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Photocatalytic C–C bond formation and cleavage reactions based on graphitic carbon nitride semiconductor materials
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-07 DOI: 10.1016/j.tet.2025.134651
Wenjie Zhang, Zeyao Liang, Xiaoquan Yao
{"title":"Photocatalytic C–C bond formation and cleavage reactions based on graphitic carbon nitride semiconductor materials","authors":"Wenjie Zhang,&nbsp;Zeyao Liang,&nbsp;Xiaoquan Yao","doi":"10.1016/j.tet.2025.134651","DOIUrl":"10.1016/j.tet.2025.134651","url":null,"abstract":"<div><div>Graphitic carbon nitride (g-C<sub>3</sub>N<sub>4</sub>) materials, owing to their unique electronic band structure, high chemical stability, and visible light response characteristics, have demonstrated significant potential in photocatalytic organic synthesis reactions in recent years. Through modification strategies such as structural tuning, elemental doping, and construction of heterojunctions, the light absorption capacity of g-C<sub>3</sub>N<sub>4</sub> can be effectively enhanced, which promotes the efficient separation and transfer of photogenerated carriers, thereby improving the efficiency of photocatalytic reactions. This review aims to summarize the research progress on graphitic carbon nitride and carbon nitride materials modified by structural tuning, elemental doping, metal loading and heterojunctions construction as photocatalysts in C–C single bond formation and cleavage reactions.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134651"},"PeriodicalIF":2.1,"publicationDate":"2025-04-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143799856","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Total solid-phase synthesis and structural elucidation of sovateltide
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-05 DOI: 10.1016/j.tet.2025.134650
Ajit Hanumant Chandgude , Ravinder Reddy Patlolla , Jayvant Harlikar , Linga Banoth
{"title":"Total solid-phase synthesis and structural elucidation of sovateltide","authors":"Ajit Hanumant Chandgude ,&nbsp;Ravinder Reddy Patlolla ,&nbsp;Jayvant Harlikar ,&nbsp;Linga Banoth","doi":"10.1016/j.tet.2025.134650","DOIUrl":"10.1016/j.tet.2025.134650","url":null,"abstract":"<div><div>Sovateltide (IRL-1620, PMZ-1620), a synthetic endothelin-1 analog, is a promising therapeutic agent for acute ischemic stroke. This study details the total solid-phase Peptide synthesis (SPPS) of Sovateltide and its subsequent structural elucidation. SPPS relies on the repetitive cycles of deprotection, coupling, and washing the 14-amino acid peptide chain on a solid support. Following cleavage from the resin and deprotection of side chain functionalities, Sovateltide was purified to homogeneity using preparative high-performance liquid chromatography (Prep HPLC). The Sovateltide successful synthesis and purification was achieved with overall yields∼28 % and product purity of ≥98 % at 13.8 mmol scale. Structural confirmation was achieved using mass spectrometry, NMR, and CD spectroscopy analysis. LCMS analysis confirmed the amino acid sequence, while 2D NMR data validated its structure. The secondary structure estimation was confirmed through CD spectroscopy.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134650"},"PeriodicalIF":2.1,"publicationDate":"2025-04-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143830430","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Advances in transition metal-catalyzed hydroamination of strained ring systems: A comprehensive review
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-05 DOI: 10.1016/j.tet.2025.134652
Anns Maria Thomas , Amrutha P. Thankachan , Gopinathan Anilkumar
{"title":"Advances in transition metal-catalyzed hydroamination of strained ring systems: A comprehensive review","authors":"Anns Maria Thomas ,&nbsp;Amrutha P. Thankachan ,&nbsp;Gopinathan Anilkumar","doi":"10.1016/j.tet.2025.134652","DOIUrl":"10.1016/j.tet.2025.134652","url":null,"abstract":"<div><div>This review focuses exclusively on the transition metal-catalyzed hydroamination of strained ring including methylene cyclopropanes, cyclopropenes, cyclobutenes, and norbornenes. Hydroamination comprises the addition of an amine across a carbon-carbon unsaturated bond, resulting in the formation of a new carbon-nitrogen bond. Among the transition metals, Palladium, Copper, and Gold are now being extensively investigated for these reactions. The reactions catalyzed by other transition metals like Co, Ag, Ti, Ir, Rh, etc. are still in the juvenile stage. Intramolecular hydroaminations are generally faster and more versatile than intermolecular processes, with the latter often facing challenges related to regio- and stereoselectivity. This review systematically classifies advancements based on catalytic systems, providing insights into reaction mechanisms, synthetic methodologies, and potential applications. A comprehensive survey of literature from 1988 to 2024 has been conducted to present an in-depth analysis of this field.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134652"},"PeriodicalIF":2.1,"publicationDate":"2025-04-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143830428","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Palladium-catalyzed chemoselective N-monoallylation of aromatic amines with diallylamine through a borrowing hydrogen strategy
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-04 DOI: 10.1016/j.tet.2025.134648
Chengcheng Fang , Jie-Qing Ou , Xiaoye Mo , Yingqian Xu , Sifeng Li
{"title":"Palladium-catalyzed chemoselective N-monoallylation of aromatic amines with diallylamine through a borrowing hydrogen strategy","authors":"Chengcheng Fang ,&nbsp;Jie-Qing Ou ,&nbsp;Xiaoye Mo ,&nbsp;Yingqian Xu ,&nbsp;Sifeng Li","doi":"10.1016/j.tet.2025.134648","DOIUrl":"10.1016/j.tet.2025.134648","url":null,"abstract":"<div><div>A palladium-catalyzed <em>N</em>-monoallylation reaction of aromatic amines with diallylamine at relatively low temperatures has been established for the synthesis of <em>N</em>-monoallylated amines <em>via</em> a borrowing hydrogen strategy. Employing diallylamine as the allylating agent, primary (hetero)aryl amines, <em>N</em>-alkyl secondary (hetero)aryl amines, <em>N</em>,<em>N</em>-diarylamines, and various commercially available aniline-containing pharmaceuticals can be utilized to synthesize <em>N</em>-monoallyl aromatic amines with releasing ammonia as the by-product.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134648"},"PeriodicalIF":2.1,"publicationDate":"2025-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143799858","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Optimised synthesis of florzolotau and its fluorine-18 radiolabelling precursor 氟唑陶及其氟-18 辐射标记前体的优化合成
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-04 DOI: 10.1016/j.tet.2025.134649
Andrew P. Montgomery , Edward D. Harvey-Latham , Michael Kassiou, Jonathan J. Danon
{"title":"Optimised synthesis of florzolotau and its fluorine-18 radiolabelling precursor","authors":"Andrew P. Montgomery ,&nbsp;Edward D. Harvey-Latham ,&nbsp;Michael Kassiou,&nbsp;Jonathan J. Danon","doi":"10.1016/j.tet.2025.134649","DOIUrl":"10.1016/j.tet.2025.134649","url":null,"abstract":"<div><div>Diverse neurodegenerative disorders that are neuropathologically characterised by depositions of tau protein aggregates are collectively referred to as tauopathies. This can include diseases such as Alzheimer's disease (AD), frontotemporal lobar degeneration and progressive supranuclear palsy. Tauopathies are classified according to the relative ratio of tau protein isoforms (3R or 4R) that make up their aggregates. Positron emission tomography (PET) enables the visualisation of tau lesions <em>in vivo</em>, but imaging both 3R and 4R deposits with the same imaging agent is an ongoing challenge. An emerging tau PET radiotracer, [<sup>18</sup>F]-florzolotau (also known as [<sup>18</sup>F]PM-PBB3 or [<sup>18</sup>F]APN-1607), reportedly binds to all tau isoforms, making it a clinically useful tool for assessing disease pathology in patients with both 3R and 4R tauopathies. In this work, we report for the first time a complete, convergent synthesis of a radiolabelling precursor of [<sup>18</sup>F]-florzolotau and its non-radioactive reference standard from commercially available starting materials. We demonstrate the scalability of our approach to facilitate wider access to this clinically useful imaging agent.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134649"},"PeriodicalIF":2.1,"publicationDate":"2025-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143786230","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Highly diastereodivergent green synthesis of cyclohexanones via double Michael addition of malononitrile to Dibenzalacetone
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-03 DOI: 10.1016/j.tet.2025.134637
Nasiri Behzad, Ashouri Akram
{"title":"Highly diastereodivergent green synthesis of cyclohexanones via double Michael addition of malononitrile to Dibenzalacetone","authors":"Nasiri Behzad,&nbsp;Ashouri Akram","doi":"10.1016/j.tet.2025.134637","DOIUrl":"10.1016/j.tet.2025.134637","url":null,"abstract":"<div><div>The distinct biological activities of stereoisomers make diastereoselective synthesis a pivotal area in organic chemistry, especially following environmentally friendly practices. In this study, a novel green bis-Michael cycloaddition strategy was developed, adhering to multiple principles of green chemistry. Key highlights include using ethanol as the solvent, reaction conditions at room temperature, new cyclohexanone derivatives with good to excellent yield and diastereoselectivity, diastereodivergent, scalability, and simplified purification steps. Optimization studies involving various solvents, bases, and temperatures were conducted to establish the best reaction conditions. Furthermore, the versatility of this method was demonstrated with a range of electron-rich and electron-withdrawing substituents on DiBenzylideneAcetone (DBA) derivatives. Additionally, several transformations were performed to explore the conformations of the resulting products, employing 1D and 2D NMR techniques and mass spectrometry for detailed analysis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134637"},"PeriodicalIF":2.1,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143799857","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Electrophilic thiocyanation of aromatic, heteroaromatic and aliphatic compounds: A novel perspective on recent advances
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-03 DOI: 10.1016/j.tet.2025.134645
Sobhan Rezayati , Maryam Manafi Moghadam , Ali Ramazani , Guoying Zhang
{"title":"Electrophilic thiocyanation of aromatic, heteroaromatic and aliphatic compounds: A novel perspective on recent advances","authors":"Sobhan Rezayati ,&nbsp;Maryam Manafi Moghadam ,&nbsp;Ali Ramazani ,&nbsp;Guoying Zhang","doi":"10.1016/j.tet.2025.134645","DOIUrl":"10.1016/j.tet.2025.134645","url":null,"abstract":"<div><div>One important technique in organic chemistry that makes it easier to create thiocyanate derivatives from aliphatic, aromatic and heteroaromatic molecules is electrophilic thiocyanation. In our earlier article, we explored the foundational concepts and approaches for synthesizing thiocyanates. This study offers a comprehensive and analytical review of the latest advancements in this field. We explore innovative trends, key drivers, and factors influencing the reaction conditions that have enhanced the yield and selectivity of these reactions. Additionally, we examine current research and present fresh ideas that weren't as prominent in our earlier work. Here, we shall categorize a broad range of techniques for the production of aromatic and heteroaromatic thiocyanate derivatives that have been developed over the last four years based on different catalysts. In addition to compiling the body of knowledge, this article helps scholars become acquainted with recent developments in electrophilic thiocyanation and pinpoint areas for further investigation.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134645"},"PeriodicalIF":2.1,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143791505","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthetic reactions using a 3-D printed acid-catalyst 使用 3-D 打印酸催化剂进行合成反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-03 DOI: 10.1016/j.tet.2025.134636
Jacob C. Hood , Niechen Chen , Douglas A. Klumpp
{"title":"Synthetic reactions using a 3-D printed acid-catalyst","authors":"Jacob C. Hood ,&nbsp;Niechen Chen ,&nbsp;Douglas A. Klumpp","doi":"10.1016/j.tet.2025.134636","DOIUrl":"10.1016/j.tet.2025.134636","url":null,"abstract":"<div><div>A 3-D printed cartridge was fabricated using acrylonitrile-butadiene-styrene (ABS) printer filament. The cartridge was printed with an internal helical honeycomb channel pattern - providing a high surface area suitable for flow chemistry. The internal chamber of the cartridge was treated with fuming sulfuric acid to anneal the surface and functionalize the material with sulfonic acid groups. The 3-D printed catalyst was then used in a variety acid-catalyzed organic reactions, with conversions in 52–97 % yields.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134636"},"PeriodicalIF":2.1,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143786231","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Facile synthesis of benzo[e][1,2,4]triazepin-5-ones through a base medicated [4+3] cycloaddition
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-03 DOI: 10.1016/j.tet.2025.134595
Eeda lingareddy , Ravindra M. Kumbhare
{"title":"Facile synthesis of benzo[e][1,2,4]triazepin-5-ones through a base medicated [4+3] cycloaddition","authors":"Eeda lingareddy ,&nbsp;Ravindra M. Kumbhare","doi":"10.1016/j.tet.2025.134595","DOIUrl":"10.1016/j.tet.2025.134595","url":null,"abstract":"<div><div>Herein, we report the synthesis of highly functionalized benzo[e][1,2,4]triazepin-5-ones through a base medicated [4 + 3] cycloaddition of hydrazonoyl chloride and isatoic anhydride. The reaction proceeds through <em>in situ</em> generated nitrile imines from easily accessible hydrazonoyl chlorides. a simple organic base triethyl amine drives the reaction very successfully to give the desired products in excellent yields. The robustness of the [4 + 3] cycloaddition process is well evidented by broad substrate scope.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134595"},"PeriodicalIF":2.1,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143776802","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Oximes and hydrazones as versatile directing groups: A critical review on C–H activation and functionalization
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-03 DOI: 10.1016/j.tet.2025.134634
Adarsh Jha, Sowmya Dastari, Nandini M. Barve, Nagula Shankaraiah
{"title":"Oximes and hydrazones as versatile directing groups: A critical review on C–H activation and functionalization","authors":"Adarsh Jha,&nbsp;Sowmya Dastari,&nbsp;Nandini M. Barve,&nbsp;Nagula Shankaraiah","doi":"10.1016/j.tet.2025.134634","DOIUrl":"10.1016/j.tet.2025.134634","url":null,"abstract":"<div><div>The selective activation of C–H bonds is a crucial step in modern organic synthesis using a variety of directing groups which allows for efficient access to complex molecular frameworks. In this, oximes and hydrazones have emerged as adaptable directing groups (DGs) in facilitating diverse transformations, including the synthesis of quinolines, carbolines, <em>aza</em>-heterocycles, spirocycles, and annulations with C–N bond formation. Beyond serving as co-ordinating moieties, these groups can act as internal oxidants in specific pathways, enhancing the reaction efficiency and selectivity. Owing to their versatility, this review highlights the recent advancements of C–H activation strategies mediated by oxime and hydrazone as facile directing groups. The review also emphasizes their structural diversity and exploration of mechanistic aspects of the reactions. Key applications includes the construction of nitrogen-rich frameworks with broad functional group tolerance. In additions, challenges such as substrate scope, selectivity and potential difficulties using oximes/hydrazones as directing groups are discussed, including innovative and sustainable approaches.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134634"},"PeriodicalIF":2.1,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143816597","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","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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