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Efficient synthesis of chlorinated Dihydronaphthalene derivatives using N,N-diisopropylformamide-POCl3 as a Vilsmeier reagent 以N，N-二异丙基甲酰胺- pocl3为维斯迈试剂高效合成氯化二氢萘衍生物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-27 DOI: 10.1016/j.tetlet.2025.155726
Dinghao Li , Junwei Li , Yumeng Zhang, Fang-Lin Zhang
{"title":"Efficient synthesis of chlorinated Dihydronaphthalene derivatives using N,N-diisopropylformamide-POCl3 as a Vilsmeier reagent","authors":"Dinghao Li ,&nbsp;Junwei Li ,&nbsp;Yumeng Zhang,&nbsp;Fang-Lin Zhang","doi":"10.1016/j.tetlet.2025.155726","DOIUrl":"10.1016/j.tetlet.2025.155726","url":null,"abstract":"<div><div>A newly developed chlorinating reagent (<em>N,N</em>-diisopropylformamide-POCl<sub>3</sub> complex) and metal halide (ZnCl<sub>2</sub>) synergistic reaction system was reported for the efficient chlorination of polysubstituted 1-tetralones. This protocol facilitates the reaction to proceed under mild conditions with this in situ formed Vilsmeier reagent, and a broad substrate scope could be compatible. 28 examples were successfully converted to the corresponding chlorodihydronaphthalenes in moderate to good yields, meanwhile significantly suppressing the formation of halogenated enal byproducts. The simplicity, high efficiency and wide substrate compatibility enable this new method to be a promising alternative for the synthesis of halogenated aryl olefins and drug molecules.</div><div>2009 Elsevier Ltd. All rights reserved.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155726"},"PeriodicalIF":1.5,"publicationDate":"2025-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144570344","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
[Ni(PnBu3)2Cl2] as an economical precatalyst for the Suzuki-Miyaura cross coupling reaction of aryl sulfonate esters and halides [Ni(PnBu3)2Cl2]作为经济预催化剂用于芳基磺酸酯与卤化物的Suzuki-Miyaura交叉偶联反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-24 DOI: 10.1016/j.tetlet.2025.155723
Eric Fortin Constant, Armaan Grewal, Eric C. Keske
{"title":"[Ni(PnBu3)2Cl2] as an economical precatalyst for the Suzuki-Miyaura cross coupling reaction of aryl sulfonate esters and halides","authors":"Eric Fortin Constant,&nbsp;Armaan Grewal,&nbsp;Eric C. Keske","doi":"10.1016/j.tetlet.2025.155723","DOIUrl":"10.1016/j.tetlet.2025.155723","url":null,"abstract":"<div><div>The air stable precatalyst [Ni(PnBu<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub>] was successfully demonstrated to be highly active in the Suzuki-Miyaura reaction of aryl tosylates, mesylates and chlorides without the use of an external reducing agent. Biaryl products were typically formed in high yield without the requirement of large excesses of phenyl boronic acid derivatives or base. This precatalyst can be readily prepared from inexpensive starting materials representing a distinct economic advantage over previously reported precatalysts. We further report our computational studies indicating potential oxidative addition mechanisms with this precatalyst on aryl sulfonate electrophiles.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155723"},"PeriodicalIF":1.5,"publicationDate":"2025-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144556706","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
Organocatalytic asymmetric umpolung reaction of cyanoketimines with 2-(bromomethyl)acrylate 氰氯胺与2-（溴甲基）丙烯酸酯的有机催化不对称不对称反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-24 DOI: 10.1016/j.tetlet.2025.155722
Cheng Cheng, Yiru Pan, Yuhong Gao, Jisheng Luo, Li Deng
{"title":"Organocatalytic asymmetric umpolung reaction of cyanoketimines with 2-(bromomethyl)acrylate","authors":"Cheng Cheng,&nbsp;Yiru Pan,&nbsp;Yuhong Gao,&nbsp;Jisheng Luo,&nbsp;Li Deng","doi":"10.1016/j.tetlet.2025.155722","DOIUrl":"10.1016/j.tetlet.2025.155722","url":null,"abstract":"<div><div>Chiral α-aminonitriles are not only versatile synthons in chemical synthesis, but also exist as motifs in a wide range of biologically active molecules. Consequently, the catalytic asymmetric synthesis of chiral α-aminonitriles has attracted considerable attention. Despite these significant progresses, the catalytic asymmetric synthesis of chiral α-aminonitriles bearing other synthetically useful functionalities remains desirable. We reported a catalytic asymmetric synthesis of chiral α-aminonitriles bearing a 2‑carbonyl allyl group <em>via</em> a catalytic umpolung reaction of cyanoketimines with 2-(bromomethyl)acrylate. This reaction demonstrates broad substrate scope, accommodating a wide range of aryl, heteroaryl and alkyl cyanoketimines. Given that both the aminonitrile and the 2‑carbonyl allyl moieties are versatile synthons in asymmetric synthesis, we anticipate that this reaction will serve as a valuable method for drug discovery and construction of complex chiral molecules.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155722"},"PeriodicalIF":1.5,"publicationDate":"2025-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144518185","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 cyclization of N-propargyl-N-tosyl hydrazines: Facile preparation of 1,5-disubstituted pyrazoles 铜催化n -丙炔- n -甲酰基肼环化：1,5-二取代吡唑的简易制备
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-23 DOI: 10.1016/j.tetlet.2025.155721
Cheng-Cheng Wei, Yu-Mei Zhang, Yi Li, Mei-Hua Shen, Hua-Dong Xu
{"title":"Copper catalyzed cyclization of N-propargyl-N-tosyl hydrazines: Facile preparation of 1,5-disubstituted pyrazoles","authors":"Cheng-Cheng Wei,&nbsp;Yu-Mei Zhang,&nbsp;Yi Li,&nbsp;Mei-Hua Shen,&nbsp;Hua-Dong Xu","doi":"10.1016/j.tetlet.2025.155721","DOIUrl":"10.1016/j.tetlet.2025.155721","url":null,"abstract":"<div><div>A CuBr∙SMe<sub>2</sub> catalyzed intramolecular cyclization of N-tosy-N-propargyl hydrazine derivatives to form N-substituted pyrazoles was established, presumably, through a one-pot-two-step domino of 5-<em>endo</em>-dig cyclization and subsequent eliminative aromatization. Nineteen N-substituted pyrazoles were made with good to excellent yields.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155721"},"PeriodicalIF":1.5,"publicationDate":"2025-06-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144501090","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
Catalytic asymmetric synthesis and Stereocenter assignment of naturally occurring Sesquiterpenoid, (−)-Baccharisketone 催化不对称合成天然倍半萜类化合物(−)-双环酮的立体中心配位
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-21 DOI: 10.1016/j.tetlet.2025.155719
Debopam Pal , Dhruvilkumar Sureshkumar Patel , Vishnumaya Bisai
{"title":"Catalytic asymmetric synthesis and Stereocenter assignment of naturally occurring Sesquiterpenoid, (−)-Baccharisketone","authors":"Debopam Pal ,&nbsp;Dhruvilkumar Sureshkumar Patel ,&nbsp;Vishnumaya Bisai","doi":"10.1016/j.tetlet.2025.155719","DOIUrl":"10.1016/j.tetlet.2025.155719","url":null,"abstract":"<div><div>Catalytic asymmetric total synthesis of either enantiomer of naturally occurring sesquiterpenoid, i.e. (−)-baccharisketone (<strong>1a</strong>) and (+)-baccharisketone (<em>ent</em>-<strong>1a</strong>) has been achieved via a key catalytic asymmetric <em>p</em>-tolyl boronic acid addition onto <em>E</em>-ester. Thus, an efficient five-step approach to both enantiomers of baccharisketone has been shown using 2 mol% Rh(COD)<sub>2</sub>BF<sub>4</sub>-(<em>R</em>)-BINAP as catalyst to achieve the product with a stereogenic center at the pseudobenzylic position (up to 93 % ee). This also confirms the assignment of the stereogenic center present at the pseudobenzylic position.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155719"},"PeriodicalIF":1.5,"publicationDate":"2025-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144492066","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
Gold nanoparticles for selective aromatic fluorine substitution by Azide under moderate conditions: Insights and mechanistic studies via DFT 金纳米颗粒在中等条件下选择性叠氮化物取代芳族氟：通过DFT的见解和机理研究
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-19 DOI: 10.1016/j.tetlet.2025.155712
Mansi Dubey, Satyanand Kumar, Ravi Kumar, Satish Kumar Awasthi
{"title":"Gold nanoparticles for selective aromatic fluorine substitution by Azide under moderate conditions: Insights and mechanistic studies via DFT","authors":"Mansi Dubey,&nbsp;Satyanand Kumar,&nbsp;Ravi Kumar,&nbsp;Satish Kumar Awasthi","doi":"10.1016/j.tetlet.2025.155712","DOIUrl":"10.1016/j.tetlet.2025.155712","url":null,"abstract":"<div><div>A newer method was serendipitously discovered and exploited for the synthesis of various aromatic azides. By reacting fluoro-substituted aryl derivatives with sodium azide under conventional heating in DMF and using gold nanoparticles as suitable catalysts, selective aromatic fluorine substitution via the S<sub>N</sub>Ar mechanism was achieved. This approach led to the formation of some novel aromatic azides with high yields and shorter reaction times.<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (405KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155712"},"PeriodicalIF":1.5,"publicationDate":"2025-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144556705","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
ZnBr2 catalyzed sequential A3-coupling and intramolecular cyclization: One-pot synthesis of 3-aminofurans ZnBr2催化顺序a3偶联和分子内环化：一锅法合成3-氨基呋喃
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-19 DOI: 10.1016/j.tetlet.2025.155718
Battini Geetha Rani , Sreedhar Gundekari , Kola Ramesh , Chandra Sekhar Vasam , Narasimha Swamy Thirukovela
{"title":"ZnBr2 catalyzed sequential A3-coupling and intramolecular cyclization: One-pot synthesis of 3-aminofurans","authors":"Battini Geetha Rani ,&nbsp;Sreedhar Gundekari ,&nbsp;Kola Ramesh ,&nbsp;Chandra Sekhar Vasam ,&nbsp;Narasimha Swamy Thirukovela","doi":"10.1016/j.tetlet.2025.155718","DOIUrl":"10.1016/j.tetlet.2025.155718","url":null,"abstract":"<div><div>ZnBr<sub>2</sub> salt was observed to be an effective catalyst to promote domino A<sup>3</sup>-coupling and intramolecular cyclization for the synthesis of 3-aminofurans from simple and commercially available α-ketoaldehydes, secondary amines, and terminal alkynes as starting materials. This method is compatible with several substrates and attractive, due to the formation of water as a by-product, operational simplicity, atom-economy, shorter reaction time, and inexpensive catalyst.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155718"},"PeriodicalIF":1.5,"publicationDate":"2025-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144501394","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
t-BuOLi-promoted Knoevenagel condensation: An efficient approach for synthesizing Arylid-BOX t- buoli促进Knoevenagel缩合：一种合成芳基酰胺- box的有效方法
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-18 DOI: 10.1016/j.tetlet.2025.155706
Run He, Zilong Zhang, Yuxiang Zhou, Li Zeng, Lou Shi, Deqiang Liang
{"title":"t-BuOLi-promoted Knoevenagel condensation: An efficient approach for synthesizing Arylid-BOX","authors":"Run He,&nbsp;Zilong Zhang,&nbsp;Yuxiang Zhou,&nbsp;Li Zeng,&nbsp;Lou Shi,&nbsp;Deqiang Liang","doi":"10.1016/j.tetlet.2025.155706","DOIUrl":"10.1016/j.tetlet.2025.155706","url":null,"abstract":"<div><div>A <em>t</em>-BuOLi-promoted Knoevenagel condensation is reported, offering a straightforward method for the rapid construction of Arylid-BOX. This late-stage functionalization method of unsubstituted BOX ligands enables the rapid synthesis of a wide range of Arylid-BOX compounds. We speculate that the relatively small atomic radius of lithium ions contributes to the high yields of this reaction.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155706"},"PeriodicalIF":1.5,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144307133","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
Mercaptan-free approach to the synthesis of Ethiprole, an insecticide 无硫醇合成杀虫剂乙虫乐的方法
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-18 DOI: 10.1016/j.tetlet.2025.155713
Rachel Gundamalla , P. Naveen Reddy , RajashakerBantu , B.V. Subba Reddy
{"title":"Mercaptan-free approach to the synthesis of Ethiprole, an insecticide","authors":"Rachel Gundamalla ,&nbsp;P. Naveen Reddy ,&nbsp;RajashakerBantu ,&nbsp;B.V. Subba Reddy","doi":"10.1016/j.tetlet.2025.155713","DOIUrl":"10.1016/j.tetlet.2025.155713","url":null,"abstract":"<div><div>An efficient and practical method has been developed for the synthesis of a second-generation insecticide, ethiprole. The key step involved in this approach is the thiocynation of pyrazole ring at the 4th position, which was achieved using bromine and potassium thiocyanate in methanol. Another important step involves the one-pot conversion of thiocyanate into ethyl sulfide using ethyl bromide in the presence of a base. Each step in this synthesis was performed efficiently on a gram scale to produce high-quality product. This new synthetic strategy is simple, convenient and scalable.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155713"},"PeriodicalIF":1.5,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144329791","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
Total syntheses of anticancer Abietane Diterpenoids, (±)-Royleanone and (±)-Inuroyleanol via Lewis acid catalyzed Hydroarylation 路易斯酸催化氢化芳基化合成抗癌阿比烷二萜（±）-罗伊精酮和（±）-尿精醇
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-18 DOI: 10.1016/j.tetlet.2025.155715
Badrinath N. Kakde , Suman Noskar , Saikat Bag , Alakesh Bisai
{"title":"Total syntheses of anticancer Abietane Diterpenoids, (±)-Royleanone and (±)-Inuroyleanol via Lewis acid catalyzed Hydroarylation","authors":"Badrinath N. Kakde ,&nbsp;Suman Noskar ,&nbsp;Saikat Bag ,&nbsp;Alakesh Bisai","doi":"10.1016/j.tetlet.2025.155715","DOIUrl":"10.1016/j.tetlet.2025.155715","url":null,"abstract":"<div><div>Herein we report a Lewis acid-catalyzed intramolecular hydroarylation strategy enabling an efficient synthesis of [6,6,6]-fused abietane diterpenoids sharing a trans-decalin motif. Using bismuth(III) triflate as an efficient metal triflate, the key intermediates were prepared in high yields, facilitating concise total syntheses of royleanone (<strong>1a</strong>) and inuroyleanone (<strong>1c</strong>), showcasing a scalable approach to complex natural product frameworks.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155715"},"PeriodicalIF":1.5,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144329790","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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