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Synthesis of Benzo-Fused Cycloheptanones from Cyclobutanol Derivatives by a C-C Cleavage/Cross-Coupling/Enolate Arylation Sequence. 环丁醇衍生物C-C裂解/交叉偶联/烯酸酯芳基化合成苯并融合环庚酮。
IF 2.2 4区 化学
Synthesis-Stuttgart Pub Date : 2025-06-01 Epub Date: 2025-04-14 DOI: 10.1055/s-0043-1775469
Gwyneth L Pudner, Selena Dessain, Eric K Wu, Richmond Sarpong
{"title":"Synthesis of Benzo-Fused Cycloheptanones from Cyclobutanol Derivatives by a C-C Cleavage/Cross-Coupling/Enolate Arylation Sequence.","authors":"Gwyneth L Pudner, Selena Dessain, Eric K Wu, Richmond Sarpong","doi":"10.1055/s-0043-1775469","DOIUrl":"10.1055/s-0043-1775469","url":null,"abstract":"<p><p>Herein, we describe a convergent method for the synthesis of benzo-fused cycloheptanones from cyclobutanol derivatives and 1,2-dihaloarene electrophiles. The inherent ring strain of the cyclobutanol coupling partner is leveraged to drive a Pd-catalyzed C-C cleavage/cross-coupling. A subsequent intramolecular enolate arylation results in the formation of the benzo-fused seven-membered carbocycle in a one-pot sequence. A range of electronically diverse 1,2-dihaloarene electrophiles as well as various substituted cyclobutanols were investigated as cross-coupling partners.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 12","pages":"1982-1996"},"PeriodicalIF":2.2,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12705038/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145769698","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Pyrazol-3-yldiazonium Salts as Key Reagents for C–C Bond Formation and Pyrazole-Containing Heterocycle Synthesis 吡唑-3-基重氮盐作为C-C键形成和含吡唑杂环合成的关键试剂
4区 化学
Synthesis-Stuttgart Pub Date : 2025-05-20 DOI: 10.1055/s-0043-1773546
Andreas Schmidt, Yu. V. Ostapiuk, Oksana V. Barabash, Mary Y. Ostapiuk, Mykola Kravets, Мыкола Д. Обушак
{"title":"Pyrazol-3-yldiazonium Salts as Key Reagents for C–C Bond Formation and Pyrazole-Containing Heterocycle Synthesis","authors":"Andreas Schmidt, Yu. V. Ostapiuk, Oksana V. Barabash, Mary Y. Ostapiuk, Mykola Kravets, Мыкола Д. Обушак","doi":"10.1055/s-0043-1773546","DOIUrl":"https://doi.org/10.1055/s-0043-1773546","url":null,"abstract":"Abstract A novel application of 1-methylpyrazol-3-yldiazonium salts in the Meerwein reaction was introduced. These diazonium salts reacted with α,β-unsaturated functionalized compounds under Meerwein reaction conditions to yield pyrazole-containing building blocks, which subsequently allowed cyclization reactions with bisnucleophiles for the synthesis of pyrazol-3-yl-containing heterocyclic systems. In this way, pyrazole-containing heterocyclic compounds with 2-aminothiazole, 2-aminoselenazole, thiazolidin-4-one, selenazolidin-4-one, 3-hydroxythiophene, and 3-aminothiophene rings were efficiently prepared.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 15","pages":"2351-2362"},"PeriodicalIF":0.0,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147907392","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: 1
Concise Synthesis of Ethericins A and B, C10-Deoxygerfelin, and Diorcinol 乙醚素A、B、c10 -脱氧菌素和二羟苯甲醚的简明合成
4区 化学
Synthesis-Stuttgart Pub Date : 2025-05-05 DOI: 10.1055/s-0043-1775483
Yang Chen, Shuzhong He, Di Li, Ai Long, Yang Li, Qingping Zeng, Lan Yang
{"title":"Concise Synthesis of Ethericins A and B, C10-Deoxygerfelin, and Diorcinol","authors":"Yang Chen, Shuzhong He, Di Li, Ai Long, Yang Li, Qingping Zeng, Lan Yang","doi":"10.1055/s-0043-1775483","DOIUrl":"https://doi.org/10.1055/s-0043-1775483","url":null,"abstract":"Abstract Naturally occurring diaryl ethers exhibit significant potential for pharmaceutical and agricultural applications owing to their diverse biological activities. Previous synthetic approaches to these bioactive molecules have predominantly focused on developing novel aryl–O–aryl bond formation methodologies. In this study, a two-phase synthetic strategy is presented, comprising a coupling phase establishing the ethereal linkage through SNAr reaction between simple aryl substrates, followed by a functionalization phase enabling precise introduction of diverse substituents through C–H activation and subsequent cross-coupling transformations. This modular approach has enabled the efficient synthesis of four natural products: ethericin A, ethericin B, C10-deoxygerfelin, and diorcinol.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 13","pages":"2101-2104"},"PeriodicalIF":0.0,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147894390","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
Chitosan-Promoted Reduction of Nitroaromatics by B2(NMe2)4 under Wet Ball Milling Conditions 壳聚糖促进B2(NMe2)4在湿球磨条件下还原硝基芳烃
4区 化学
Synthesis-Stuttgart Pub Date : 2025-04-23 DOI: 10.1055/a-2593-4458
Xiuqiang Lu, Yuhang Su, Jingyan Chen, Hui Lin, Conglong Lin, Yuanzhi Lin
{"title":"Chitosan-Promoted Reduction of Nitroaromatics by B2(NMe2)4 under Wet Ball Milling Conditions","authors":"Xiuqiang Lu, Yuhang Su, Jingyan Chen, Hui Lin, Conglong Lin, Yuanzhi Lin","doi":"10.1055/a-2593-4458","DOIUrl":"https://doi.org/10.1055/a-2593-4458","url":null,"abstract":"Abstract The environmentally friendly reduction of nitro compounds to their corresponding amino compounds has been a practical and challenging task. In this paper, a method has been developed for the reduction of nitroaromatics to aromatic amines by ball milling. The method uses cheap and available tetrakis(dimethylamino)diboron as the reducing agent and NaOH as the base, and the reduction reaction can be achieved by wet ball milling assisted by chitosan. A range of nitroaromatic compounds containing a variety of alkyl, halogen, polynitro, and other groups were chemoselectively reduced to the corresponding anilines in good yields. This protocol will enrich functional group transformations of nitroaromatics to amines.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 16","pages":"2456-2461"},"PeriodicalIF":0.0,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147890242","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
A Green and Efficient Synthesis of 3-Hydroxy-4-methoxycinnamaldehyde via a Calcium Oxide–Ethanol Heterogeneous System 氧化钙-乙醇非均相体系绿色高效合成3-羟基-4-甲氧基肉桂醛
4区 化学
Synthesis-Stuttgart Pub Date : 2025-03-17 DOI: 10.1055/a-2560-7930
Junzhang Li, Boxun Duan, Jiangyuan Sun, Zhan Deng
{"title":"A Green and Efficient Synthesis of 3-Hydroxy-4-methoxycinnamaldehyde via a Calcium Oxide–Ethanol Heterogeneous System","authors":"Junzhang Li, Boxun Duan, Jiangyuan Sun, Zhan Deng","doi":"10.1055/a-2560-7930","DOIUrl":"https://doi.org/10.1055/a-2560-7930","url":null,"abstract":"Abstract 3-Hydroxy-4-methoxycinnamaldehyde is an important organic intermediate primarily synthesized via the aldol condensation of isovanillin and vinyl acetate. Traditional synthetic processes typically employ sodium hydroxide in aqueous solution, which results in low product yields and generates large quantities of wastewater. In this study, calcium oxide is utilized as an alternative to sodium hydroxide, and the aldol condensation is carried out in anhydrous ethanol. Calcium oxide not only serves as a basic catalyst for the aldol condensation reaction but also reacts with the generated water to form calcium hydroxide, thereby removing water from the reaction system. This effectively shifts the equilibrium of the aldol condensation reaction, leading to a higher conversion rate of isovanillin and a significantly improved yield of 3-hydroxy-4-methoxycinnamaldehyde, reaching 85.2%. This study provides a novel and efficient green synthetic approach to 3-hydroxy-4-methoxycinnamaldehyde, offering significant potential for industrial applications.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 12","pages":"1965-1974"},"PeriodicalIF":0.0,"publicationDate":"2025-03-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147891229","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
Cobalt-Catalyzed Regioselective Hydroformylation of Allylic Alcohol Esters 钴催化丙烯醇酯的区域选择性氢甲酰化反应
4区 化学
Synthesis-Stuttgart Pub Date : 2025-01-11 DOI: 10.1055/a-2515-0227
Wenxin Lu, Qinglei Chong, Fanke Meng, Zhao Du
{"title":"Cobalt-Catalyzed Regioselective Hydroformylation of Allylic Alcohol Esters","authors":"Wenxin Lu, Qinglei Chong, Fanke Meng, Zhao Du","doi":"10.1055/a-2515-0227","DOIUrl":"https://doi.org/10.1055/a-2515-0227","url":null,"abstract":"Abstract Aliphatic aldehydes are important building blocks in organic synthesis due to their high reactivity and versatility. Herein, we report a simple, mild and efficient method for the hydroformylation of allyl alcohol esters under cobalt catalysis. This procedure offers good functional group tolerance, moderate to good product yields and exclusive chemo- and regioselectivity, making it an attractive method to prepare aldehydes with linear selectivity.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 16","pages":"2434-2443"},"PeriodicalIF":0.0,"publicationDate":"2025-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147886802","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
Nickel(II)-Catalyzed Cycloisomerization of 1,6-Dienes 镍（II）催化1,6-二烯环异构化
4区 化学
Synthesis-Stuttgart Pub Date : 2025-01-03 DOI: 10.1055/a-2508-3790
Zhongjian Du, Chenlei Ji, Xu Wang, Sijian Zhang, Zhenyu Wang, Yang’en You
{"title":"Nickel(II)-Catalyzed Cycloisomerization of 1,6-Dienes","authors":"Zhongjian Du, Chenlei Ji, Xu Wang, Sijian Zhang, Zhenyu Wang, Yang’en You","doi":"10.1055/a-2508-3790","DOIUrl":"https://doi.org/10.1055/a-2508-3790","url":null,"abstract":"Abstract A nickel-catalyzed protocol for the cycloisomerization of 1,6-dienes has been developed. Using commercially available NiBr₂ and PPh₃ as catalysts, Zn as a reductant, and ZnI₂ as an additive, the methodology efficiently converts various 1,6-dienes into pyrrolidine derivatives in excellent yields and high selectivity.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 07","pages":"1306-1312"},"PeriodicalIF":0.0,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147915843","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: 2
Controllable Hydrodebromination of Tribromomethyl Groups via Lewis Base–Borane-Mediated Ionic and Radical Pathways 路易斯碱-硼烷介导的离子和自由基途径对三溴甲基的可控氢脱溴反应
4区 化学
Synthesis-Stuttgart Pub Date : 2025-01-02 DOI: 10.1055/s-0043-1773511
Feng‐Lian Zhang, Yi‐Feng Wang, Yan Liu, Yee Lin Phang, Ji‐Kang Jin, Wenping Xu
{"title":"Controllable Hydrodebromination of Tribromomethyl Groups via Lewis Base–Borane-Mediated Ionic and Radical Pathways","authors":"Feng‐Lian Zhang, Yi‐Feng Wang, Yan Liu, Yee Lin Phang, Ji‐Kang Jin, Wenping Xu","doi":"10.1055/s-0043-1773511","DOIUrl":"https://doi.org/10.1055/s-0043-1773511","url":null,"abstract":"Abstract Compounds bearing mono- and dibromomethyl groups are extensively utilized in synthetic and medicinal chemistry. In this regard, selective debromination of readily or easily accessible tribromomethyl compounds offers a direct and efficient method to access those two moieties. In this work, we introduced Lewis base–borane-mediated selective hydrodebromination of tribromomethyl groups via ionic or radical pathway. Using 4-(dimethylamino)pyridine–borane (DMAP-BH3) as a hydride donor, monohydrodebromination of tribromomethyl groups was achieved via nucleophilic substitution by hydride, delivering dibromomethyl groups. On the other hand, treatment of tribromomethyl compounds with an N-heterocyclic carbene–borane (NHC-BH2CN) as a boryl radical precursor in the presence of dilauroyl peroxide (DLP) as radical initiator afforded monobromomethyl compounds through consecutive bromine atom abstractions to cleave two C–Br bonds. Various tribromomethyl group bearing acetamides and acetates were applied in this developed protocol, showcasing good functional group tolerance and broad substrate scope.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 17","pages":"2620-2632"},"PeriodicalIF":0.0,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147897840","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
RNHSO2F as Reliable Azasulfene Precursors for the Construction of Sulfamates RNHSO2F作为构建氨基磺酸盐的可靠偶氮磺胺前体
4区 化学
Synthesis-Stuttgart Pub Date : 2024-12-26 DOI: 10.1055/a-2508-3355
Long Xu, Jiajia Dong, Taijie Guo, Wei Wang
{"title":"RNHSO2F as Reliable Azasulfene Precursors for the Construction of Sulfamates","authors":"Long Xu, Jiajia Dong, Taijie Guo, Wei Wang","doi":"10.1055/a-2508-3355","DOIUrl":"https://doi.org/10.1055/a-2508-3355","url":null,"abstract":"Abstract The utilization of NH-sulfamoyl fluorides (RNHSO2F) as reliable SuFEx synthons for the construction of various sulfamate esters is reported. By using potassium fluoride as base, we were able to convert RNHSO2F into azasulfene intermediates under mild conditions and guarantee their further efficient ligation with phenols and alcohols.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 05","pages":"978-990"},"PeriodicalIF":0.0,"publicationDate":"2024-12-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147902913","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: 2
Synthesis of 3,5-Disubstituted Anilines via Sequential Mo-Catalyzed Deoxygenative Benzene Formation and Pd-Catalyzed Amination Reactions 顺序mo催化脱氧苯生成和pd催化胺化反应合成3,5-二取代苯胺
4区 化学
Synthesis-Stuttgart Pub Date : 2024-12-17 DOI: 10.1055/a-2504-3357
Gang Fang, Yi-Zhe Yu, Chun‐Xiang Zhuo
{"title":"Synthesis of 3,5-Disubstituted Anilines via Sequential Mo-Catalyzed Deoxygenative Benzene Formation and Pd-Catalyzed Amination Reactions","authors":"Gang Fang, Yi-Zhe Yu, Chun‐Xiang Zhuo","doi":"10.1055/a-2504-3357","DOIUrl":"https://doi.org/10.1055/a-2504-3357","url":null,"abstract":"Abstract The substituted anilines play a pivotal role as structural motifs in agrochemicals, organic polymers, and pharmaceuticals, and great efforts have been dedicated to advancing their synthesis. However, the highly efficient and selective synthesis of meta,meta-disubstituted anilines remains a challenge. Here, the synthesis of meta,meta-disubstituted anilines via sequential Mo-catalyzed deoxygenative benzene formation and Pd-catalyzed amination reactions is reported. By employing this method, a wide range of meta,meta-disubstituted anilines were accessed with up to 89% yield from readily accessible ynones, allylic amines, and amines.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 12","pages":"1922-1927"},"PeriodicalIF":0.0,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147891786","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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