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Nickel photocatalytic aryl halide and amine C–N bond coupling 镍光催化芳基卤化物与胺C-N键偶联
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-05-01 Epub Date: 2025-12-25 DOI: 10.1016/j.tet.2025.135107
Sazia Sultana, Ryan Eleveld, Md Matiar Rahman, Aaron L. Odom
{"title":"Nickel photocatalytic aryl halide and amine C–N bond coupling","authors":"Sazia Sultana,&nbsp;Ryan Eleveld,&nbsp;Md Matiar Rahman,&nbsp;Aaron L. Odom","doi":"10.1016/j.tet.2025.135107","DOIUrl":"10.1016/j.tet.2025.135107","url":null,"abstract":"<div><div>Aryl bromides and iodides can be coupled with primary and secondary amines using NiBr<sub>2</sub> and DABCO in DMA or DMSO with 427 nm light, without the use of palladium, expensive phosphines, or photoredox catalysts. The reactions are very sensitive to the solvent used, with some reactions working in DMA and others in DMSO for reasons that are currently unknown. An NRF2 inhibitor, ZH-71, was prepared using the method, which required a mixture of DMA and DMSO for the reaction to proceed. The reactions can be optimized to excellent yields and work with a large range of substrates.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"193 ","pages":"Article 135107"},"PeriodicalIF":2.2,"publicationDate":"2026-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145872721","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
Phosphorus-based redox organocatalysis for sustainable synthesis: A literature review 基于磷的氧化还原有机催化可持续合成：文献综述
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-05-01 Epub Date: 2025-12-26 DOI: 10.1016/j.tet.2025.135124
Raphaël El Bekri-Saudain , Pierre-Olivier Butin , Lucas Mele , Louise Fourbet, Louise Musikas, David Virieux, Tahar Ayad
{"title":"Phosphorus-based redox organocatalysis for sustainable synthesis: A literature review","authors":"Raphaël El Bekri-Saudain ,&nbsp;Pierre-Olivier Butin ,&nbsp;Lucas Mele ,&nbsp;Louise Fourbet,&nbsp;Louise Musikas,&nbsp;David Virieux,&nbsp;Tahar Ayad","doi":"10.1016/j.tet.2025.135124","DOIUrl":"10.1016/j.tet.2025.135124","url":null,"abstract":"<div><div>Fundamental transformations in organic synthesis, such as the Wittig, Staudinger, Appel and Mitsunobu reactions, have traditionally relied on stoichiometric amounts of phosphine, leading to phosphine oxide by-products. Due to their high stability and polarity, these oxides complicate purification processes and diminish overall reaction efficiency. In 2015, members of the American Chemical Society emphasized the need to develop methodologies that minimize or eliminate phosphine oxide waste. This call to action has since spurred widespread innovation and driven numerous research groups to reassess their synthetic approaches. This review highlights recent advances over the past two decades in phosphorus-based redox organocatalysis, which represent a promising direction for expanding the scope and sustainability of phosphorus-mediated transformations.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"193 ","pages":"Article 135124"},"PeriodicalIF":2.2,"publicationDate":"2026-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145872719","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
Tandem/domino reactions in glycoscience to access diverse glycohybrids: Recent developments and future perspective 糖科学中的串联/多米诺反应获取多种糖杂化物：最新进展和未来展望
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-05-01 Epub Date: 2025-12-31 DOI: 10.1016/j.tet.2025.135129
Danish Ansari , Mangal S. Yadav , Anindra Sharma , Sanchayita Rajkhowa , Shristy Maurya , Supriya Singh , Vinod K. Tiwari
{"title":"Tandem/domino reactions in glycoscience to access diverse glycohybrids: Recent developments and future perspective","authors":"Danish Ansari ,&nbsp;Mangal S. Yadav ,&nbsp;Anindra Sharma ,&nbsp;Sanchayita Rajkhowa ,&nbsp;Shristy Maurya ,&nbsp;Supriya Singh ,&nbsp;Vinod K. Tiwari","doi":"10.1016/j.tet.2025.135129","DOIUrl":"10.1016/j.tet.2025.135129","url":null,"abstract":"<div><div>Carbohydrates, due to their inherent chirality, high functional group density, and structural diversity, have emerged as powerful scaffolds in MCR-tandem synthesis of biologically relevant molecules. These naturally occurring polyhydroxy compounds offer a versatile platform for the rapid generation of complex molecular architectures with high stereochemical fidelity. In MCR tandem reactions, carbohydrate-derived molecular scaffolds may facilitate efficient bond-forming sequences by enabling multiple transformations in a single synthetic operation, often under mild reaction conditions. The role of sugar-based scaffolds further extends from passive frameworks to active participants in reaction mechanisms that eventually influence their regio- and stereoselectivity to demonstrate the utilities in synthesizing biologically active molecules, natural product mimetic, and glycomimetics. This review discusses the emerging aspects of Domino approach to enhance the synthetic efficiency and atom economy, aligning with the principles of green chemistry that make such carbohydrate-based tandem strategies increasingly attractive in organic synthesis along with future perspectives.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"193 ","pages":"Article 135129"},"PeriodicalIF":2.2,"publicationDate":"2026-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145882868","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
Pyromellitic diimide-derived quaternary ammonium salts: Synthesis and application as efficient copper electroplating levelers 焦二酰二亚胺衍生季铵盐：作为高效镀铜矫平剂的合成及应用
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-19 DOI: 10.1016/j.tet.2025.135095
Fengyan Lu , Xuyang Li , Qi Zhu , Lifeng Chu , Jianwei Han , Limin Wang
{"title":"Pyromellitic diimide-derived quaternary ammonium salts: Synthesis and application as efficient copper electroplating levelers","authors":"Fengyan Lu ,&nbsp;Xuyang Li ,&nbsp;Qi Zhu ,&nbsp;Lifeng Chu ,&nbsp;Jianwei Han ,&nbsp;Limin Wang","doi":"10.1016/j.tet.2025.135095","DOIUrl":"10.1016/j.tet.2025.135095","url":null,"abstract":"<div><div>The high performance copper electrodeposition in high-aspect-ratio through-holes for printed circuit board (PCB) is a challenge in the electronics industry. In this text, a family of pyromellitic diimide (PMD) derived quaternary ammonium salts were synthesized in good yields, which exhibited strong suppression of copper deposition. Among these, PMD-bipyridinium (Bpy) salt demonstrates the most pronounced effect, showing excellent adsorption behavior on copper surfaces, as confirmed by electrochemical analyses, theoretical calculations, and molecular dynamics simulations. Practical plating evaluations further verified the superior filling and leveling performance of the PMD-Bpy salt, achieving uniform and defect-free copper electrodeposition.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135095"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145838240","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 novel naphthopyran dyes and their photochromic properties in resin lenses 新型萘吡喃染料的合成及其在树脂透镜中的光致变色性能
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-24 DOI: 10.1016/j.tet.2025.135126
Qin Li , Shanglin Li , Zhouyang Long , Minyi Liang , Zihao Yin , Pingbo Zhang , Yan Leng
{"title":"Synthesis of novel naphthopyran dyes and their photochromic properties in resin lenses","authors":"Qin Li ,&nbsp;Shanglin Li ,&nbsp;Zhouyang Long ,&nbsp;Minyi Liang ,&nbsp;Zihao Yin ,&nbsp;Pingbo Zhang ,&nbsp;Yan Leng","doi":"10.1016/j.tet.2025.135126","DOIUrl":"10.1016/j.tet.2025.135126","url":null,"abstract":"<div><div>Naphthopyran compounds represent a significant category of photochromic molecules that can reversibly change color when exposed to UV light and have been extensively utilized in ophthalmic lenses. However, the slow adaptation from a colored state to a colorless state in the absence of UV light is one of the limitations. Herein, we have designed and synthesized a series of naphthopyran dyes with varying substituent modifications. Our findings indicate that expanding the conjugated structure of naphthopyran and introducing a –OH group at the indeno bridge can effectively adjust the visible spectrum of the dye and increase the photosensitivity of the ring-opening and ring-closing reaction. This leads to the production of more vivid green hues and facilitates a swift transition between the colorless and colored states. The clear photochromic-photovoltaic structure-property relationships for these naphthopyran dyes are established by DFT calculation, and they are shown to demonstrate sensitive photochromic responses in resin lenses.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135126"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145838239","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
Transition-metal-catalyzed/mediated direct C(sp2)–H selenylation of heterocycles 过渡金属催化/介导的杂环直接C(sp2) -H硒化反应
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-17 DOI: 10.1016/j.tet.2025.135106
Shi-Jiao Zhang , Yu Teng , Hong-Shuang Li
{"title":"Transition-metal-catalyzed/mediated direct C(sp2)–H selenylation of heterocycles","authors":"Shi-Jiao Zhang ,&nbsp;Yu Teng ,&nbsp;Hong-Shuang Li","doi":"10.1016/j.tet.2025.135106","DOIUrl":"10.1016/j.tet.2025.135106","url":null,"abstract":"<div><div>Small-molecule heterocycles play a critical role in FDA-approved drugs. Remarkably, the introduction of selenium motifs into heterocyclic compounds imparts unique physicochemical properties and enhanced pharmacological activities. Direct C(sp<sup>2</sup>)–H selenylation of heterocycles represents one of the most atom-economical and effective approaches for accessing heterocyclic selenides. Herein, we review recent advances in transition-metal-catalyzed or mediated C(sp<sup>2</sup>)–H selenylation of heteroaromatic compounds and uracils over the past five years. Specifically, we highlight representative selenylation examples, including substrate scope and limitations, along with comprehensive mechanistic interpretations. This review will help facilitate the development of chalcogenation of heterocycles and inspire further application of selenylated heterocyclic compounds in pharmaceutical chemistry.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135106"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145789478","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 pyrazolone functionalization: A review since 2020 吡唑酮功能化研究进展：2020年以来综述
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-17 DOI: 10.1016/j.tet.2025.135103
Mao-Lin Liao , Peng-Peng Liu , Chang-Liang Tan , Ping-Gui Li , Liang-Hua Zou
{"title":"Advances in pyrazolone functionalization: A review since 2020","authors":"Mao-Lin Liao ,&nbsp;Peng-Peng Liu ,&nbsp;Chang-Liang Tan ,&nbsp;Ping-Gui Li ,&nbsp;Liang-Hua Zou","doi":"10.1016/j.tet.2025.135103","DOIUrl":"10.1016/j.tet.2025.135103","url":null,"abstract":"<div><div>Pyrazolones are a class of nitrogen-containing heterocyclic compounds of great value in the fields of synthetic chemistry and medicinal chemistry. This review comprehensively summarizes the iconic research progress of pyrazolone functionalization reactions since 2020, including monosubstitution at the 4-position, 3,4,6-position annulation for constructing fused ring systems, 4-position disubstitution for spirocycle construction, and heterocycle construction involving the N–N bond. Through the use of novel catalysts, unique reaction conditions, and innovative reaction pathways, these reactions exhibit high selectivity, good substrate adaptability, and excellent atom economy. These advancements not only enrich the synthetic methods of pyrazolone derivatives but also provide important references for the development of novel bioactive molecules and functional materials, strongly promoting the development of related fields such as organic synthesis and drug research and development.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135103"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145838233","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 decarbonylative alkynylation of hydroxyquinoline carboxylic acid using dual C–H/C–O bond activation 钯催化羟基喹啉羧酸的脱羰烷基化反应
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-26 DOI: 10.1016/j.tet.2025.135127
Zebabanu Khalifa, Amit B. Patel
{"title":"Palladium-catalyzed decarbonylative alkynylation of hydroxyquinoline carboxylic acid using dual C–H/C–O bond activation","authors":"Zebabanu Khalifa,&nbsp;Amit B. Patel","doi":"10.1016/j.tet.2025.135127","DOIUrl":"10.1016/j.tet.2025.135127","url":null,"abstract":"<div><div>A versatile, atom-efficient, and sustainable decarbonylative Sonogashira cross-coupling approach has been disclosed by optimizing a range of palladium catalytic systems for enabling the direct construction of a C(sp<sup>2</sup>)-C(sp) bond between 4-hydroxyquinoline-3-carboxylic acid derivatives and structurally diverse terminal alkynes <em>via</em> dual C–O/C–H functionalization. This facile protocol has offered significant economic value due to its <em>in situ</em> functionality and well-tolerable substrate scopes, which provide reasonable yields up to 88 % with minimal byproduct generation. Also, mechanistic investigation revealed the efficiency of the palladium-ligand active species, which evolved valuable insights for the decarbonylative C(sp<sup>2</sup>)-C(sp) cross-coupling pathway within a single catalytic system. Hence, this present study introduces an operatively reliable and sustainable route for the late-stage functionalization of <em>N</em>-heteroaromatic scaffolds, offering significant potential for material synthesis, molecular diversification, and chemotherapeutic innovations by involving palladium-catalyzed decarbonylative Sonogashira cross-coupling.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135127"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145838232","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
Diels-Alder reaction: A versatile synthetic tool for the synthesis of terpenoids and alkaloids: A review Diels-Alder反应：一种合成萜类和生物碱的通用合成工具
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-17 DOI: 10.1016/j.tet.2025.135101
Muhammad Ikram , Asim Mansha , Samreen Gul Khan , Ameer Fawad Zahoor , Muhammad Naveed Anjum , Kulsoom Ghulam Ali , Freeha Hafeez , Aijaz Rasool Chaudhry , Ahmad Irfan , Muhammad Abbas
{"title":"Diels-Alder reaction: A versatile synthetic tool for the synthesis of terpenoids and alkaloids: A review","authors":"Muhammad Ikram ,&nbsp;Asim Mansha ,&nbsp;Samreen Gul Khan ,&nbsp;Ameer Fawad Zahoor ,&nbsp;Muhammad Naveed Anjum ,&nbsp;Kulsoom Ghulam Ali ,&nbsp;Freeha Hafeez ,&nbsp;Aijaz Rasool Chaudhry ,&nbsp;Ahmad Irfan ,&nbsp;Muhammad Abbas","doi":"10.1016/j.tet.2025.135101","DOIUrl":"10.1016/j.tet.2025.135101","url":null,"abstract":"<div><div>Diels-Alder reaction is a powerful transformation in organic synthesis due to its great potency to generate 6-membered ring system with multiple stereogenic centers in a concerted manner. This pericyclic reaction has been utilized for the construction of numerous complex scaffolds with highly intricate patterns. Herein, this widely studied topic in chemistry has been discussed in detail with its recent applications towards terpenoids and alkaloids, reported since 2020. Different modifications in Diels-Alder substrates, Lewis acids and organo-metallic catalysts further expand the utility of this reaction. The effect of substitution pattern on Diels-Alder substrates and other structural motifs has also been highlighted in this review which shows significant influence of the stereo- and regio-chemistry of Diels-Alder reaction in chasing the target molecule.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135101"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145881436","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
Gram-scale reduction of esters to alcohols using AlCl3/NaBH4 revisited: Solvent effect, scope, and limitations 用AlCl3/NaBH4还原克级酯为醇：溶剂效应、范围和限制
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-15 DOI: 10.1016/j.tet.2025.135102
Hai-yang Chen , Eman Fayad , Dalal Nasser Binjawhar , Hua-Li Qin
{"title":"Gram-scale reduction of esters to alcohols using AlCl3/NaBH4 revisited: Solvent effect, scope, and limitations","authors":"Hai-yang Chen ,&nbsp;Eman Fayad ,&nbsp;Dalal Nasser Binjawhar ,&nbsp;Hua-Li Qin","doi":"10.1016/j.tet.2025.135102","DOIUrl":"10.1016/j.tet.2025.135102","url":null,"abstract":"<div><div>Herein, we revisit the reduction of esters to primary alcohols using sodium borohydride and aluminum chloride. Solvent selection proved critical. An improved, more convenient procedure has been developed by replacing conventional diglyme with DME (1,2-dimethoxyethane). Mild reaction conditions, good functional group compatibility, gram-scale reaction, and operational simplicity demonstrate the power of this protocol.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135102"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145765750","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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