Maryam Tukhani, Abdolreza Hajipour and Alireza Najafi Chermahini
{"title":"磁性介孔磷酸锆(MMZP-Pr-SO3H):可持续制备苯基四唑和 2-取代苯并唑的高效可重复使用催化剂","authors":"Maryam Tukhani, Abdolreza Hajipour and Alireza Najafi Chermahini","doi":"10.1039/D4RE00248B","DOIUrl":null,"url":null,"abstract":"<p >Based on the synthesis of mesoporous zirconium phosphate in the presence of magnetic nanoparticles (NPs) and its functionalization with propyl sulfonic acid groups, a new and effective heterogeneous acidic catalyst (MMZP-Pr-SO<small><sub>3</sub></small>H) was prepared. It was attempted to alter the catalyst's properties in this study in order to boost reactant conversion yield and remove unselective reaction pathways by offering complementary characterization. MMZP-Pr-SO<small><sub>3</sub></small>H was used for the eco-friendly and efficient preparation of various tetrazole derivatives through condensation of aryl nitriles and sodium azide in water solvent at 60 °C. This protocol was also practical for benzoazole (benzimidazole, benzoxazole, and benzothiazole) synthesis starting from the <em>in situ</em> oxidation of benzyl alcohol, which demonstrates the dual role of the MMZP-Pr-SO<small><sub>3</sub></small>H catalyst in oxidation and condensation reactions. For both investigated reactions quantitative conversion of the desired product was obtained and the catalyst was simply separated from the reaction mixture by employing an external magnetic field. The MMZP-Pr-SO<small><sub>3</sub></small>H catalyst was regenerated and reused for at least 6 runs without a significant decrease in reaction yield. With the aid of lenses on catalyst active sites, the structural characteristics of the recycled catalyst were thoroughly examined. In contrast to our earlier attempts to study the structural features of the MZP and ZP substrates and use them as catalysts for organic reactions, the MMZP-Pr-SO<small><sub>3</sub></small>H catalyst offers a sustainable and clean synthetic methodology for the large-scale preparation of derivatives of tetrazoles and benzoazoles.</p>","PeriodicalId":101,"journal":{"name":"Reaction Chemistry & Engineering","volume":" 12","pages":" 3191-3210"},"PeriodicalIF":3.4000,"publicationDate":"2024-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Magnetic mesoporous zirconium phosphate (MMZP-Pr-SO3H): a highly efficient and reusable catalyst for sustainable preparation of phenyl tetrazole and 2-substituted benzoazoles†\",\"authors\":\"Maryam Tukhani, Abdolreza Hajipour and Alireza Najafi Chermahini\",\"doi\":\"10.1039/D4RE00248B\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Based on the synthesis of mesoporous zirconium phosphate in the presence of magnetic nanoparticles (NPs) and its functionalization with propyl sulfonic acid groups, a new and effective heterogeneous acidic catalyst (MMZP-Pr-SO<small><sub>3</sub></small>H) was prepared. It was attempted to alter the catalyst's properties in this study in order to boost reactant conversion yield and remove unselective reaction pathways by offering complementary characterization. MMZP-Pr-SO<small><sub>3</sub></small>H was used for the eco-friendly and efficient preparation of various tetrazole derivatives through condensation of aryl nitriles and sodium azide in water solvent at 60 °C. This protocol was also practical for benzoazole (benzimidazole, benzoxazole, and benzothiazole) synthesis starting from the <em>in situ</em> oxidation of benzyl alcohol, which demonstrates the dual role of the MMZP-Pr-SO<small><sub>3</sub></small>H catalyst in oxidation and condensation reactions. For both investigated reactions quantitative conversion of the desired product was obtained and the catalyst was simply separated from the reaction mixture by employing an external magnetic field. The MMZP-Pr-SO<small><sub>3</sub></small>H catalyst was regenerated and reused for at least 6 runs without a significant decrease in reaction yield. With the aid of lenses on catalyst active sites, the structural characteristics of the recycled catalyst were thoroughly examined. In contrast to our earlier attempts to study the structural features of the MZP and ZP substrates and use them as catalysts for organic reactions, the MMZP-Pr-SO<small><sub>3</sub></small>H catalyst offers a sustainable and clean synthetic methodology for the large-scale preparation of derivatives of tetrazoles and benzoazoles.</p>\",\"PeriodicalId\":101,\"journal\":{\"name\":\"Reaction Chemistry & Engineering\",\"volume\":\" 12\",\"pages\":\" 3191-3210\"},\"PeriodicalIF\":3.4000,\"publicationDate\":\"2024-09-03\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Reaction Chemistry & Engineering\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.rsc.org/en/content/articlelanding/2024/re/d4re00248b\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Reaction Chemistry & Engineering","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/re/d4re00248b","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Magnetic mesoporous zirconium phosphate (MMZP-Pr-SO3H): a highly efficient and reusable catalyst for sustainable preparation of phenyl tetrazole and 2-substituted benzoazoles†
Based on the synthesis of mesoporous zirconium phosphate in the presence of magnetic nanoparticles (NPs) and its functionalization with propyl sulfonic acid groups, a new and effective heterogeneous acidic catalyst (MMZP-Pr-SO3H) was prepared. It was attempted to alter the catalyst's properties in this study in order to boost reactant conversion yield and remove unselective reaction pathways by offering complementary characterization. MMZP-Pr-SO3H was used for the eco-friendly and efficient preparation of various tetrazole derivatives through condensation of aryl nitriles and sodium azide in water solvent at 60 °C. This protocol was also practical for benzoazole (benzimidazole, benzoxazole, and benzothiazole) synthesis starting from the in situ oxidation of benzyl alcohol, which demonstrates the dual role of the MMZP-Pr-SO3H catalyst in oxidation and condensation reactions. For both investigated reactions quantitative conversion of the desired product was obtained and the catalyst was simply separated from the reaction mixture by employing an external magnetic field. The MMZP-Pr-SO3H catalyst was regenerated and reused for at least 6 runs without a significant decrease in reaction yield. With the aid of lenses on catalyst active sites, the structural characteristics of the recycled catalyst were thoroughly examined. In contrast to our earlier attempts to study the structural features of the MZP and ZP substrates and use them as catalysts for organic reactions, the MMZP-Pr-SO3H catalyst offers a sustainable and clean synthetic methodology for the large-scale preparation of derivatives of tetrazoles and benzoazoles.
期刊介绍:
Reaction Chemistry & Engineering is a new journal reporting cutting edge research into all aspects of making molecules for the benefit of fundamental research, applied processes and wider society.
From fundamental, molecular-level chemistry to large scale chemical production, Reaction Chemistry & Engineering brings together communities of chemists and chemical engineers working to ensure the crucial role of reaction chemistry in today’s world.