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Three-component redox-neutral alkene difunctionalization by radical copper catalysis 自由基铜催化三组分氧化还原-中性烯烃双官能化
Tetrahedron chem Pub Date : 2025-09-01 Epub Date: 2025-08-27 DOI: 10.1016/j.tchem.2025.100144
Zhiming Feng , Jincai Zheng , Wei Zhou , Cong-Ying Zhou , Chengming Wang
{"title":"Three-component redox-neutral alkene difunctionalization by radical copper catalysis","authors":"Zhiming Feng ,&nbsp;Jincai Zheng ,&nbsp;Wei Zhou ,&nbsp;Cong-Ying Zhou ,&nbsp;Chengming Wang","doi":"10.1016/j.tchem.2025.100144","DOIUrl":"10.1016/j.tchem.2025.100144","url":null,"abstract":"<div><div>Three-component olefin difunctionalization represents a powerful strategy for constructing complex organic molecules. However, its advancement has been constrained by persistent challenges in chemoselectivity, environmental sustainability, and cost efficiency. The synergistic integration of cost-effective copper catalysis with radical chemistry offers a promising approach to address these limitations. This review provides a comprehensive analysis of copper-catalyzed, redox-neutral three-component olefin difunctionalization reactions, systematically examining both the diverse reaction types and their underlying mechanisms.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"15 ","pages":"Article 100144"},"PeriodicalIF":0.0,"publicationDate":"2025-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144912864","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 : 2025-09-01 Epub 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":"2025-09-01","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
Enantioselective Ni-catalyzed reductive cross-coupling of propargyl halides with vinyl halides to skipped enynes 镍催化异丙基卤化物与乙烯基卤化物的对映选择性交叉偶联反应
Tetrahedron chem Pub Date : 2025-09-01 Epub Date: 2025-08-28 DOI: 10.1016/j.tchem.2025.100145
Hang Zhou, Yuchi Zhao, Guangxia Wang, Zhonglin Tao
{"title":"Enantioselective Ni-catalyzed reductive cross-coupling of propargyl halides with vinyl halides to skipped enynes","authors":"Hang Zhou,&nbsp;Yuchi Zhao,&nbsp;Guangxia Wang,&nbsp;Zhonglin Tao","doi":"10.1016/j.tchem.2025.100145","DOIUrl":"10.1016/j.tchem.2025.100145","url":null,"abstract":"<div><div>Skipped enynes represent valuable structural motifs in synthetic chemistry due to their unique reactivity and prevalence in complex molecules. Herein, we describe a streamlined approach for the enantioselective synthesis of chiral skipped enynes via nickel-catalyzed asymmetric reductive cross-coupling between propargyl halides and vinyl halides. This transformation offers several notable advantages, including the use of readily available starting materials, mild reaction conditions, broad functional group tolerance, and potential for diverse downstream functionalizations.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"15 ","pages":"Article 100145"},"PeriodicalIF":0.0,"publicationDate":"2025-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144925652","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 : 2025-09-01 Epub 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":"2025-09-01","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
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 : 2025-09-01 Epub 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":"2025-09-01","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
Phosphorus fluoride exchange chemistry: An emerging strategy for covalent drug discovery 磷氟交换化学：共价药物发现的新策略
Tetrahedron chem Pub Date : 2025-09-01 Epub Date: 2025-08-22 DOI: 10.1016/j.tchem.2025.100143
Shuyue Yang , Yongkuan Li , Lingyun Yang, Bingchen Yu
{"title":"Phosphorus fluoride exchange chemistry: An emerging strategy for covalent drug discovery","authors":"Shuyue Yang ,&nbsp;Yongkuan Li ,&nbsp;Lingyun Yang,&nbsp;Bingchen Yu","doi":"10.1016/j.tchem.2025.100143","DOIUrl":"10.1016/j.tchem.2025.100143","url":null,"abstract":"<div><div>As a next-generation click chemistry platform, Phosphorus Fluoride Exchange (PFEx) involves the substitution of P(V)–F bonds with nucleophiles to form stable P(V)–O and P(V)–N linkages. Aryl phosphoramidofluoridates, key PFEx substrates, exhibit remarkable stability against hydrolysis and maintain integrity in complex biological environments. Despite this stability, they can react with nucleophilic amino acid residues such as lysine (Lys), histidine (His), tyrosine (Tyr), and cysteine (Cys) through proximity-enabled reactivity. Such features make PFEx chemistry a promising approach for designing novel covalent warheads. Similar to Sulfur (VI) Fluoride Exchange (SuFEx), PFEx is expected to have broad application in materials science, drug discovery, and chemical biology. In this perspective, we highlight PFEx as an emerging strategy for covalent warhead development. We begin by introducing the synthesis, stability, and reactivity of PFEx substrates. Next, we discuss proximity-enabled PFEx and its applications in creating covalent linkages with proteins under biocompatible conditions. Finally, we explore how PFEx can expand the current covalent warhead repertoire and outline key challenges and opportunities for its translation from bench to bedside.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"15 ","pages":"Article 100143"},"PeriodicalIF":0.0,"publicationDate":"2025-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144917124","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 : 2025-09-01 Epub 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":"2025-09-01","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
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 : 2025-09-01 Epub 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":"2025-09-01","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
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 : 2025-06-01 Epub 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":"2025-06-01","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
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 Epub Date: 2025-05-30 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
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