Tetrahedron Green Chem最新文献

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Advanced approach to O-alkyl/aryl salicylaldehyde derivatives: Synthesis, characterization, and free-radical homopolymerization for improved thermal stability

Tetrahedron Green Chem

Pub Date : 2025-03-05 DOI: 10.1016/j.tgchem.2025.100072

Aashna Perwin, Nasreen Mazumdar

In the development of bioactive materials centered around salicylaldehyde, we synthesized O-alkyl/aryl derivatives through the etherification of the phenolic group. Salicylaldehyde underwent a copper-catalyzed reaction with various halides under basic conditions, yielding 2-(3-chloropyrazin-2-yl)oxy benzaldehyde, 2-(6-chloropyrimidin-4-yl)oxy benzaldehyde, and 3-(2-formylphenoxy)-2-hydroxypropyl methacrylate. Meanwhile, 2-(2-formylphenoxy)ethyl methacrylate was synthesized via a sonication-assisted Mitsunobu reaction, affording high yields of ether derivatives. Structural elucidation was achieved using standard analytical techniques, such as ¹H NMR, ¹³C NMR, FT-IR and LC-MS. The free radical homopolymerization of 3-(2-formylphenoxy)-2-hydroxypropyl methacrylate using benzoyl peroxide as an initiator was successfully achieved. The resulting polymer exhibited enhanced thermal stability, as confirmed by solid-state ¹³C NMR, FT-IR, TGA, DSC, and SEM analyses, with a higher glass transition temperature than the reported poly(glycidyl methacrylate). This increase in T_g is attributed to the enhanced rigidity introduced by the aromatic ring in the homopolymer. This study highlights the successful synthesis of various O-alkyl/aryl salicylaldehyde derivatives using different techniques and functionalities, followed by the effective polymerization of one of the monomers, 3-(2-formylphenoxy)-2-hydroxypropyl methacrylate.

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引用次数: 0

Research progress of homogeneous catalytic reactions of hexafluoroisopropanol (HFIP)

Tetrahedron Green Chem

Pub Date : 2025-02-27 DOI: 10.1016/j.tgchem.2025.100071

Huiying Xu, Huidan Luo, Yi Wang, Hui Gao

1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a solvent with unique properties. In recent years, it has received widespread attention due to its ability to stabilize ionic species, transfer protons, and participate in a range of intermolecular interactions, demonstrating excellent benefits in facilitating a variety of challenging chemical reactions. In this review, after a brief introduction to the physical and chemical properties of HFIP in hand, we present examples from the literature representing theoretical studies using HFIP as a solvent in transition metal-, Lewis/Brønsted acid-catalyzed reactions, and homogeneous catalytic reactions (with HFIP itself acting as a catalyst. These examples emphasize the multifunctional role played by HFIP. This indicates that in-depth understanding of its reaction mechanism and performance characteristics is helpful to optimize its application conditions in organic synthesis and improve the efficiency and yield of the reaction. The deep theoretical studies of HFIP in chemical reactions is expected to provide more possibilities and selectivity for the synthesis and application of new compounds.

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引用次数: 0

Valorization of saffron waste as a natural source of 3-hydroxy-γ-butyrolactone, a valuable chiral building block for pharmaceutical applications

Tetrahedron Green Chem

Pub Date : 2025-02-22 DOI: 10.1016/j.tgchem.2025.100069

M. Corti , S. Princiotto , M. Zuccolo , G. Beretta , S. Dallavalle , A. Pinto , F. Annunziata , G. Borgonovo

Saffron is the most expensive spice, appreciated in the best cuisine all over the world. However, its production is connected to the generation of a high volume of waste, i.e. stamens, leaves, tepals, spathes, corm, and tunics. Several biologically active compounds and high value chemical have been identified in the saffron biomass extracts, among which is found 3-hydroxy-γ-butyrolactone (3-HBL), a chiral building block involved in the production of different active pharmaceutical ingredients. The development of the first green and scalable extractive methodology for the isolation of 3-HBL from saffron tepals and stamen could be of great interest for different chemical sectors. After the selection of the best extractive medium (ethyl acetate) and the optimization of the operative procedure to a two-step protocol, microwave assisted extraction and accelerated solvent extraction were compared. The results showed a 3.6 ± 0.2 % vs 2.1 ± 0.1 % w/w recovery and could be exploitable not only on a lab scale but also for a possible industrial application. An enantiomeric excess of 14 % of the (S)-(−) isomer was found.

藏红花是最昂贵的香料，在世界各地的顶级美食中都备受青睐。然而，藏红花的生产过程中会产生大量的废弃物，如雄蕊、叶片、花被片、花盘、花茎和鳞茎。在藏红花生物质提取物中发现了多种生物活性化合物和高价值化学物质，其中包括 3-羟基-γ-丁内酯（3-HBL），这是一种手性结构单元，可用于生产不同的活性药物成分。开发第一种从藏红花花被片和雄蕊中分离 3-HBL 的绿色、可扩展萃取方法，对不同的化学领域具有重大意义。在选择了最佳萃取介质（乙酸乙酯）并将操作程序优化为两步法后，对微波辅助萃取和加速溶剂萃取进行了比较。结果显示，两者的湿重回收率分别为 3.6 ± 0.2 % 和 2.1 ± 0.1 %，不仅可用于实验室规模，也可用于工业应用。发现(S)-(-)异构体的对映体过量率为 14%。

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引用次数: 0

Protecting group-free photocatalyzed O-arylation of quinic acid

Tetrahedron Green Chem

Pub Date : 2025-02-22 DOI: 10.1016/j.tgchem.2025.100070

Miguel A. Bárbara , Nuno R. Candeias , Luis F. Veiros , Filipe Menezes , Andrea Gualandi , Pier G. Cozzi , Carlos A.M. Afonso

This study presents a novel and environmentally friendly approach to the preparation of quinic acid-derived esters from photocatalyzed O-arylation with haloarenes. This study expands the quinic acid-derived chemical space from renewable biomass by harnessing the power of visible-light-driven photocatalysis under mild conditions without the need for protecting groups. A thorough screening of reaction conditions, including the choice of photocatalyst, solvent, base, nickel source, and ligand, led to the identification of the most effective conditions, these being 5CzBN as the optimal photocatalyst, and glyme-based nickel complexes as the preferred nickel source. These conditions enabled the formation of O-arylated products with good yields without noticeable formation of decarboxylated products. Computational calculations support the proposed mechanism for the O-arylation process, based on oxidative addition, anion exchange, and reductive elimination upon energy transfer from the photocatalyst to the Ni(II) species. Computational considerations for a nickel-catalyzed photodecarboxylative arylation mechanism suggest that the oxidation of quinate by the excited photocatalyst or other species derived thereof is considerably less favorable than a pathway only involving energy transfer to a nickel species. The research provides valuable insights into the mechanism of this environmentally conscious transformation.

{"title":"Protecting group-free photocatalyzed O-arylation of quinic acid","authors":"Miguel A. Bárbara , Nuno R. Candeias , Luis F. Veiros , Filipe Menezes , Andrea Gualandi , Pier G. Cozzi , Carlos A.M. Afonso","doi":"10.1016/j.tgchem.2025.100070","DOIUrl":"10.1016/j.tgchem.2025.100070","url":null,"abstract":"<div><div>This study presents a novel and environmentally friendly approach to the preparation of quinic acid-derived esters from photocatalyzed <em>O</em>-arylation with haloarenes. This study expands the quinic acid-derived chemical space from renewable biomass by harnessing the power of visible-light-driven photocatalysis under mild conditions without the need for protecting groups. A thorough screening of reaction conditions, including the choice of photocatalyst, solvent, base, nickel source, and ligand, led to the identification of the most effective conditions, these being 5CzBN as the optimal photocatalyst, and glyme-based nickel complexes as the preferred nickel source. These conditions enabled the formation of <em>O</em>-arylated products with good yields without noticeable formation of decarboxylated products. Computational calculations support the proposed mechanism for the <em>O</em>-arylation process, based on oxidative addition, anion exchange, and reductive elimination upon energy transfer from the photocatalyst to the Ni(II) species. Computational considerations for a nickel-catalyzed photodecarboxylative arylation mechanism suggest that the oxidation of quinate by the excited photocatalyst or other species derived thereof is considerably less favorable than a pathway only involving energy transfer to a nickel species. The research provides valuable insights into the mechanism of this environmentally conscious transformation.</div></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"5 ","pages":"Article 100070"},"PeriodicalIF":0.0,"publicationDate":"2025-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143563344","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

Electrosynthesis of benzimidazole-fused quinazolinones via a cascade addition-desulfurization-cyclization process

Tetrahedron Green Chem

Pub Date : 2025-02-07 DOI: 10.1016/j.tgchem.2025.100068

Khuyen Thu Nguyen , Mongkol Sukwattanasinitt , Sumrit Wacharasindhu

The electrosynthesis of benzimidazole-fused quinazolinones from N-substituted o-phenylenediamines and isothiocyanates via a cascade addition-desulfurization-cyclization process was introduced. This electrochemical approach utilizes the mild and efficient non-metal oxidizing agent, NaI in sub-stoichiometric amounts as an electrolyte/mediator under open-flask conditions. A variety of benzimidazole-fused quinazolinones were prepared in moderate to excellent yields (30–98 %, 10 examples). Additionally, the optimal conditions were successfully applied to the synthesis of benzoxazoloquinazolinones and benzothiazolquinazolinones (30–72 %, 6 examples). This electrochemical process is scalable, while maintaining reaction efficiency even at the gram scale.

引用次数: 0

Synthesis and characterization of SnS2 nanoparticles for enhanced photocatalytic and electrochemical sensing applications

Tetrahedron Green Chem

Pub Date : 2025-02-05 DOI: 10.1016/j.tgchem.2025.100067

Sumanjali Kota , Akshay Shivashankar , Tushvitha Dhayakaran , Uthkruthi Munegowda , Bharath K. Devendra

This study presents a straightforward, cost-effective method for synthesizing Tin Sulfide (SnS₂) nanoparticles using magnetic stirring. The prepared SnS₂ was analyzed using XRD, FESEM, EDAX, UV–Vis, FTIR, XPS, HRTEM, and SAED analysis. The photodegradation of Methyl Violet (MV) dye achieved a 93.8 % decolourization rate within 120 min, following first-order kinetic reaction rates. The half-life (t1/2) was determined to be 31.18 min, and the stability of the photocatalyst was evaluated under different pH conditions. Cyclic Voltammetry (CV) studies were performed using a carbon paste electrode in 2 M KOH, revealing a low electrochemical value and proton diffusion coefficient for SnS₂, indicating good redox behaviour with a C_sp of approximately 158 F/g. The electrochemical sensing of urea demonstrated excellent performance with the SnS₂ electrode. Additionally, the sensor's pH response was investigated under three different pH conditions, showing remarkable urea sensing capabilities influenced by pH and electrolyte environment.

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引用次数: 0

Laccase cataylzed synthesis of quaternary malononitriles with an aryl substituent

Tetrahedron Green Chem

Pub Date : 2025-01-26 DOI: 10.1016/j.tgchem.2025.100066

Parisa Amani, Mansour Shahedi, Elaheh Rezaei, Zohreh Habibi

Synthesis of quaternary malononitriles with an aryl substituent is of great importance because these scaffolds serve as essential intermediates in the synthesis of bioactive compounds. This study presents an efficient method for the laccase-catalyzed arylation of 2-substituted malononitrile derivatives by oxidation of catechols using aerial oxygen as the oxidant, followed by the nucleophilic addition of 2-substituted malononitriles. The process achieves yields ranging from moderate to excellent (73–97 %), and also, it was associated with a slight decrease in efficiency in higher scales.

引用次数: 0

A review on synthesis of β-amino carbonyl compounds using nanocatalyst

Tetrahedron Green Chem

Pub Date : 2025-01-25 DOI: 10.1016/j.tgchem.2025.100065

Satyaranjan Behera

Nanomaterials have piqued researchers' interest in various fields due to their extraordinary advantages, which include a large surface area. The use of nanomaterials in catalysis is a hot issue for researchers. Catalysis plays a vital role in the synthesis of medicinal as well as pharmaceutical compounds. Pharmaceutical chemicals, including β-amino carbonyl compounds and their derivatives, are commonly used as synthetic intermediates in manufacturing natural products, pharmaceuticals, physiologically active molecules, and medicines. Synthesis of β-amino carbonyl compounds involves many processes, including Mannich and aza-Michael reactions. The synthesis of β-amino carbonyl compounds remains challenging for chemists due to their severe side products. Researchers have now used nanocatalysts to achieve clean and smooth reactions, high purity of products, and reusability. Due to high surface area, nanocatalysts have tremendous catalytic activity. Nowadays many modified nanocatalyst have been developed to produce high yields of the products. The present review described the synthesis of β-amino carbonyl compounds by using different nanocatalysts reported to date.

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引用次数: 0

Catalytic macrocyclization of unactivated C(sp3)-H bond in natural product synthesis

Tetrahedron Green Chem

Pub Date : 2025-01-18 DOI: 10.1016/j.tgchem.2025.100064

Zhuo Wang

Macrocyclic natural products present as essential scaffolds in drug development. Excited by the biological properties of macrocyclic natural products, its synthesis and the development of macrocyclization methods is an important research area in organic and medicinal chemistry. In particular, macrocyclization preparing macrocyclic structures via catalytic functionalization of unactivated C(sp³)-H bonds is increasingly prevalent in the literature. Here, we provide a minireview highlighting the contemporary advancements of catalytic macrocyclization of unactivated C(sp³)-H bond in method developments and natural product synthesis. Representative examples from 2017 to 2024 are discussed.

引用次数: 0

Selective synthesis of phosphate mono-esters with an acidic modified niobium oxide catalyst

Tetrahedron Green Chem

Pub Date : 2025-01-16 DOI: 10.1016/j.tgchem.2025.100063

Jens Wéry, Sofia Radelicki, Thomas J.N. Hooper, Margot Houbrechts, Kwinten Janssens, Wouter Stuyck, Dimitrios Sakellariou, Dirk E. De Vos

The atom-efficient esterification of phosphoric acid was investigated for the selective synthesis of phosphate mono-esters using an acid treated niobium oxide catalyst, avoiding the use of amines as is common in literature. Kinetic studies revealed that the heterogeneous catalyst exhibited higher selectivity for mono-esters compared to homogeneous acid catalysts, as supported by calculation of the relative reactivity of mono-ester and phosphoric acid with different catalysts. To characterize the catalyst, its Hammett acidity value (H₀) was determined, while solid state ³¹P NMR enabled studying the adsorption of H₃PO₄. Due to the mild acidity of the niobium oxide, alcohols with acid-sensitive functions, including substituted double bonds, could be phosphorylated, enabling the synthesis of surfactants such as oleyl phosphate.

引用次数: 0

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