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Efficient chemoselective sequential Pd-catalyzed Suzuki coupling of highly functionalized iodoaryl triflates 高功能化碘芳基三氟化酯的高效化学选择性序贯pd催化铃木偶联
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-21 DOI: 10.1016/j.tet.2025.134793
Till Schreiner, Philipp Reitinger, Maria Degli Innocenti, Fabian Gruber, Rolf Breinbauer
{"title":"Efficient chemoselective sequential Pd-catalyzed Suzuki coupling of highly functionalized iodoaryl triflates","authors":"Till Schreiner,&nbsp;Philipp Reitinger,&nbsp;Maria Degli Innocenti,&nbsp;Fabian Gruber,&nbsp;Rolf Breinbauer","doi":"10.1016/j.tet.2025.134793","DOIUrl":"10.1016/j.tet.2025.134793","url":null,"abstract":"<div><div>The Pd-catalyzed Suzuki-Miyaura (SM) cross-coupling of aryl halides with organoboron compounds is a widely used tool in organic synthesis for the construction of C–C bonds. Alternative methods using pseudohalides, such as triflates or nonaflates, are also suitable for this transformation. These substrates offer the advantages of simple access from readily available phenols and possible use for chemodivergent sequential SM couplings using electronically differentiated leaving groups. However, the hydrolysis of triflates is a common side reaction under Suzuki coupling conditions especially if the substrates contain polar functional groups. Here we present a systematic study of the hydrolysis of aryl triflates, which allowed the identification of reaction conditions suitable for the sequential Suzuki-Miyaura coupling of substituted iodoaryl triflates with various substituted pyridine boronic acids. Protic solvents proved beneficial for the chemoselective coupling producing biaryl triflates. In a subsequent Suzuki coupling the synthesis of terayl-based alpha helix mimetics as potential protein-protein interaction inhibitors was achieved.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134793"},"PeriodicalIF":2.1,"publicationDate":"2025-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144470038","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
Hydrogen bonding induces a mechanistic change in nucleophilic aromatic substitution with amine nucleophiles and aryl fluorides 氢键引起亲核芳取代与胺亲核试剂和芳基氟化物的机理变化
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-20 DOI: 10.1016/j.tet.2025.134788
Laurel S. Swanson, Sophia A. Verkleeren, Ethan S. Prout, María J. Román-Vasquez, Amanda K. Turek
{"title":"Hydrogen bonding induces a mechanistic change in nucleophilic aromatic substitution with amine nucleophiles and aryl fluorides","authors":"Laurel S. Swanson,&nbsp;Sophia A. Verkleeren,&nbsp;Ethan S. Prout,&nbsp;María J. Román-Vasquez,&nbsp;Amanda K. Turek","doi":"10.1016/j.tet.2025.134788","DOIUrl":"10.1016/j.tet.2025.134788","url":null,"abstract":"<div><div>Nucleophilic aromatic substitution (S<sub>N</sub>Ar) reactions are known to proceed through both stepwise and concerted pathways, dictated largely by electrophile structure. In this paper, we show that the mechanism of S<sub>N</sub>Ar is influenced by intramolecular hydrogen bonding to the leaving group. We propose that this corresponds to a mechanistic transition from a stepwise/borderline mechanism to a concerted mechanism, as a result of stabilization of the elimination transition state. Our conclusions are supported by kinetic analysis examining the effects of the H-bond donor, the electrophile, and the nucleophile.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134788"},"PeriodicalIF":2.1,"publicationDate":"2025-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144489375","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
Rational development of dual-channel fluorescent probe for detecting SO2 and H2S without signal crosstalk in Chinese herbal medicines and living organisms 合理研制无信号串扰检测中草药和生物体内二氧化硫和硫化氢的双通道荧光探针
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-20 DOI: 10.1016/j.tet.2025.134794
Chao Gao, Dan-Dan Cheng, Yang Liu, Ming-Lan Ma, Hai-Rong Cui
{"title":"Rational development of dual-channel fluorescent probe for detecting SO2 and H2S without signal crosstalk in Chinese herbal medicines and living organisms","authors":"Chao Gao,&nbsp;Dan-Dan Cheng,&nbsp;Yang Liu,&nbsp;Ming-Lan Ma,&nbsp;Hai-Rong Cui","doi":"10.1016/j.tet.2025.134794","DOIUrl":"10.1016/j.tet.2025.134794","url":null,"abstract":"<div><div>The development of a bifunctional fluorescent probe for the simultaneous detection of SO<sub>2</sub> and H<sub>2</sub>S in Chinese herbal medicines and living organisms is vital for human health. In this study, we present a novel fluorescent probe, <strong>TTP</strong>, which exhibits a fluorescence turn-on response to both SO<sub>2</sub> and H<sub>2</sub>S through two independent fluorescent channels. Notably, this probe demonstrates a significant difference in response times for SO<sub>2</sub> (10 s) and H<sub>2</sub>S (60 s), and the fluorescence response to one substance remains unaffected by the presence of the other, thus effectively eliminating the problem of signal crosstalk during the simultaneous detection. Integrating with a smartphone sensing platform, probe <strong>TTP</strong> realizes the convenient, rapid, quantitative, and on-site detection of SO<sub>2</sub> and H<sub>2</sub>S in various Chinese herbal medicines. Additionally, <strong>TTP</strong> is suitable for the real-time monitoring of SO<sub>2</sub> and H<sub>2</sub>S levels in living cells and zebrafish.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134794"},"PeriodicalIF":2.1,"publicationDate":"2025-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144366347","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
Electrosynthesis of four-membered ring systems 四元环体系的电合成
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-19 DOI: 10.1016/j.tet.2025.134786
Thanh-Nhan Van Do
{"title":"Electrosynthesis of four-membered ring systems","authors":"Thanh-Nhan Van Do","doi":"10.1016/j.tet.2025.134786","DOIUrl":"10.1016/j.tet.2025.134786","url":null,"abstract":"<div><div>Four-membered ring compounds, such as cyclobutanes, oxetanes, azetidines, and thietanes, are important structural motifs in bioactive molecules (natural products, pharmaceuticals), materials, and as intermediates in organic synthesis. Their strained ring systems possess unique reactivity and physicochemical properties, making their synthesis a focal point in organic chemistry. While [2 + 2] photocycloaddition, driven by light or photocatalysts, is the most common method for constructing four-membered rings, electrochemical synthesis offers a promising, yet underexplored, alternative. This comprehensive review highlights the electrochemical synthesis of four-membered ring systems, emphasizing their mechanisms, advantages, and potential.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134786"},"PeriodicalIF":2.1,"publicationDate":"2025-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144523483","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
Synthesis of chiral bicyclic proline analogs 手性双环脯氨酸类似物的合成
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-18 DOI: 10.1016/j.tet.2025.134792
Radosław Gaida , Adam Włodarczyk , Marek Daszkiewicz , Elżbieta Wojaczyńska
{"title":"Synthesis of chiral bicyclic proline analogs","authors":"Radosław Gaida ,&nbsp;Adam Włodarczyk ,&nbsp;Marek Daszkiewicz ,&nbsp;Elżbieta Wojaczyńska","doi":"10.1016/j.tet.2025.134792","DOIUrl":"10.1016/j.tet.2025.134792","url":null,"abstract":"<div><div>A series of bicyclic proline analogs, carboxylic acids derived from 2-azabicyclo[2.2.1]heptane and 2-azabicyclo[2.2.2]octane were prepared, and five derivatives were characterized by X-ray crystallography, which allowed unambiguous configurational assignment of obtained stereoisomers. The possibility to use of these building blocks in the synthesis of peptides was tested.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134792"},"PeriodicalIF":2.1,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144330897","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
Multi-component reactions using selenium powder: Synthesis of 4,5-dihydro-1,3-selenazol-2-amine derivatives 用硒粉进行多组分反应：合成4,5-二氢-1,3-硒唑-2-胺衍生物
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-18 DOI: 10.1016/j.tet.2025.134790
Zhang Zhang , Guo-Hui Liu , Yu-Yang Xie, Li-Qiu Liu, Ying-Chun Wang
{"title":"Multi-component reactions using selenium powder: Synthesis of 4,5-dihydro-1,3-selenazol-2-amine derivatives","authors":"Zhang Zhang ,&nbsp;Guo-Hui Liu ,&nbsp;Yu-Yang Xie,&nbsp;Li-Qiu Liu,&nbsp;Ying-Chun Wang","doi":"10.1016/j.tet.2025.134790","DOIUrl":"10.1016/j.tet.2025.134790","url":null,"abstract":"<div><div>A method of synthesis of 4,5-dihydro-1,3-selenazole-2-amine derivatives with three components promoted by triethylamine was proposed. The method utilizes selenium powder as a safe, low-cost selenium source and isocyanides as nitrogen donors, achieving high yields under mild, straightforward conditions. This reaction constructs two C–Se bonds and one C–N bond in a single step, with excellent substrate scope and functional group tolerance. Its simplicity, high atom economy, and use of non-toxic, inexpensive materials make it a practical and sustainable strategy for synthesizing bioactive organoselenium compounds, overcoming limitations of traditional approaches.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134790"},"PeriodicalIF":2.1,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144470035","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
Direct C–H aminocarbonylation of quinone derivatives with isocyanides under transition-metal free conditions 醌类衍生物与异氰酸酯在无过渡金属条件下的直接C-H氨基羰基化反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-14 DOI: 10.1016/j.tet.2025.134779
Yingjie Zhang, Yuxuan Zhao, Jiankang Ou, Zeguo Fang, Qian Zhang, Dong Li
{"title":"Direct C–H aminocarbonylation of quinone derivatives with isocyanides under transition-metal free conditions","authors":"Yingjie Zhang,&nbsp;Yuxuan Zhao,&nbsp;Jiankang Ou,&nbsp;Zeguo Fang,&nbsp;Qian Zhang,&nbsp;Dong Li","doi":"10.1016/j.tet.2025.134779","DOIUrl":"10.1016/j.tet.2025.134779","url":null,"abstract":"<div><div>An efficient and facile C–H aminocarbonylation of quinone derivatives with isocyanides for the synthesis of corresponding amides was developed. This reaction was promoted by inorganic persulfate under transition-metal free conditions. A broad substrate scope including quinoxalines and quinoxalinones were exhibited by this method, affording the corresponding amides in moderated to good yields.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134779"},"PeriodicalIF":2.1,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144322057","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 iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7'-cyclopenta[d]pyrimidin]-4-one core 亲电性碘离子介导的4-（5-（芳基乙基）嘧啶-4-基）苯酚的螺旋环化反应生成螺旋[环己[2,5]二烯-1,7'-环五[d]嘧啶]-4- 1核
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-14 DOI: 10.1016/j.tet.2025.134791
Nikolai A. Arutiunov, Stanislav V. Shcherbakov, Daria A. Shtal, Maksim O. Shcheglov, Kirill V. Tolstov, Daria I. Murashkina, Nicolai A. Aksenov, Alexander V. Aksenov
{"title":"Electrophilic iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7'-cyclopenta[d]pyrimidin]-4-one core","authors":"Nikolai A. Arutiunov,&nbsp;Stanislav V. Shcherbakov,&nbsp;Daria A. Shtal,&nbsp;Maksim O. Shcheglov,&nbsp;Kirill V. Tolstov,&nbsp;Daria I. Murashkina,&nbsp;Nicolai A. Aksenov,&nbsp;Alexander V. Aksenov","doi":"10.1016/j.tet.2025.134791","DOIUrl":"10.1016/j.tet.2025.134791","url":null,"abstract":"<div><div>Novel iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols leading to spiro[cyclohexa[2,5]diene-1,7'-cyclopenta[<em>d</em>]pyrimidin]-4-one core was developed. This sequence, based commercially available reagents starts with acid-catalyzed electrophilic alkylation of phenols with 5-bromopyrimidine. Subsequently, an oxidation, palladium-catalyzed Sonogashira cross-coupling reaction and electrophilic spirocyclization, allowed to target product with good yields and simple synthetic protocols.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134791"},"PeriodicalIF":2.1,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144291435","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
Diastereodivergent synthesis of novel dispiro(imidazothiazolotriazine-pyrrolidin-oxindoles) based on ortho- and meta-nitrobenzylidene derivatives of imidazothiazolotriazine 基于咪唑噻唑三嗪邻硝基和间硝基苄基衍生物的新型咪唑噻唑三嗪-吡咯烷-氧吲哚的非对映发散合成
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-14 DOI: 10.1016/j.tet.2025.134782
Alexei N. Izmest'ev , Sergey S. Isakov , Yuri A. Strelenko , Angelina N. Kravchenko , Galina A. Gazieva
{"title":"Diastereodivergent synthesis of novel dispiro(imidazothiazolotriazine-pyrrolidin-oxindoles) based on ortho- and meta-nitrobenzylidene derivatives of imidazothiazolotriazine","authors":"Alexei N. Izmest'ev ,&nbsp;Sergey S. Isakov ,&nbsp;Yuri A. Strelenko ,&nbsp;Angelina N. Kravchenko ,&nbsp;Galina A. Gazieva","doi":"10.1016/j.tet.2025.134782","DOIUrl":"10.1016/j.tet.2025.134782","url":null,"abstract":"<div><div>Four series of dispiro-fused polyheterocyclic compounds containing spiro(pyrrolidine-2,3′-oxindole) and imidazothiazolotriazine moieties were prepared by [3 + 2] cycloaddition of azomethine ylide to <em>ortho</em>- and <em>meta</em>-nitrobenzylidene derivatives of imidazothiazolotriazine. It was shown that ylide cycloaddition occurs to both diastereotopic faces of the dipolarophiles to give the target compounds as two diastereomers. Skeletal rearrangement of the major dispiro(imidazo[4,5-<em>e</em>]thiazolo[3,2-<em>b</em>][1,2,4]triazine-6,3′-pyrrolidin-2′,3″-oxindoles) (<em>anti</em>-<em>exo</em>-diastereomers) gave isomeric dispiro(imidazo[4,5-<em>e</em>]thiazolo[2,3-<em>c</em>][1,2,4]triazine-7,3′-pyrrolidin-2′,3″-oxindoles) (angular <em>syn</em>-<em>exo</em>-diastereomers) that are inaccessible by the direct [3 + 2] cycloaddition reaction.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134782"},"PeriodicalIF":2.1,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144298100","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
Sustainable synthesis of cannabinoids via metal-free aromatic deformylation 通过无金属芳族脱甲酰化可持续合成大麻素
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-13 DOI: 10.1016/j.tet.2025.134789
Gil Dinnar , Oriyan Cohen , Prakash Jagtap , Sanaa Musa
{"title":"Sustainable synthesis of cannabinoids via metal-free aromatic deformylation","authors":"Gil Dinnar ,&nbsp;Oriyan Cohen ,&nbsp;Prakash Jagtap ,&nbsp;Sanaa Musa","doi":"10.1016/j.tet.2025.134789","DOIUrl":"10.1016/j.tet.2025.134789","url":null,"abstract":"<div><div>Cannabinoids, the bioactive compounds of the <em>Cannabis</em> genus, have gained considerable attention for their potential therapeutic applications variety of health conditions. Cannabidiol, in particular, has been studied for its diverse pharmacological properties, including antioxidant, anticancer, anti-inflammatory, and neuroprotective effects. To enhance the accessibility and efficacy of cannabinoids, synthetic approaches have been explored, focusing on improving yields and reducing the creation of unwanted byproducts. This study introduces a novel metal-free deformylation method for synthesizing cannabinoid derivatives from their corresponding cannabinoid aldehyde. We have developed optimized reaction conditions that utilize trimethyl orthoformate as a methanol donor in combination with <em>p</em>-toluenesulfonic acid, which enables high-yield conversion of 3-formyl-cannabinoid to cannabinoid with minimal formation of byproducts. Furthermore, we successfully applied this methodology to a range of other cannabinoid aldehydes, producing cannabinoids with varying alkyl chain lengths. The reaction pathway revealed a nucleophilic substitution mechanism that facilitates the removal of the aldehyde group and promotes efficient cannabinoid synthesis. This metal-free approach offers a sustainable alternative to traditional catalytic methods, which could be really valuable for advancing cannabinoid research and pharmaceutical development.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134789"},"PeriodicalIF":2.1,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144291434","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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