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Recent advances in Chan-Evans-Lam-type synthesis of ionic compounds chan - evans - lam型离子化合物合成研究进展
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-10-17 DOI: 10.1016/j.tetlet.2025.155866
Ao Wen, Baobao Su, Suci Meng, Huachen Lin, Zhibin Luo, Bin Liu
{"title":"Recent advances in Chan-Evans-Lam-type synthesis of ionic compounds","authors":"Ao Wen,&nbsp;Baobao Su,&nbsp;Suci Meng,&nbsp;Huachen Lin,&nbsp;Zhibin Luo,&nbsp;Bin Liu","doi":"10.1016/j.tetlet.2025.155866","DOIUrl":"10.1016/j.tetlet.2025.155866","url":null,"abstract":"<div><div>Since 2021, Chan–Evans–Lam (CEL) chemistry has expanded beyond classical protic nucleophiles to enable the synthesis of diverse onium salts from weakly nucleophilic or aprotic heteroatom substrates. Copper-mediated coupling of boronic acids with nitriles, <em>N</em>-heterocycles, thioethers, sulfenamides, thioureas, and phosphines now delivers nitrogen-, sulfur-, and phosphorus-centered onium salts under mild conditions. These advances significantly broaden the synthetic utility of CEL reactions, while persistent challenges with tertiary amines and general ethers delineate critical frontiers for future development.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155866"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145335020","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Pd(II)-catalyzed enantioselective C(sp2)–H ortho arylation toward the synthesis of P-stereogenic phosphinamides Pd（II）催化的对映选择性C(sp2) -H邻位芳基化反应合成p -立体磷酸酰胺
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-11-13 DOI: 10.1016/j.tetlet.2025.155898
Peng Xu , Yu-Xing Chen , Xuan Ni , Xu-Long Qin
{"title":"Pd(II)-catalyzed enantioselective C(sp2)–H ortho arylation toward the synthesis of P-stereogenic phosphinamides","authors":"Peng Xu ,&nbsp;Yu-Xing Chen ,&nbsp;Xuan Ni ,&nbsp;Xu-Long Qin","doi":"10.1016/j.tetlet.2025.155898","DOIUrl":"10.1016/j.tetlet.2025.155898","url":null,"abstract":"<div><div><em>P</em>-Stereogenic phosphorus compounds are important chiral ligands and highly efficient small molecule organocatalysts. In this study, we report Pd(II)-catalyzed enantioselective C(sp<sup>2</sup>)−H arylation of phosphinamide using directing group with diaryliodonium triflates. The reaction employs an inexpensive commercially available <em>L</em>-Phe-OH derivative as the chiral ligand. Through desymmetrization, this method was verified to afford the desired products in moderate yield with good enantioselectivity, demonstrating broad substrate scope and improved functional group tolerance.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155898"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145576486","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Photoinduced arylation of 3-acyl-substituted indoles with diaryliodonium triflates enabled by electron donor − acceptor complexes 电子供体-受体配合物使3-酰基取代吲哚与三氟酸二芳基碘鎓的光诱导芳基化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-11-08 DOI: 10.1016/j.tetlet.2025.155892
Yu-Tao Sun , Jing-Yao Zhou , Dong-En Wu , Mei Hong , Liang Wang
{"title":"Photoinduced arylation of 3-acyl-substituted indoles with diaryliodonium triflates enabled by electron donor − acceptor complexes","authors":"Yu-Tao Sun ,&nbsp;Jing-Yao Zhou ,&nbsp;Dong-En Wu ,&nbsp;Mei Hong ,&nbsp;Liang Wang","doi":"10.1016/j.tetlet.2025.155892","DOIUrl":"10.1016/j.tetlet.2025.155892","url":null,"abstract":"<div><div>Enabled by the formation of electron donor−acceptor complexes, a photoinduced arylation of 3-acyl-substituted indoles using diaryliodonium triflate as the arylation reagent has been disclosed. No photocatalyst, oxidant or base are required for this transformation. The direct irradiation of the mixture of 3-acyl-substituted indoles and diaryliodonium triflates under visible light in acetonitrile afforded 2-aryl indoles in moderate to good yields.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155892"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145525925","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Revisit the progress in the Ugi reaction: notable advances in synthesis and applications 回顾Ugi反应的进展：合成和应用方面的重大进展
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-11-08 DOI: 10.1016/j.tetlet.2025.155893
Suchandra Bhattacharjee, Sushmita Gajurel
{"title":"Revisit the progress in the Ugi reaction: notable advances in synthesis and applications","authors":"Suchandra Bhattacharjee,&nbsp;Sushmita Gajurel","doi":"10.1016/j.tetlet.2025.155893","DOIUrl":"10.1016/j.tetlet.2025.155893","url":null,"abstract":"<div><div>The Ugi reaction is one of the prevailing multicomponent reactions (MCR) and has evolved into a vital part of contemporary synthetic chemistry. In recent years, using alternate reagents for the Ugi reaction and developing new catalysts have significantly expanded the substrate scope of this specific reaction. The reactions are increasingly being used in novel ways, particularly in materials science and medicinal chemistry. Therefore, there is a need for a comprehensive review article that helps to summarize the existing research articles, provides a relative analysis, and identifies the research gap. This mini review considers the recent developments in Ugi chemistry, mainly from the period 2020–2025, emphasizing the significant advances in reaction conditions, key innovations in substrate diversity, and their applications in medicinal chemistry, including site-selective protein bioconjugation and drug developments. Great attention is placed on the sustainable synthetic approaches, including the use of nano- and photocatalysts, visible-light-mediated synthesis, and the Ugi products synthesized from plant extracts. The review also highlights the advances in enantioselective Ugi reactions facilitated by chiral catalysts and the development of atropisomeric scaffolds. Besides these, it explores the growing utility of the reaction in constructing complex molecular architectures like heterocycles, spirocycles, peptidomimetics, glycomimetics, and functional polymers. In general, this article presents a detailed and current overview of the changing landscape of the Ugi chemistry and outlines future guidelines for its application in both academic as well as commercial research.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155893"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145526006","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Ophiogluconoid A: The first pimarane-type diterpenoid glucoside with immunosuppressive activity from Ophiorrhiza brevidentata 蛇皮葡萄素A：首个从蛇皮根中提取的具有免疫抑制活性的海马烷型二萜糖苷
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-11-01 DOI: 10.1016/j.tetlet.2025.155880
Jia-Yu Jin , Fan Xu , Chun-Hao Du , Li-Na Zou , Ting Huang , Qin Ma , Ping Zhao , Zheng-Hui Li , Bao-Bao Shi , Ji-Kai Liu
{"title":"Ophiogluconoid A: The first pimarane-type diterpenoid glucoside with immunosuppressive activity from Ophiorrhiza brevidentata","authors":"Jia-Yu Jin ,&nbsp;Fan Xu ,&nbsp;Chun-Hao Du ,&nbsp;Li-Na Zou ,&nbsp;Ting Huang ,&nbsp;Qin Ma ,&nbsp;Ping Zhao ,&nbsp;Zheng-Hui Li ,&nbsp;Bao-Bao Shi ,&nbsp;Ji-Kai Liu","doi":"10.1016/j.tetlet.2025.155880","DOIUrl":"10.1016/j.tetlet.2025.155880","url":null,"abstract":"<div><div>Chemical investigation of the secondary metabolites of the aerial parts of <em>Ophiorrhiza brevidentata</em> H. S. Lo resulted in the isolation of a new pimarane-type diterpenoid glucoside, named ophiogluconoid A (<strong>1</strong>), along with a known biogenic precursor (<strong>2</strong>). Their structures were elucidated through extensive spectroscopic analysis. Ophiogluconoid A represents the first diterpenoid isolated from genus <em>Ophiorrhiza</em>. Additionally, it inhibited ConA-induced T cell proliferation (IC<sub>50</sub> = 4.3 μM) and LPS-induced B cell proliferation (IC<sub>50</sub> = 1.6 μM), demonstrating excellent selectivity indices (SI &gt; 10).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155880"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145463896","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Copper-catalyzed cross-coupling of sulfonyl hydrazides with aryl hydrazines to synthesize diaryl sulfones 铜催化磺酰肼与芳基肼交叉偶联合成二芳基砜
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-10-08 DOI: 10.1016/j.tetlet.2025.155845
E.V. Venkat Shivaji Ramarao , Jayshree Solanke , Rana Chatterjee , Rambabu Dandela
{"title":"Copper-catalyzed cross-coupling of sulfonyl hydrazides with aryl hydrazines to synthesize diaryl sulfones","authors":"E.V. Venkat Shivaji Ramarao ,&nbsp;Jayshree Solanke ,&nbsp;Rana Chatterjee ,&nbsp;Rambabu Dandela","doi":"10.1016/j.tetlet.2025.155845","DOIUrl":"10.1016/j.tetlet.2025.155845","url":null,"abstract":"<div><div>A simple and efficient method for the construction of symmetrical and unsymmetrical diaryl sulfones has been developed. Herein, Cu(OAc)<sub>2</sub>-catalyzed oxidative cross-coupling of aryl sulfonyl hydrazides and aryl hydrazine easily afforded the diaryl sulfones in the presence of K<sub>2</sub>CO<sub>3</sub> base and DMSO medium. Notably, a variety of diaryl sulfone derivatives have been synthesized in moderate to good yields.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155845"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145335017","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Rh(III)-catalyzed oxidative CH annulation of 3-arylisoquinolin-1-ones with diarylalkynes: Direct access to fused isoquinolinone frameworks Rh（III）催化3-芳基异喹啉-1- 1与二芳基炔的氧化CH环化：直接获得融合异喹啉酮框架
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-11-01 DOI: 10.1016/j.tetlet.2025.155871
S. Karthik , C. Sandhya , Ch. Ajay , B. Sridhar , B.V. Subba Reddy
{"title":"Rh(III)-catalyzed oxidative CH annulation of 3-arylisoquinolin-1-ones with diarylalkynes: Direct access to fused isoquinolinone frameworks","authors":"S. Karthik ,&nbsp;C. Sandhya ,&nbsp;Ch. Ajay ,&nbsp;B. Sridhar ,&nbsp;B.V. Subba Reddy","doi":"10.1016/j.tetlet.2025.155871","DOIUrl":"10.1016/j.tetlet.2025.155871","url":null,"abstract":"<div><div>A highly efficient Rh(III)-catalyzed oxidative C<img>H annulation of 3-arylisoquinolin-1-ones with diarylacetylenes has been developed for the synthesis of structurally diverse diaryl-8<em>H</em>-isoquinolino[3,2-<em>a</em>]isoquinolin-8-one scaffolds. This method offers special features such as excellent atom economy, broad substrate scope and high functional group tolerance, offering a valuable synthetic route for accessing polycyclic frameworks. It is a first example on the oxidative annulation of 3-arylisoquinolin-1-ones with alkynes employing a transition metal catalysis.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155871"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145414306","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
NaH-mediated synthesis of 3-hydroxy-2-oxindoles and their analogues from ortho-iodoaryl α-ketoamides 邻碘芳基α-酮酰胺催化合成3-羟基-2-氧吲哚及其类似物的研究
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-10-21 DOI: 10.1016/j.tetlet.2025.155870
Mengyang He , Qihui Wang , Tingting Yi , Xiaobei Chen , Xuejun Liu , Xiaodong Chen , Shilei Zhang , Yanwei Hu
{"title":"NaH-mediated synthesis of 3-hydroxy-2-oxindoles and their analogues from ortho-iodoaryl α-ketoamides","authors":"Mengyang He ,&nbsp;Qihui Wang ,&nbsp;Tingting Yi ,&nbsp;Xiaobei Chen ,&nbsp;Xuejun Liu ,&nbsp;Xiaodong Chen ,&nbsp;Shilei Zhang ,&nbsp;Yanwei Hu","doi":"10.1016/j.tetlet.2025.155870","DOIUrl":"10.1016/j.tetlet.2025.155870","url":null,"abstract":"<div><div>In our previous study, KH was employed as a metal-halogen exchange reagent to generate aryl anions for initiating the anionic Fries rearrangement. Herein, we demonstrate that cost-effective NaH can similarly activate ortho-iodoaryl α-ketoamide substrates <em>via</em> Na<img>I exchange with the aryl iodide moiety. The resultant aryl anions undergo intramolecular cyclization, efficiently affording 3-hydroxy-2-oxindoles or their heterocyclic analogues. Notably, these products can be further converted into other types of nitrogen-containing heterocycles, thereby establishing a platform for constructing diverse biologically important heterocyclic compounds for drug discovery.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155870"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145361385","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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-free fluorosulfonylation of cyclopropanol for the synthesis of aliphatic sulfonyl fluorides 环丙醇无过渡金属氟磺化合成脂肪族磺酰氟化合物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-10-23 DOI: 10.1016/j.tetlet.2025.155867
Jianquan Hong, Qiang Wang, Xifei Chen, Shengying Gu, Chunxiang Li, Jie Wang, Xinxin Gong, Xiaoyu Wang, Feng Zheng, Changge Zheng
{"title":"Transition metal-free fluorosulfonylation of cyclopropanol for the synthesis of aliphatic sulfonyl fluorides","authors":"Jianquan Hong,&nbsp;Qiang Wang,&nbsp;Xifei Chen,&nbsp;Shengying Gu,&nbsp;Chunxiang Li,&nbsp;Jie Wang,&nbsp;Xinxin Gong,&nbsp;Xiaoyu Wang,&nbsp;Feng Zheng,&nbsp;Changge Zheng","doi":"10.1016/j.tetlet.2025.155867","DOIUrl":"10.1016/j.tetlet.2025.155867","url":null,"abstract":"<div><div>We developed a practical synthesis method for aliphatic sulfonyl fluorides through transition metal-free fluorosulfonylation strategy. The reaction of cyclopropanol with K<sub>2</sub>S<sub>2</sub>O<sub>5</sub> and NFSI is enforced under mild conditions. This reaction system is suitable for cyclopropanols such as aryl, benzyl, and alkyl cyclopropanol, to achieve the corresponding sulfonyl fluoride compounds in moderate to good yields, wide substrate range, good compatibility, and simple operation.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155867"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145361387","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Disulfides as sulfonylation reagents for the synthesis of sulfonated spiro[5.5]trienones under metal free conditions 二硫化物作为磺化试剂在无金属条件下合成磺化螺[5.5]三烯酮
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-11-01 DOI: 10.1016/j.tetlet.2025.155872
Dong Xia , Jinghong Yang , Hao Peng , Lihu Zhang , Xiaobo Bao
{"title":"Disulfides as sulfonylation reagents for the synthesis of sulfonated spiro[5.5]trienones under metal free conditions","authors":"Dong Xia ,&nbsp;Jinghong Yang ,&nbsp;Hao Peng ,&nbsp;Lihu Zhang ,&nbsp;Xiaobo Bao","doi":"10.1016/j.tetlet.2025.155872","DOIUrl":"10.1016/j.tetlet.2025.155872","url":null,"abstract":"<div><div>A new facile one pot tandem sulfonylation and 6-<em>exo</em>-trig cyzlization/dearomatization of biaryl ynones was developed. Under metal free conditions, diversified sulfonated spiro[5.5]trienones were prepared using disulfides as sulfonylating reagents.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155872"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145463897","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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