Pub Date : 2026-05-01Epub Date: 2025-12-25DOI: 10.1016/j.tet.2025.135107
Sazia Sultana, Ryan Eleveld, Md Matiar Rahman, Aaron L. Odom
Aryl bromides and iodides can be coupled with primary and secondary amines using NiBr2 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.
{"title":"Nickel photocatalytic aryl halide and amine C–N bond coupling","authors":"Sazia Sultana, Ryan Eleveld, Md Matiar Rahman, 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}
Pub Date : 2026-05-01Epub Date: 2025-12-26DOI: 10.1016/j.tet.2025.135124
Raphaël El Bekri-Saudain , Pierre-Olivier Butin , Lucas Mele , Louise Fourbet, Louise Musikas, David Virieux, Tahar Ayad
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.
有机合成中的基本转变，如Wittig、Staudinger、Appel和Mitsunobu反应，传统上依赖于化学计量量的磷化氢，从而产生氧化磷化氢的副产品。由于它们的高稳定性和极性，这些氧化物使纯化过程复杂化，降低了整体反应效率。2015年，美国化学会（American Chemical Society）的成员强调，有必要开发出减少或消除氧化膦废物的方法。这一行动呼吁激发了广泛的创新，并促使许多研究小组重新评估他们的综合方法。这篇综述强调了过去二十年来磷基氧化还原有机催化的最新进展，这代表了扩大磷介导转化的范围和可持续性的有希望的方向。
{"title":"Phosphorus-based redox organocatalysis for sustainable synthesis: A literature review","authors":"Raphaël El Bekri-Saudain , Pierre-Olivier Butin , Lucas Mele , Louise Fourbet, Louise Musikas, David Virieux, 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}
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.
{"title":"Tandem/domino reactions in glycoscience to access diverse glycohybrids: Recent developments and future perspective","authors":"Danish Ansari , Mangal S. Yadav , Anindra Sharma , Sanchayita Rajkhowa , Shristy Maurya , Supriya Singh , 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}
Pub Date : 2026-04-01Epub Date: 2025-12-19DOI: 10.1016/j.tet.2025.135095
Fengyan Lu , Xuyang Li , Qi Zhu , Lifeng Chu , Jianwei Han , Limin Wang
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.
{"title":"Pyromellitic diimide-derived quaternary ammonium salts: Synthesis and application as efficient copper electroplating levelers","authors":"Fengyan Lu , Xuyang Li , Qi Zhu , Lifeng Chu , Jianwei Han , 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}
Pub Date : 2026-04-01Epub Date: 2025-12-24DOI: 10.1016/j.tet.2025.135126
Qin Li , Shanglin Li , Zhouyang Long , Minyi Liang , Zihao Yin , Pingbo Zhang , Yan Leng
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.
{"title":"Synthesis of novel naphthopyran dyes and their photochromic properties in resin lenses","authors":"Qin Li , Shanglin Li , Zhouyang Long , Minyi Liang , Zihao Yin , Pingbo Zhang , 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}
Pub Date : 2026-04-01Epub Date: 2025-12-17DOI: 10.1016/j.tet.2025.135106
Shi-Jiao Zhang , Yu Teng , Hong-Shuang Li
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(sp2)–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(sp2)–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.
{"title":"Transition-metal-catalyzed/mediated direct C(sp2)–H selenylation of heterocycles","authors":"Shi-Jiao Zhang , Yu Teng , 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}
Pub Date : 2026-04-01Epub Date: 2025-12-17DOI: 10.1016/j.tet.2025.135103
Mao-Lin Liao , Peng-Peng Liu , Chang-Liang Tan , Ping-Gui Li , Liang-Hua Zou
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.
{"title":"Advances in pyrazolone functionalization: A review since 2020","authors":"Mao-Lin Liao , Peng-Peng Liu , Chang-Liang Tan , Ping-Gui Li , 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}
Pub Date : 2026-04-01Epub Date: 2025-12-26DOI: 10.1016/j.tet.2025.135127
Zebabanu Khalifa, Amit B. Patel
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(sp2)-C(sp) bond between 4-hydroxyquinoline-3-carboxylic acid derivatives and structurally diverse terminal alkynes via dual C–O/C–H functionalization. This facile protocol has offered significant economic value due to its in situ 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(sp2)-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 N-heteroaromatic scaffolds, offering significant potential for material synthesis, molecular diversification, and chemotherapeutic innovations by involving palladium-catalyzed decarbonylative Sonogashira cross-coupling.
通过优化一系列钯催化体系，揭示了一种通用的、原子高效的、可持续的脱碳Sonogashira交叉偶联方法，该方法可以通过双C - o /C -h功能化在4-羟基喹啉-3-羧酸衍生物和结构多样的末端炔之间直接构建C(sp2)-C（sp）键。由于其原位功能和良好的耐受底物范围，这种简单的方案提供了显着的经济价值，可提供高达88%的合理产率，并且产生最少的副产品。此外，机理研究揭示了钯配体活性物质的效率，为单一催化体系中脱羰C(sp2)-C（sp）交叉偶联途径提供了有价值的见解。因此，本研究为n -杂芳烃支架的后期功能化提供了一条可靠和可持续的途径，通过钯催化脱碳Sonogashira交叉偶联，为材料合成、分子多样化和化疗创新提供了巨大的潜力。
{"title":"Palladium-catalyzed decarbonylative alkynylation of hydroxyquinoline carboxylic acid using dual C–H/C–O bond activation","authors":"Zebabanu Khalifa, 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}
Pub Date : 2026-04-01Epub Date: 2025-12-17DOI: 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
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.
{"title":"Diels-Alder reaction: A versatile synthetic tool for the synthesis of terpenoids and alkaloids: A review","authors":"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","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}
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.
{"title":"Gram-scale reduction of esters to alcohols using AlCl3/NaBH4 revisited: Solvent effect, scope, and limitations","authors":"Hai-yang Chen , Eman Fayad , Dalal Nasser Binjawhar , 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}
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