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Revisiting the role of sulfated oxides for the synthesis of pharmaceutically important heterocycles: Understanding, challenges, and future prospects 回顾硫酸氧化物在合成重要杂环化合物中的作用:认识、挑战和未来展望
Tetrahedron Green Chem Pub Date : 2023-12-01 Epub Date: 2023-11-30 DOI: 10.1016/j.tgchem.2023.100031
Sandeep S. Kahandal , Anand S. Burange , Thomson A. Fernandes
{"title":"Revisiting the role of sulfated oxides for the synthesis of pharmaceutically important heterocycles: Understanding, challenges, and future prospects","authors":"Sandeep S. Kahandal ,&nbsp;Anand S. Burange ,&nbsp;Thomson A. Fernandes","doi":"10.1016/j.tgchem.2023.100031","DOIUrl":"https://doi.org/10.1016/j.tgchem.2023.100031","url":null,"abstract":"<div><p>The development of sustainable catalytic processes is the requirement of the future to replace traditional protocols involving hazardous, non-green, non-benign reagents/solvents, and cost ineffectiveness. Metal and mixed metal oxides due to their redox properties make them potential substitutes for conventional homogeneous catalysts. The acidity can be enhanced further by the sulfation process to form sulfated oxides representing a new class of solid acid catalysts. This review is the revisiting of sulfated solid acid catalysts, with major emphasis on understanding, methods, applications, and their role in the syntheses of heterocycles of pharmaceutical importance. The present review also discusses factors affecting the acidity of the catalysts, possibilities of leaching in reaction media, methods of sulfation to arrest leaching, other challenges, and future prospects.</p></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"2 ","pages":"Article 100031"},"PeriodicalIF":0.0,"publicationDate":"2023-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2773223123000304/pdfft?md5=f2e74ebfdbd3647971a2dae49c49a600&pid=1-s2.0-S2773223123000304-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138474762","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Manganese-catalysed C2 allylation and deuteration of indoles in water 锰催化C2烯丙化和水中吲哚的氘化
Tetrahedron Green Chem Pub Date : 2023-12-01 Epub Date: 2023-07-16 DOI: 10.1016/j.tgchem.2023.100019
Si Lok Ko , Eimear Courtney , Dr Mark Light , Dr David Jones , Dr Gerard P. McGlacken
{"title":"Manganese-catalysed C2 allylation and deuteration of indoles in water","authors":"Si Lok Ko ,&nbsp;Eimear Courtney ,&nbsp;Dr Mark Light ,&nbsp;Dr David Jones ,&nbsp;Dr Gerard P. McGlacken","doi":"10.1016/j.tgchem.2023.100019","DOIUrl":"https://doi.org/10.1016/j.tgchem.2023.100019","url":null,"abstract":"<div><p>Mn-catalysed C–H activation has emerged as a useful sustainable methodology for the formation of new C–C bonds. To date most of the protocols are described in organic solvents. Water as solvent, on the other hand, would be highly advantageous, but is often incompatible with organometallic chemistry. Herein, we describe the C–H activation of indoles using an unmodified, commercially available manganese catalyst in water. Two types of valuable allyl groups can be added and a good substrate scope is described. Substitution at the C-3 group is tolerated, allowing access to medicinally important frameworks, and the reaction works on a gram scale. Finally, harnessing the tolerance of water as the reaction medium, D<sub>2</sub>O can be used as an inexpensive source of deuterium for the C-2 labelling of indoles.</p></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"2 ","pages":"Article 100019"},"PeriodicalIF":0.0,"publicationDate":"2023-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49707422","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Visible light-promoted metal-free aerobic photooxidation of xanthenes, thioxanthenes and dihydroacridines in deep eutectic solvents 可见光促进深共晶溶剂中杂蒽、硫杂蒽和二氢吖啶的无金属有氧光氧化
Tetrahedron Green Chem Pub Date : 2023-12-01 Epub Date: 2023-11-14 DOI: 10.1016/j.tgchem.2023.100030
Sarah-Jayne Burlingham, Alejandro Torregrosa-Chinillach, Diego A. Alonso, Rafael Chinchilla
{"title":"Visible light-promoted metal-free aerobic photooxidation of xanthenes, thioxanthenes and dihydroacridines in deep eutectic solvents","authors":"Sarah-Jayne Burlingham,&nbsp;Alejandro Torregrosa-Chinillach,&nbsp;Diego A. Alonso,&nbsp;Rafael Chinchilla","doi":"10.1016/j.tgchem.2023.100030","DOIUrl":"10.1016/j.tgchem.2023.100030","url":null,"abstract":"<div><p>Benzylic systems such as 9<em>H</em>-xanthenes, 9<em>H</em>-thioxanthenes and 9,10-dihydroacridines can be easily oxidized to the corresponding xanthones, thioxanthones or acridones, respectively, in deep eutectic solvents by a visible blue light-promoted photooxidation procedure carried out using ambient air as oxidant in the presence of riboflavin tetraacetate as a metal-free photocatalyst. The obtained yields are high or almost quantitative, and the reaction media can be recovered and reused. The environmental friendliness of the protocol is demonstrated based on several green metrics.</p></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"2 ","pages":"Article 100030"},"PeriodicalIF":0.0,"publicationDate":"2023-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2773223123000298/pdfft?md5=838cc1e591a9a4ce9fe4d15eda184782&pid=1-s2.0-S2773223123000298-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135763446","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Valorisation of terpenes by continuous flow hydrogenation over 3D-printed Palladium catalysts 3d打印钯催化剂上连续流动加氢对萜烯的增值作用
Tetrahedron Green Chem Pub Date : 2023-12-01 Epub Date: 2023-06-21 DOI: 10.1016/j.tgchem.2023.100014
Ivan Martinez-Botella, Stuart Littler, Milan Kundra, Christian H. Hornung
{"title":"Valorisation of terpenes by continuous flow hydrogenation over 3D-printed Palladium catalysts","authors":"Ivan Martinez-Botella,&nbsp;Stuart Littler,&nbsp;Milan Kundra,&nbsp;Christian H. Hornung","doi":"10.1016/j.tgchem.2023.100014","DOIUrl":"https://doi.org/10.1016/j.tgchem.2023.100014","url":null,"abstract":"<div><p>The hydrogenation of the monoterpene β-myrcene, the sesquiterpene farnesene and the triterpene squalene was studied in a custom-built continuous flow reactor using 3D printed stainless steel static mixers coated with Palladium catalyst. Full hydrogenation was achieved in a facile and cost-effective fashion using Catalytic Static Mixer (CSM) technology. Wash coated Pd/Al<sub>2</sub>O<sub>3</sub> CSMs for the hydrogenation of β-myrcene in ethyl acetate and electroplated Pd CSMs proved to be efficient for the hydrogenation of farnesene and squalene in solvent-free reactions to produce the fully hydrogenated terpenes 2,6-dimethyloctane, farnesane and squalane.</p></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"2 ","pages":"Article 100014"},"PeriodicalIF":0.0,"publicationDate":"2023-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49766854","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Heterogeneous flow chemistry through bamboo-based microfluidic reactors 竹材基微流控反应器的非均相流动化学研究
Tetrahedron Green Chem Pub Date : 2023-12-01 Epub Date: 2023-08-12 DOI: 10.1016/j.tgchem.2023.100022
Omar Ginoble Pandoli
{"title":"Heterogeneous flow chemistry through bamboo-based microfluidic reactors","authors":"Omar Ginoble Pandoli","doi":"10.1016/j.tgchem.2023.100022","DOIUrl":"https://doi.org/10.1016/j.tgchem.2023.100022","url":null,"abstract":"<div><p>The rapid development of flow chemistry and its related microfluid technology has accelerated the innovation in material science and the research into alternative, environmentally, and cost-effective microfabrication procedures. This article reviews the latest advances in bamboo-based microfluidic devices, highlighting the heterogeneous catalysis in flow mode through the three-dimensional (3D) structures of the plant's vascular bundles. Different strategies for immobilizing catalysts (metal and enzymes) and the design of the lignocellulosic-based flow reactor are presented.</p></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"2 ","pages":"Article 100022"},"PeriodicalIF":0.0,"publicationDate":"2023-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49766860","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recoverable and reusable heterogeneous yttrium triflate for michael and diels-alder additions 可回收和可重复使用的异质三氧化钇，用于迈克尔和迪尔斯-阿尔德添加法
Tetrahedron Green Chem Pub Date : 2023-12-01 Epub Date: 2023-11-30 DOI: 10.1016/j.tgchem.2023.100032
Emanuela Donato, Fabrizio Medici, Valerio Chiroli, Sergio Rossi, Alessandra Puglisi
{"title":"Recoverable and reusable heterogeneous yttrium triflate for michael and diels-alder additions","authors":"Emanuela Donato,&nbsp;Fabrizio Medici,&nbsp;Valerio Chiroli,&nbsp;Sergio Rossi,&nbsp;Alessandra Puglisi","doi":"10.1016/j.tgchem.2023.100032","DOIUrl":"https://doi.org/10.1016/j.tgchem.2023.100032","url":null,"abstract":"","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"2 ","pages":"Article 100032"},"PeriodicalIF":0.0,"publicationDate":"2023-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2773223123000316/pdfft?md5=0183217b7f0e07a9ae602629fe1aa42f&pid=1-s2.0-S2773223123000316-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138549445","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Development and characterization of a continuous ultrasound emulsification and nano-emulsion polymerization process 连续超声乳化与纳米乳液聚合工艺的开发与表征
Tetrahedron Green Chem Pub Date : 2023-12-01 Epub Date: 2023-08-12 DOI: 10.1016/j.tgchem.2023.100023
Jonas Loncke , Arne Vancleef , Wim Dermaut , Leen Braeken , Leen C.J. Thomassen
{"title":"Development and characterization of a continuous ultrasound emulsification and nano-emulsion polymerization process","authors":"Jonas Loncke ,&nbsp;Arne Vancleef ,&nbsp;Wim Dermaut ,&nbsp;Leen Braeken ,&nbsp;Leen C.J. Thomassen","doi":"10.1016/j.tgchem.2023.100023","DOIUrl":"https://doi.org/10.1016/j.tgchem.2023.100023","url":null,"abstract":"<div><p>Typically, nano-emulsions are prepared in batch high-speed homogenization or ultrasound processes and polymerized afterwards in batch reactors. However, fully continuous processes have the potential to decrease production costs and energy consumption compared to batch processes. This research thus focuses on implementing ultrasound into a fully continuous emulsification and nano-emulsion polymerization process to obtain latex nano-particles from butylmethacrylate and ethylene glycol dimethacrylate. The goal of this research is to produce nano-emulsions and nano-particles with the smallest obtainable size and polydispersity in a fully continuous two-stage process. In the first stage or emulsification stage, parameters like flowrate, residence time and acoustic power are varied to influence and determine the optimal energy density. In second stage or reaction stage, residence time and reaction temperature are studied to obtain particles of monodisperse sizes. Samples produced in both stages are analysed with Dynamic Light Scattering to measure the average size and polydispersity (PdI) of the emulsion droplets and particles. Emulsification results indicate that droplet size and PdI decreases at increasing energy densities (J/ml) until 60 J/ml after which a constant droplet size of 150 nm and PdI of 0.230 are reached. Furthermore, a particle size of 50 nm and PdI of 0.080 were achieved in both batch and continuous polymerization reactors after 5 min at 85 °C. By implementing the most optimal process parameters, small emulsion droplets and particles were obtained more energy efficient in a shorter emulsification and reaction time compared to literature ultrasound assisted nano-emulsion polymerization processes.</p></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"2 ","pages":"Article 100023"},"PeriodicalIF":0.0,"publicationDate":"2023-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49707426","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A green deprotection strategy: Removing acid-labile protecting groups using lemon juice/ethanol as the solvent 绿色去保护策略:用柠檬汁/乙醇作为溶剂去除酸不稳定的保护基团
Tetrahedron Green Chem Pub Date : 2023-12-01 Epub Date: 2023-08-18 DOI: 10.1016/j.tgchem.2023.100026
Weiding Wang, Yinzhe Chen, Xiaoheng Li, Qian Zhang
{"title":"A green deprotection strategy: Removing acid-labile protecting groups using lemon juice/ethanol as the solvent","authors":"Weiding Wang,&nbsp;Yinzhe Chen,&nbsp;Xiaoheng Li,&nbsp;Qian Zhang","doi":"10.1016/j.tgchem.2023.100026","DOIUrl":"https://doi.org/10.1016/j.tgchem.2023.100026","url":null,"abstract":"<div><p>Lemon juice has been studied and reported as an efficient catalyst or green medium in organic synthesis. The present digest paper shows the successful and efficient Removal of multiple acid-labile protecting groups using crude lemon juice for the first time. Several drops of lemon juice can rapidly convert some simple liquid acetals to carbonyl compounds. Also, when mixed with ethanol, lemon juice effectively removes cyclic acetals and other protection groups on primary or secondary alcohols. In addition, for the selective Removal of acetonide on diacetone-<span>d</span>-glucose and its derivatives, the yield can reach more than 85%. Lemon juice, combined with ethanol as a solvent, can avoid using hazardous organic or inorganic acids to remove acid-labile protecting groups while being environmentally friendly.</p></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"2 ","pages":"Article 100026"},"PeriodicalIF":0.0,"publicationDate":"2023-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49707675","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Role of organic solvent and influence of oxidant in the oxidation of linalool catalyzed by molybdenum and vanadium complexes 有机溶剂在钼钒配合物催化芳樟醇氧化中的作用及氧化剂的影响
Tetrahedron Green Chem Pub Date : 2023-12-01 Epub Date: 2023-10-01 DOI: 10.1016/j.tgchem.2023.100029
Ali Al Hadi Haidar , Dominique Agustin
{"title":"Role of organic solvent and influence of oxidant in the oxidation of linalool catalyzed by molybdenum and vanadium complexes","authors":"Ali Al Hadi Haidar ,&nbsp;Dominique Agustin","doi":"10.1016/j.tgchem.2023.100029","DOIUrl":"https://doi.org/10.1016/j.tgchem.2023.100029","url":null,"abstract":"<div><p>The coordination complexes [MoO<sub>2</sub>(SAP)]<sub>2</sub> [<strong>Mo</strong>] and [VO(SAP)]<sub>2</sub>O [<strong>V</strong>] (SAP = salicylideneamino-phenolato) were tested as pre-catalysts for oxidation of a biomass-issued substrate, linalool (<strong>L</strong>). The reaction was studied using different oxidants, TBHP (in water or in decane) or H<sub>2</sub>O<sub>2</sub> (in water with/without acetonitrile). Efficient linalool (<strong>L</strong>) conversions were obtained with selectivity towards two selected products, 2-(5-methyl-5- vinyltetrahydro-furan-2-yl propan-2-ol) (<strong>1</strong>) and 2,2,6- trimethyl-6-vinyltetrahydro-2H-pyran-3-ol (<strong>2</strong>) depending on pre-catalysts and oxidant. Green metrics have been calculated and showed the role of organic solvent for the process.</p></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"2 ","pages":"Article 100029"},"PeriodicalIF":0.0,"publicationDate":"2023-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49766852","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A short review: Chemo-catalytic CO2 insertion in amine and amino alcohols to produce linear and cyclic carbamates 化学催化CO2插入胺和氨基醇制备线性和环状氨基甲酸酯的研究进展
Tetrahedron Green Chem Pub Date : 2023-12-01 Epub Date: 2023-09-04 DOI: 10.1016/j.tgchem.2023.100024
Sharda Kondawar , Chetana Patil , Sadhana Raylu , Chandrashekhar Rode
{"title":"A short review: Chemo-catalytic CO2 insertion in amine and amino alcohols to produce linear and cyclic carbamates","authors":"Sharda Kondawar ,&nbsp;Chetana Patil ,&nbsp;Sadhana Raylu ,&nbsp;Chandrashekhar Rode","doi":"10.1016/j.tgchem.2023.100024","DOIUrl":"https://doi.org/10.1016/j.tgchem.2023.100024","url":null,"abstract":"<div><p>The adverse effect of carbon dioxide occurred in past decade on environment, led researchers to use CO<sub>2</sub> as a C1 building block for the synthesis of various commodity chemicals. Most of the drug molecules and polymers have back bone of carbon chain which provides great opportunity to researchers, to make use of CO<sub>2</sub> as an abundant and renewable source of carbon. Chemo-catalytic synthesis of industrially important cyclic and open chain carbamate using amino alcohol/alcohol and amine in presence of CO<sub>2</sub> as carbonylating agent has got much more attention in recent years. This review focuses on the literature survey from 1986 to 2022 on carbamate synthesis and provides clear idea about prerequisite active sites in catalyst for the activation of CO<sub>2</sub> which is a major challenge. The details of mechanism proposed for the chemo-catalytic pathway has been discussed in detail in order to understand and design the novel and efficient catalyst system in near future in this demanding research field.</p></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"2 ","pages":"Article 100024"},"PeriodicalIF":0.0,"publicationDate":"2023-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49760884","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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