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Recent advances in haloarene synthesis by aryne reactions 炔反应合成卤代芳烃的研究进展
Tetrahedron chem Pub Date : 2025-06-01 DOI: 10.1016/j.tchem.2025.100136
Shinya Tabata, Suguru Yoshida
{"title":"Recent advances in haloarene synthesis by aryne reactions","authors":"Shinya Tabata,&nbsp;Suguru Yoshida","doi":"10.1016/j.tchem.2025.100136","DOIUrl":"10.1016/j.tchem.2025.100136","url":null,"abstract":"<div><div>Recent advances in haloarene synthesis by diverse transformations of aryne intermediates are summarized in this review. Regioselective reactions of 3-haloaryne intermediates have enabled the efficient synthesis of a wide variety of haloarenes, facilitated by structural distortion induced by the electron-withdrawing nature of halogen substituents. In addition, numerous halogenation-based transformations of aryne intermediates have been developed for the construction of highly functionalized haloarenes. These innovative aryne-based strategies offer access to structurally unique aromatic compounds, highlighting the pivotal role of halogens in modern synthetic chemistry. As a result, emerging synthetic methods involving aryne intermediates have proven valuable in various research fields, including materials chemistry and pharmaceutical sciences.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100136"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144231847","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
Interview with the 2025 Tetrahedron Young Investigator Award for Bioorganic and Medicinal Chemistry 采访2025年生物有机和药物化学四面体青年研究者奖
Tetrahedron chem Pub Date : 2025-05-27 DOI: 10.1016/j.tchem.2025.100135
Bryan C. Dickinson, Wing Ho So, Jun Kee Cheng
{"title":"Interview with the 2025 Tetrahedron Young Investigator Award for Bioorganic and Medicinal Chemistry","authors":"Bryan C. Dickinson,&nbsp;Wing Ho So,&nbsp;Jun Kee Cheng","doi":"10.1016/j.tchem.2025.100135","DOIUrl":"10.1016/j.tchem.2025.100135","url":null,"abstract":"","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"15 ","pages":"Article 100135"},"PeriodicalIF":0.0,"publicationDate":"2025-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144321184","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
Catalytic asymmetric desymmetrization of diesters: advances and perspectives 二酯催化不对称脱对称：进展与展望
Tetrahedron chem Pub Date : 2025-05-14 DOI: 10.1016/j.tchem.2025.100134
Yu Huang, Jia-Yu Liao
{"title":"Catalytic asymmetric desymmetrization of diesters: advances and perspectives","authors":"Yu Huang,&nbsp;Jia-Yu Liao","doi":"10.1016/j.tchem.2025.100134","DOIUrl":"10.1016/j.tchem.2025.100134","url":null,"abstract":"<div><div>Catalytic asymmetric desymmetrization of prochiral and <em>meso</em>-diesters has emerged as a powerful strategy for the synthesis of chiral compounds featuring tertiary or quaternary stereogenic carbon centers. This mini-review summarizes the recent progress in this rapidly growing field. The reported fruitful examples have been organized and presented according to their reaction types. In the end, a perspective on the current limitations and future opportunities is provided to inspire further developments in this area.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100134"},"PeriodicalIF":0.0,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144068276","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
Organocatalyzed asymmetric [2+2] cycloaddition of saccharin-derived endocyclic ketimines and allenoates for the synthesis of fused azetidines
Tetrahedron chem Pub Date : 2025-05-10 DOI: 10.1016/j.tchem.2025.100133
Xinyu Liu , Yunfeng Zhang , Luning Zhou , Dehai Li , De Wang
{"title":"Organocatalyzed asymmetric [2+2] cycloaddition of saccharin-derived endocyclic ketimines and allenoates for the synthesis of fused azetidines","authors":"Xinyu Liu ,&nbsp;Yunfeng Zhang ,&nbsp;Luning Zhou ,&nbsp;Dehai Li ,&nbsp;De Wang","doi":"10.1016/j.tchem.2025.100133","DOIUrl":"10.1016/j.tchem.2025.100133","url":null,"abstract":"<div><div>We report a novel enantioselective [2 + 2] cycloaddition of allenoate and endocyclic ketimine derived from saccharin, catalyzed by a chiral tertiary amine. The methodology enables the synthesis of fused tricyclic azetidines with a quaternary stereogenic center, exhibiting high enantioselectivity and efficiency. The broad range of substrates demonstrate the generality of the protocol, and the resulting functional products can be easily converted into a variety of valuable synthons such as thiazepine derivatives.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100133"},"PeriodicalIF":0.0,"publicationDate":"2025-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143943551","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
Synthetic nanographenes for cancer therapy 用于癌症治疗的合成纳米石墨烯
Tetrahedron chem Pub Date : 2025-04-22 DOI: 10.1016/j.tchem.2025.100132
Ranran Li, Chong-dao Lu, Peng An
{"title":"Synthetic nanographenes for cancer therapy","authors":"Ranran Li,&nbsp;Chong-dao Lu,&nbsp;Peng An","doi":"10.1016/j.tchem.2025.100132","DOIUrl":"10.1016/j.tchem.2025.100132","url":null,"abstract":"<div><div>Noninvasive cancer therapy, such as photodynamic therapy (PDT), photothermal therapy (PTT), and sonodynamic therapy (SDT) is becoming a promising option for cancer therapy. Being the most important factor, photosensitizer/sonosensitizer plays a pivotal role in the PDT, PTT, or SDT. Nanographenes (NGs), the large polycyclic aromatic hydrocarbons with nanoscale graphene structures, have received great attention. The significant efforts have been made by bottom-up synthesis strategy to prepare nanographenes with diverse structures and tunable properties. Notably, recent reports have suggested the NGs exhibit great potential as sensitizers for cancer therapy, which open up an avenue for the applications of NGs. In this review, we summarized these results by highlighting the synthesis of NG sensitizers and their efficiency in cancer therapy.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100132"},"PeriodicalIF":0.0,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143864651","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
Fujiwara-Moritani reaction: challenges and new opportunities 藤原-森谷反应：挑战与新机遇
Tetrahedron chem Pub Date : 2025-04-18 DOI: 10.1016/j.tchem.2025.100130
Xiaojian Chen , Jun Zhang , Yang Gao, Qian Chen, Yanping Huo, Xianwei Li
{"title":"Fujiwara-Moritani reaction: challenges and new opportunities","authors":"Xiaojian Chen ,&nbsp;Jun Zhang ,&nbsp;Yang Gao,&nbsp;Qian Chen,&nbsp;Yanping Huo,&nbsp;Xianwei Li","doi":"10.1016/j.tchem.2025.100130","DOIUrl":"10.1016/j.tchem.2025.100130","url":null,"abstract":"<div><div>Fujiwara-Moritani reaction has proven to be robust for the efficient construction of polyfunctionalized olefins and cyclic skeletons. Recent advances toward greener systems, compatibility with strongly coordinating heterocycle substrates and sterically hindered internal olefins, and achieving asymmetric catalysis have collectively opened new frontiers for Fujiwara-Moritani reaction.2009 Elsevier Ltd. All rights reserved.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100130"},"PeriodicalIF":0.0,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143860532","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
Photoinduced enantioselective transformations via o-quinodimethane intermediates 通过邻喹诺二甲烷中间体的光诱导对映选择性转化
Tetrahedron chem Pub Date : 2025-04-16 DOI: 10.1016/j.tchem.2025.100131
Liwen Xia , Qingqin Huang , Zhao-Fei Zhang , Lei Dai
{"title":"Photoinduced enantioselective transformations via o-quinodimethane intermediates","authors":"Liwen Xia ,&nbsp;Qingqin Huang ,&nbsp;Zhao-Fei Zhang ,&nbsp;Lei Dai","doi":"10.1016/j.tchem.2025.100131","DOIUrl":"10.1016/j.tchem.2025.100131","url":null,"abstract":"<div><div>The effective stereoselective control of transient intermediates remains a formidable challenge in synthetic chemistry. <em>o</em>-Quinodimethane generated by photo-irradation has been extensively investigated and widely utilized as a nucleophilic surrogate. Nevertheless, enantioselective transformations involving <em>o</em>-quinodimethane are still underdeveloped, due to the persistent challenges in intercepting these intermediates and achieving effective stereoselective control with chiral catalysts. In this review, we summarize recent advances in photoinduced enantioselective reactions of <em>o</em>-quinodimethane, highlighting catalytic strategies, mechanistic insights, and current limitations in the field.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100131"},"PeriodicalIF":0.0,"publicationDate":"2025-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143847937","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
Nickel-catalyzed synthesis of fluorine-bearing silane through halofluoroalkylation and hydrofluoroalkylation of alkenylsilanes 镍催化通过烯基硅烷的卤代氟烷基化和氢氟烷基化合成含氟硅烷
Tetrahedron chem Pub Date : 2025-04-14 DOI: 10.1016/j.tchem.2025.100129
Ting Su , Heng Wang , Wenxin Lu , Wei Huang , Qinglei Chong , Fanke Meng
{"title":"Nickel-catalyzed synthesis of fluorine-bearing silane through halofluoroalkylation and hydrofluoroalkylation of alkenylsilanes","authors":"Ting Su ,&nbsp;Heng Wang ,&nbsp;Wenxin Lu ,&nbsp;Wei Huang ,&nbsp;Qinglei Chong ,&nbsp;Fanke Meng","doi":"10.1016/j.tchem.2025.100129","DOIUrl":"10.1016/j.tchem.2025.100129","url":null,"abstract":"<div><div>Fluorine-bearing silanes have displayed widespread applications in organic synthesis and inorganic and material chemistry due to their high reactivity and versatility. However, the synthesis of fluorine-containing compounds featuring a difluorine-bearing silane is still underdeveloped. Here, we reported a simple, mild and efficient method for halofluoroalkylation and hydrofluoroalkylation of alkenylsilanes with bromodifluoroacetates under nickel catalysis, affording a variety of fluorine-bearing silanes in up to 89 % yield. This research was distinguished by its good functional group tolerance, moderate to good yields and exclusive regioselectivity.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100129"},"PeriodicalIF":0.0,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143843361","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
Radical SAM cyclophane synthase catalyzes uniform cyclophane formation at multiple Trp-motifs 自由基SAM环烷合成酶催化在多个trp基序上形成均匀的环烷
Tetrahedron chem Pub Date : 2025-03-27 DOI: 10.1016/j.tchem.2025.100128
Abujunaid Habib Khan , Jabal Rahmat Haedar , Anitra Zīle , Chin-Soon Phan
{"title":"Radical SAM cyclophane synthase catalyzes uniform cyclophane formation at multiple Trp-motifs","authors":"Abujunaid Habib Khan ,&nbsp;Jabal Rahmat Haedar ,&nbsp;Anitra Zīle ,&nbsp;Chin-Soon Phan","doi":"10.1016/j.tchem.2025.100128","DOIUrl":"10.1016/j.tchem.2025.100128","url":null,"abstract":"<div><div>Cyclophane-containing products from ribosomally synthesized and post-translationally modified peptides (RiPPs) are generated by radical SAM cyclophane synthases (rSAM). In the past few years, rSAM enzymes that catalyze uniform cyclophanes at multiple Trp-motifs on the precursor peptides have been discovered more frequently. These enzymes install C–C or C–O cross-links at the three-residue motifs between Trp-C5/C6/C7 and an <em>sp</em><sup>3</sup> carbon side chain to generate strained macrocycles. This mini-review will focus on the rSAM enzymes, WprB, OscB, XncB, FwwB and RscB to summarize the biosynthesis and NMR characterization of Trp-containing cyclophane products, and promiscuity of these enzymes.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100128"},"PeriodicalIF":0.0,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143738802","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
Total synthesis of the assigned structure of (+)-Maneolactenol （+）-马油酸醇配位结构的全合成
Tetrahedron chem Pub Date : 2025-03-13 DOI: 10.1016/j.tchem.2025.100127
Yidong Huang , Weiwu Ren
{"title":"Total synthesis of the assigned structure of (+)-Maneolactenol","authors":"Yidong Huang ,&nbsp;Weiwu Ren","doi":"10.1016/j.tchem.2025.100127","DOIUrl":"10.1016/j.tchem.2025.100127","url":null,"abstract":"<div><div>The first total synthesis of the assigned structure of (+)-maneolactenol, a marine natural product, has been completed in 7 steps. The pivotal transformations involve an asymmetric Diels-Alder reaction which serves as a key step in establishing stereochemistry, and the formation of core skeleton through iodolactonization. Particularly noteworthy are the selective reduction of acid to aldehyde and subsequent chelation-controlled stereoselective nucleophilic addition, facilitating the rapid and efficient assembly of side-chain motifs, as well as the selective reduction of the triple bond to <em>Z</em>-olefin moiety for the side chain construction. This strategy enabled the scalable synthesis of over 100 mg of the target compound, highlighting its practicality for larger-scale production.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100127"},"PeriodicalIF":0.0,"publicationDate":"2025-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143628787","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
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