Giulia Cazzaniga , Gloria Nicastro , Carlo Punta , Alessandro Sacchetti , Stefania Villa , Matteo Mori , Laura Riva
{"title":"负载钯的纤维素基纳米海绵作为高效非均相催化剂用于合成具有药物相关性的具有挑战性的衍生物","authors":"Giulia Cazzaniga , Gloria Nicastro , Carlo Punta , Alessandro Sacchetti , Stefania Villa , Matteo Mori , Laura Riva","doi":"10.1002/ejoc.202500517","DOIUrl":null,"url":null,"abstract":"<div><div>Developing efficient catalytic systems is crucial for synthesizing complex heterocyclic compounds used in pharmaceuticals. However, key motifs, like pyridine and furan derivatives, pose challenges due to regioselectivity and sensitivity to harsh conditions. Conventional homogeneous palladium‐catalyzed cross‐coupling reactions, while effective, suffer from catalyst recovery issues, palladium contamination, and environmental concerns. To overcome these limitations, this study explores cellulose‐based nanosponges as sustainable palladium supports for heterogeneous catalysis, enhancing stability and green chemistry integration. These nanostructured materials, synthesized from cellulose, provide a high‐surface‐area scaffold that enhances uniform palladium dispersion, with a 22% w/w overall loading measured using inductively coupled plasma optical emission spectroscopy, and prevents metal leaching, integrating green chemistry principles and a safe‐and‐sustainable‐by‐design approach. In this work, the optimization of Suzuki–Miyaura couplings using CNS‐Pd under mild conditions, showcasing the efficiency and selectivity of this heterogeneous catalyst in the synthesis of pharmaceutically relevant heterocyclic derivatives, is presented. Notably, high reaction yields (65%–99%) even with unstable boronic derivatives are achieved, which are typically synthesized using homogeneous catalysts, often with poor yields, selectivity and purity of the final products. The obtained results underscore the potential of biopolymer‐based catalysts to drive innovation in sustainable pharmaceutical synthesis, effectively bridging the gap between heterogeneous catalysis and pharmaceutical chemistry.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 36","pages":"Article e202500517"},"PeriodicalIF":2.7000,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Cellulose‐Based Nanosponges Loaded with Palladium as Efficient Heterogeneous Catalysts for the Synthesis of Challenging Derivatives with Pharmaceutical Relevance\",\"authors\":\"Giulia Cazzaniga , Gloria Nicastro , Carlo Punta , Alessandro Sacchetti , Stefania Villa , Matteo Mori , Laura Riva\",\"doi\":\"10.1002/ejoc.202500517\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Developing efficient catalytic systems is crucial for synthesizing complex heterocyclic compounds used in pharmaceuticals. However, key motifs, like pyridine and furan derivatives, pose challenges due to regioselectivity and sensitivity to harsh conditions. Conventional homogeneous palladium‐catalyzed cross‐coupling reactions, while effective, suffer from catalyst recovery issues, palladium contamination, and environmental concerns. To overcome these limitations, this study explores cellulose‐based nanosponges as sustainable palladium supports for heterogeneous catalysis, enhancing stability and green chemistry integration. These nanostructured materials, synthesized from cellulose, provide a high‐surface‐area scaffold that enhances uniform palladium dispersion, with a 22% w/w overall loading measured using inductively coupled plasma optical emission spectroscopy, and prevents metal leaching, integrating green chemistry principles and a safe‐and‐sustainable‐by‐design approach. In this work, the optimization of Suzuki–Miyaura couplings using CNS‐Pd under mild conditions, showcasing the efficiency and selectivity of this heterogeneous catalyst in the synthesis of pharmaceutically relevant heterocyclic derivatives, is presented. Notably, high reaction yields (65%–99%) even with unstable boronic derivatives are achieved, which are typically synthesized using homogeneous catalysts, often with poor yields, selectivity and purity of the final products. The obtained results underscore the potential of biopolymer‐based catalysts to drive innovation in sustainable pharmaceutical synthesis, effectively bridging the gap between heterogeneous catalysis and pharmaceutical chemistry.</div></div>\",\"PeriodicalId\":167,\"journal\":{\"name\":\"European Journal of Organic Chemistry\",\"volume\":\"28 36\",\"pages\":\"Article e202500517\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2025-09-29\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"European Journal of Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1434193X25004591\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1434193X25004591","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Cellulose‐Based Nanosponges Loaded with Palladium as Efficient Heterogeneous Catalysts for the Synthesis of Challenging Derivatives with Pharmaceutical Relevance
Developing efficient catalytic systems is crucial for synthesizing complex heterocyclic compounds used in pharmaceuticals. However, key motifs, like pyridine and furan derivatives, pose challenges due to regioselectivity and sensitivity to harsh conditions. Conventional homogeneous palladium‐catalyzed cross‐coupling reactions, while effective, suffer from catalyst recovery issues, palladium contamination, and environmental concerns. To overcome these limitations, this study explores cellulose‐based nanosponges as sustainable palladium supports for heterogeneous catalysis, enhancing stability and green chemistry integration. These nanostructured materials, synthesized from cellulose, provide a high‐surface‐area scaffold that enhances uniform palladium dispersion, with a 22% w/w overall loading measured using inductively coupled plasma optical emission spectroscopy, and prevents metal leaching, integrating green chemistry principles and a safe‐and‐sustainable‐by‐design approach. In this work, the optimization of Suzuki–Miyaura couplings using CNS‐Pd under mild conditions, showcasing the efficiency and selectivity of this heterogeneous catalyst in the synthesis of pharmaceutically relevant heterocyclic derivatives, is presented. Notably, high reaction yields (65%–99%) even with unstable boronic derivatives are achieved, which are typically synthesized using homogeneous catalysts, often with poor yields, selectivity and purity of the final products. The obtained results underscore the potential of biopolymer‐based catalysts to drive innovation in sustainable pharmaceutical synthesis, effectively bridging the gap between heterogeneous catalysis and pharmaceutical chemistry.
期刊介绍:
The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies.
The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry:
Liebigs Annalen
Bulletin des Sociétés Chimiques Belges
Bulletin de la Société Chimique de France
Gazzetta Chimica Italiana
Recueil des Travaux Chimiques des Pays-Bas
Anales de Química
Chimika Chronika
Revista Portuguesa de Química
ACH—Models in Chemistry
Polish Journal of Chemistry.