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Co-catalyzed sp3-sp3 coupling enabled by hydrofunctionalization of alkenes with nucleophiles 通过烯烃与亲核试剂的加氢官能化，共催化sp3-sp3偶联
Tetrahedron chem Pub Date : 2025-06-20 DOI: 10.1016/j.tchem.2025.100142
Li-Xia Liu , Muneer-ul-Shafi Bhat , Yu-Long Li , Wei Shu
{"title":"Co-catalyzed sp3-sp3 coupling enabled by hydrofunctionalization of alkenes with nucleophiles","authors":"Li-Xia Liu ,&nbsp;Muneer-ul-Shafi Bhat ,&nbsp;Yu-Long Li ,&nbsp;Wei Shu","doi":"10.1016/j.tchem.2025.100142","DOIUrl":"10.1016/j.tchem.2025.100142","url":null,"abstract":"<div><div>Complementary to classical transition-metal-catalyzed cross-coupling reactions, transition-metal-catalyzed hydrofunctionalization of alkenes has emerged as a powerful strategy for direct and rapid construction of <em>sp</em><sup>3</sup>-<em>sp</em><sup>3</sup> linkages. Among various metals, cobalt has been widely used as a catalyst in the hydrofunctionalization of alkenes, demonstrating versatile catalytic reactivity for both electrophiles and nucleophiles to forge <em>sp</em><sup>3</sup>-<em>sp</em><sup>3</sup> bonds. When employing nucleophiles as coupling partners, the hydrofunctionalization reactions usually requires the addition of oxidants, due to the presence of nucleophilic intermediate generated through cobalt-hydride-mediated hydrogen atom transfer (HAT) with alkenes. Cobalt-catalyzed hydrofunctionalizations of alkenes with nucleophiles represent an interesting and emerging strategy due to the use of both reductant and oxidant. This review summarizes the recent development of Co-catalyzed hydrofunctionalization of alkenes with nucleophiles, focusing on the construction of various C(<em>sp</em><sup>3</sup>)-X(<em>sp</em><sup>3</sup>) bonds (X = N, O, S, F). Future direction of this strategy to broaden the scope of <em>sp</em><sup>3</sup>-<em>sp</em><sup>3</sup> bond formation is also discussed.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"15 ","pages":"Article 100142"},"PeriodicalIF":0.0,"publicationDate":"2025-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144366901","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
Construction of C–S bond via reductive cross-coupling 还原交叉偶联法构建C-S键
Tetrahedron chem Pub Date : 2025-06-18 DOI: 10.1016/j.tchem.2025.100141
Muhammad Bilal, Xiao-Bo Liu, Yu-Feng Liang
{"title":"Construction of C–S bond via reductive cross-coupling","authors":"Muhammad Bilal,&nbsp;Xiao-Bo Liu,&nbsp;Yu-Feng Liang","doi":"10.1016/j.tchem.2025.100141","DOIUrl":"10.1016/j.tchem.2025.100141","url":null,"abstract":"<div><div>Sulfur-containing compounds have attracted considerable interest due to their varied applications in natural products, agriculture, pharmaceuticals, and organic materials. The development of rapid and efficient synthesis and transformation methods for these compounds is essential. The reductive coupling of electrophiles has emerged as a potent strategy for constructing sulfur-based molecules. While significant advancements have been achieved in cross-coupling reactions involving organic pseudohalides and halides, there is an increasing focus on reactions with more accessible, cost-effective, stable, yet less reactive electrophiles. This review majorly emphasizes the integration of cheap metals including nickel, cobalt iron and copper, electrochemical or photochemical reactions, and catalyst-free reductive cross-coupling techniques for the preparation of thioethers, disulfides, sulfones, and thioesters. It also examines the mechanistic insights underlying these strategies, thereby enhancing our comprehension of their potential for a broad spectrum of synthetic applications.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"15 ","pages":"Article 100141"},"PeriodicalIF":0.0,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144321190","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 organic synthesis 采访2025年有机合成四面体青年研究者奖
Tetrahedron chem Pub Date : 2025-06-13 DOI: 10.1016/j.tchem.2025.100140
Song Lin, Wing Ho So, Jun Kee Cheng
{"title":"Interview with the 2025 Tetrahedron young investigator award for organic synthesis","authors":"Song Lin,&nbsp;Wing Ho So,&nbsp;Jun Kee Cheng","doi":"10.1016/j.tchem.2025.100140","DOIUrl":"10.1016/j.tchem.2025.100140","url":null,"abstract":"","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"15 ","pages":"Article 100140"},"PeriodicalIF":0.0,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144517716","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
Rapid access to phenanthrene-based fused lactones via C(sp3)–H bond functionalization initiated triple ring construction 通过C(sp3) -氢键功能化快速获得基于菲的熔融内酯，引发了三环结构
Tetrahedron chem Pub Date : 2025-06-10 DOI: 10.1016/j.tchem.2025.100138
Ryosei Koyama , Takayuki Matsuno , Masahiro Anada , Shunsuke Sueki , Kosho Makino , Tomoko Kawasaki-Takasuka , Keiji Mori
{"title":"Rapid access to phenanthrene-based fused lactones via C(sp3)–H bond functionalization initiated triple ring construction","authors":"Ryosei Koyama ,&nbsp;Takayuki Matsuno ,&nbsp;Masahiro Anada ,&nbsp;Shunsuke Sueki ,&nbsp;Kosho Makino ,&nbsp;Tomoko Kawasaki-Takasuka ,&nbsp;Keiji Mori","doi":"10.1016/j.tchem.2025.100138","DOIUrl":"10.1016/j.tchem.2025.100138","url":null,"abstract":"<div><div>We report the formation of phenanthrene-based fused lactone derivatives based on C(sp<sup>3</sup>)–H bond functionalization initiated triple ring construction. Employing a stoichiometric amount of Bi(OTf)<sub>3</sub> was the key to the success of the present reaction. The reaction was stopped in the double ring construction under catalytic conditions. A detailed examination suggested that selecting an alkyl group adjacent to a methoxy group was critical to achieving the third cyclization (lactonization).</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"15 ","pages":"Article 100138"},"PeriodicalIF":0.0,"publicationDate":"2025-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144263172","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
Recent advances in asymmetric [2+1] cycloaddition with α-cyano diazo compounds [2+1]不对称环加成与α-氰基重氮化合物的研究进展
Tetrahedron chem Pub Date : 2025-06-07 DOI: 10.1016/j.tchem.2025.100137
Shuicai Chen , Qiuzhan Huang , Xiaoyu Ren , Zhen Guo , Chengming Wang , Cong-Ying Zhou
{"title":"Recent advances in asymmetric [2+1] cycloaddition with α-cyano diazo compounds","authors":"Shuicai Chen ,&nbsp;Qiuzhan Huang ,&nbsp;Xiaoyu Ren ,&nbsp;Zhen Guo ,&nbsp;Chengming Wang ,&nbsp;Cong-Ying Zhou","doi":"10.1016/j.tchem.2025.100137","DOIUrl":"10.1016/j.tchem.2025.100137","url":null,"abstract":"<div><div>The asymmetric [2 + 1] cycloaddition of α-cyano diazo compounds has emerged as an efficient and versatile strategy for synthesizing cyano-substituted cyclopropanes, which are valuable scaffolds in medicinal chemistry, materials science, and natural product synthesis. The unique electrophilicity and planar conjugation of cyano-substituted carbenes have enabled highly selective [2 + 1] cycloaddition reactions with a wide range of substrates, including alkenes, alkynes, allenes, and aromatic compounds. Recent advancements in catalyst design, particularly the use of dirhodium(II) complexes, cobalt(II) porphyrins, and biocatalysts like engineered myoglobin, have achieved remarkable levels of enantioselectivity and diastereoselectivity. These methodologies have not only expanded the synthetic scope but also revealed mechanistic insights into carbene transfer reactions, such as the influence of π–π stacking and hydrogen bonding on stereoselectivity. Despite these successes, challenges remain in addressing substrate limitations, enhancing reaction efficiency under mild and sustainable conditions, and exploring new applications in drug discovery and beyond. This review highlights the latest developments in this field, providing a foundation for future research into the design of novel catalytic systems and the broader utilization of α-cyano diazo compounds in synthetic organic chemistry.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"15 ","pages":"Article 100137"},"PeriodicalIF":0.0,"publicationDate":"2025-06-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144288970","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
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
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