgemeines VZ AR 421 20-29 |
| allfields_unstemmed |
10.1016/j.jcat.2023.03.003 doi (DE-627)ELV06281091X (ELSEVIER)S0021-9517(23)00083-0 DE-627 ger DE-627 rda eng 540 VZ 35.00 bkl Delolo, Fábio G. verfasserin (orcid)0000-0001-7968-9506 aut Working together to avoid unwanted reactions: Hydroformylation/O-acylation of terpene-based hydroxyolefins 2023 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The application of hydroformylation to substrates containing hydroxyl groups tends to be problematic because the formed aldehydes can react with the hydroxyl moiety in undesired ways. Herein we describe a protocol in which the hydroxyl group is O-acylated concomitantly with hydroformylation in a one-pot catalytic process, preventing undesired side reactions. This strategy is applied for the renewable terpenes perillyl alcohol, carveol, myrtenol, and isopulegol, as well as for isoprenol and the biomass-based nopol. The selectivity for the acetoxyaldehydes is much higher than for the analogous hydroxyaldehydes produced by hydroformylation only. Furthermore, the new products obtained through a synthetically efficient process directly from renewable resources are promising candidates to new fragrance components as they contain aldehyde and acetoxy ester functionalities, both known to aggregate olfactory properties to molecules. Terpenes Renewables Fragrance Flavor Tandem catalysis Green solvent Vieira, Gabriel M. verfasserin aut Avendaño-Villarreal, Jesus A. verfasserin (orcid)0000-0001-6810-543X aut de Oliveira Dias, Adelson verfasserin aut dos Santos, Eduardo N. verfasserin aut Gusevskaya, Elena V. verfasserin (orcid)0000-0002-4894-8402 aut Enthalten in Journal of catalysis Amsterdam [u.a.] : Elsevier, 1962 421, Seite 20-29 Online-Ressource (DE-627)266890865 (DE-600)1468993-5 (DE-576)103373144 1090-2694 nnns volume:421 pages:20-29 GBV_USEFLAG_U GBV_ELV SYSFLAG_U GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 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_150 GBV_ILN_151 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 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_2034 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2088 GBV_ILN_2106 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4242 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_4333 GBV_ILN_4334 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 35.00 Chemie: Allgemeines VZ AR 421 20-29 |
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10.1016/j.jcat.2023.03.003 doi (DE-627)ELV06281091X (ELSEVIER)S0021-9517(23)00083-0 DE-627 ger DE-627 rda eng 540 VZ 35.00 bkl Delolo, Fábio G. verfasserin (orcid)0000-0001-7968-9506 aut Working together to avoid unwanted reactions: Hydroformylation/O-acylation of terpene-based hydroxyolefins 2023 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The application of hydroformylation to substrates containing hydroxyl groups tends to be problematic because the formed aldehydes can react with the hydroxyl moiety in undesired ways. Herein we describe a protocol in which the hydroxyl group is O-acylated concomitantly with hydroformylation in a one-pot catalytic process, preventing undesired side reactions. This strategy is applied for the renewable terpenes perillyl alcohol, carveol, myrtenol, and isopulegol, as well as for isoprenol and the biomass-based nopol. The selectivity for the acetoxyaldehydes is much higher than for the analogous hydroxyaldehydes produced by hydroformylation only. Furthermore, the new products obtained through a synthetically efficient process directly from renewable resources are promising candidates to new fragrance components as they contain aldehyde and acetoxy ester functionalities, both known to aggregate olfactory properties to molecules. Terpenes Renewables Fragrance Flavor Tandem catalysis Green solvent Vieira, Gabriel M. verfasserin aut Avendaño-Villarreal, Jesus A. verfasserin (orcid)0000-0001-6810-543X aut de Oliveira Dias, Adelson verfasserin aut dos Santos, Eduardo N. verfasserin aut Gusevskaya, Elena V. verfasserin (orcid)0000-0002-4894-8402 aut Enthalten in Journal of catalysis Amsterdam [u.a.] : Elsevier, 1962 421, Seite 20-29 Online-Ressource (DE-627)266890865 (DE-600)1468993-5 (DE-576)103373144 1090-2694 nnns volume:421 pages:20-29 GBV_USEFLAG_U GBV_ELV SYSFLAG_U GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 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_150 GBV_ILN_151 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 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_2034 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2088 GBV_ILN_2106 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4242 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_4333 GBV_ILN_4334 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 35.00 Chemie: Allgemeines VZ AR 421 20-29 |
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10.1016/j.jcat.2023.03.003 doi (DE-627)ELV06281091X (ELSEVIER)S0021-9517(23)00083-0 DE-627 ger DE-627 rda eng 540 VZ 35.00 bkl Delolo, Fábio G. verfasserin (orcid)0000-0001-7968-9506 aut Working together to avoid unwanted reactions: Hydroformylation/O-acylation of terpene-based hydroxyolefins 2023 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The application of hydroformylation to substrates containing hydroxyl groups tends to be problematic because the formed aldehydes can react with the hydroxyl moiety in undesired ways. Herein we describe a protocol in which the hydroxyl group is O-acylated concomitantly with hydroformylation in a one-pot catalytic process, preventing undesired side reactions. This strategy is applied for the renewable terpenes perillyl alcohol, carveol, myrtenol, and isopulegol, as well as for isoprenol and the biomass-based nopol. The selectivity for the acetoxyaldehydes is much higher than for the analogous hydroxyaldehydes produced by hydroformylation only. Furthermore, the new products obtained through a synthetically efficient process directly from renewable resources are promising candidates to new fragrance components as they contain aldehyde and acetoxy ester functionalities, both known to aggregate olfactory properties to molecules. Terpenes Renewables Fragrance Flavor Tandem catalysis Green solvent Vieira, Gabriel M. verfasserin aut Avendaño-Villarreal, Jesus A. verfasserin (orcid)0000-0001-6810-543X aut de Oliveira Dias, Adelson verfasserin aut dos Santos, Eduardo N. verfasserin aut Gusevskaya, Elena V. verfasserin (orcid)0000-0002-4894-8402 aut Enthalten in Journal of catalysis Amsterdam [u.a.] : Elsevier, 1962 421, Seite 20-29 Online-Ressource (DE-627)266890865 (DE-600)1468993-5 (DE-576)103373144 1090-2694 nnns volume:421 pages:20-29 GBV_USEFLAG_U GBV_ELV SYSFLAG_U GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 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_150 GBV_ILN_151 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 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_2034 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2088 GBV_ILN_2106 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4242 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_4333 GBV_ILN_4334 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 35.00 Chemie: Allgemeines VZ AR 421 20-29 |
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Delolo, Fábio G. |
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Delolo, Fábio G. ddc 540 bkl 35.00 misc Terpenes misc Renewables misc Fragrance misc Flavor misc Tandem catalysis misc Green solvent Working together to avoid unwanted reactions: Hydroformylation/O-acylation of terpene-based hydroxyolefins |
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540 VZ 35.00 bkl Working together to avoid unwanted reactions: Hydroformylation/O-acylation of terpene-based hydroxyolefins Terpenes Renewables Fragrance Flavor Tandem catalysis Green solvent |
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working together to avoid unwanted reactions: hydroformylation/o-acylation of terpene-based hydroxyolefins |
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Working together to avoid unwanted reactions: Hydroformylation/O-acylation of terpene-based hydroxyolefins |
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The application of hydroformylation to substrates containing hydroxyl groups tends to be problematic because the formed aldehydes can react with the hydroxyl moiety in undesired ways. Herein we describe a protocol in which the hydroxyl group is O-acylated concomitantly with hydroformylation in a one-pot catalytic process, preventing undesired side reactions. This strategy is applied for the renewable terpenes perillyl alcohol, carveol, myrtenol, and isopulegol, as well as for isoprenol and the biomass-based nopol. The selectivity for the acetoxyaldehydes is much higher than for the analogous hydroxyaldehydes produced by hydroformylation only. Furthermore, the new products obtained through a synthetically efficient process directly from renewable resources are promising candidates to new fragrance components as they contain aldehyde and acetoxy ester functionalities, both known to aggregate olfactory properties to molecules. |
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The application of hydroformylation to substrates containing hydroxyl groups tends to be problematic because the formed aldehydes can react with the hydroxyl moiety in undesired ways. Herein we describe a protocol in which the hydroxyl group is O-acylated concomitantly with hydroformylation in a one-pot catalytic process, preventing undesired side reactions. This strategy is applied for the renewable terpenes perillyl alcohol, carveol, myrtenol, and isopulegol, as well as for isoprenol and the biomass-based nopol. The selectivity for the acetoxyaldehydes is much higher than for the analogous hydroxyaldehydes produced by hydroformylation only. Furthermore, the new products obtained through a synthetically efficient process directly from renewable resources are promising candidates to new fragrance components as they contain aldehyde and acetoxy ester functionalities, both known to aggregate olfactory properties to molecules. |
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The application of hydroformylation to substrates containing hydroxyl groups tends to be problematic because the formed aldehydes can react with the hydroxyl moiety in undesired ways. Herein we describe a protocol in which the hydroxyl group is O-acylated concomitantly with hydroformylation in a one-pot catalytic process, preventing undesired side reactions. This strategy is applied for the renewable terpenes perillyl alcohol, carveol, myrtenol, and isopulegol, as well as for isoprenol and the biomass-based nopol. The selectivity for the acetoxyaldehydes is much higher than for the analogous hydroxyaldehydes produced by hydroformylation only. Furthermore, the new products obtained through a synthetically efficient process directly from renewable resources are promising candidates to new fragrance components as they contain aldehyde and acetoxy ester functionalities, both known to aggregate olfactory properties to molecules. |
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Working together to avoid unwanted reactions: Hydroformylation/O-acylation of terpene-based hydroxyolefins |
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| score |
7.398241 |