Fatemeh Ghahramani, Yagoub Mansoori, Abolfazl Bezaatpour, Dolores Esquivel, M. Angeles Navarro
{"title":"磁化SBA-15负载双(肟)钯环作为Mizoroki-Heck反应的高效可回收催化剂","authors":"Fatemeh Ghahramani, Yagoub Mansoori, Abolfazl Bezaatpour, Dolores Esquivel, M. Angeles Navarro","doi":"10.1007/s10563-023-09396-w","DOIUrl":null,"url":null,"abstract":"<div><p>Herein, we report the anchoring of a bis(oxime palladacycle) adduct on magnetic mesoporous silica (Fe<sub>3</sub>O<sub>4</sub>@SBA-15). Magnetic mesoporous silica was successively treated with (3-aminopropyl) triethoxysilane (APTES), cyanuric chloride (CC), and 4-hydroxyacetophenone oxime-derived palladacycle to give Fe<sub>3</sub>O<sub>4</sub>@SBA-AP-CC-bis(oxime palladacycle). The obtained nano-catalyst was characterized by FT-IR spectroscopy, CP MAS <sup>13</sup>C NMR spectroscopy, scanning electron microscopy (SEM), vibrating sample magnetometry (VSM), Brunauer–Emmett–Teller surface area measurement (S<sub>BET</sub>) and X-ray diffraction spectroscopy (XRD). X‐Ray photoelectron spectroscopy (XPS) corroborated the (+ 2) oxidation number for palladium. The catalytic potential of Fe<sub>3</sub>O<sub>4</sub>@SBA-AP-CC-bis(oxime palladacycle) was explored in the Mizoroki–Heck reaction. The effects of different reaction conditions, including the solvent, the base, temperature, and palladium content, were studied in detail. The N-methylpyrrolidone (NMP) solvent, 0.5 mol% of the Pd-catalyst, the NaOAc base, and the reaction temperature of 120 °C, provided the best conditions for the Heck cross-coupling reaction. The catalyst showed a wide substrate scope, including aryl halides (I, Br, Cl) and olefins, in the Mizoroki–Heck reaction, using low catalyst loadings viz., Pd 0.09 mol%. The bis(oxime palladacycle) enjoys easy magnetic separation, stability, and recyclability over five runs.</p></div>","PeriodicalId":509,"journal":{"name":"Catalysis Surveys from Asia","volume":"27 3","pages":"232 - 245"},"PeriodicalIF":2.1000,"publicationDate":"2023-04-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s10563-023-09396-w.pdf","citationCount":"0","resultStr":"{\"title\":\"Bis(Oxime Palladacycle) Supported on Magnetized SBA-15 as an Efficient and Retriveble Catalyst for the Mizoroki–Heck Reaction\",\"authors\":\"Fatemeh Ghahramani, Yagoub Mansoori, Abolfazl Bezaatpour, Dolores Esquivel, M. Angeles Navarro\",\"doi\":\"10.1007/s10563-023-09396-w\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Herein, we report the anchoring of a bis(oxime palladacycle) adduct on magnetic mesoporous silica (Fe<sub>3</sub>O<sub>4</sub>@SBA-15). Magnetic mesoporous silica was successively treated with (3-aminopropyl) triethoxysilane (APTES), cyanuric chloride (CC), and 4-hydroxyacetophenone oxime-derived palladacycle to give Fe<sub>3</sub>O<sub>4</sub>@SBA-AP-CC-bis(oxime palladacycle). The obtained nano-catalyst was characterized by FT-IR spectroscopy, CP MAS <sup>13</sup>C NMR spectroscopy, scanning electron microscopy (SEM), vibrating sample magnetometry (VSM), Brunauer–Emmett–Teller surface area measurement (S<sub>BET</sub>) and X-ray diffraction spectroscopy (XRD). X‐Ray photoelectron spectroscopy (XPS) corroborated the (+ 2) oxidation number for palladium. The catalytic potential of Fe<sub>3</sub>O<sub>4</sub>@SBA-AP-CC-bis(oxime palladacycle) was explored in the Mizoroki–Heck reaction. The effects of different reaction conditions, including the solvent, the base, temperature, and palladium content, were studied in detail. The N-methylpyrrolidone (NMP) solvent, 0.5 mol% of the Pd-catalyst, the NaOAc base, and the reaction temperature of 120 °C, provided the best conditions for the Heck cross-coupling reaction. The catalyst showed a wide substrate scope, including aryl halides (I, Br, Cl) and olefins, in the Mizoroki–Heck reaction, using low catalyst loadings viz., Pd 0.09 mol%. 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Bis(Oxime Palladacycle) Supported on Magnetized SBA-15 as an Efficient and Retriveble Catalyst for the Mizoroki–Heck Reaction
Herein, we report the anchoring of a bis(oxime palladacycle) adduct on magnetic mesoporous silica (Fe3O4@SBA-15). Magnetic mesoporous silica was successively treated with (3-aminopropyl) triethoxysilane (APTES), cyanuric chloride (CC), and 4-hydroxyacetophenone oxime-derived palladacycle to give Fe3O4@SBA-AP-CC-bis(oxime palladacycle). The obtained nano-catalyst was characterized by FT-IR spectroscopy, CP MAS 13C NMR spectroscopy, scanning electron microscopy (SEM), vibrating sample magnetometry (VSM), Brunauer–Emmett–Teller surface area measurement (SBET) and X-ray diffraction spectroscopy (XRD). X‐Ray photoelectron spectroscopy (XPS) corroborated the (+ 2) oxidation number for palladium. The catalytic potential of Fe3O4@SBA-AP-CC-bis(oxime palladacycle) was explored in the Mizoroki–Heck reaction. The effects of different reaction conditions, including the solvent, the base, temperature, and palladium content, were studied in detail. The N-methylpyrrolidone (NMP) solvent, 0.5 mol% of the Pd-catalyst, the NaOAc base, and the reaction temperature of 120 °C, provided the best conditions for the Heck cross-coupling reaction. The catalyst showed a wide substrate scope, including aryl halides (I, Br, Cl) and olefins, in the Mizoroki–Heck reaction, using low catalyst loadings viz., Pd 0.09 mol%. The bis(oxime palladacycle) enjoys easy magnetic separation, stability, and recyclability over five runs.
期刊介绍:
Early dissemination of important findings from Asia which may lead to new concepts in catalyst design is the main aim of this journal. Rapid, invited, short reviews and perspectives from academia and industry will constitute the major part of Catalysis Surveys from Asia . Surveys of recent progress and activities in catalytic science and technology and related areas in Asia will be covered regularly as well. We would appreciate critical comments from colleagues throughout the world about articles in Catalysis Surveys from Asia . If requested and thought appropriate, the comments will be included in the journal. We will be very happy if this journal stimulates global communication between scientists and engineers in the world of catalysis.