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Chemo-/Regioselective [5+1] Annulation with gem-Difluoromethylene Allenes for the Assembly of Fluorinated 2H-Chromenes and Dihydroquinolines 化学/区域选择性[5+1]环化宝石-二氟亚甲基烯组装氟化2h -铬和二氢喹啉
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-12-03 DOI: 10.1002/adsc.202401110
Zhi Zhou, Zhensheng Lin, Ying Cai, Junwei Ye, Kaifeng Chen, Jieni Zheng, Linxin Zhou, Wei Yi
{"title":"Chemo-/Regioselective [5+1] Annulation with gem-Difluoromethylene Allenes for the Assembly of Fluorinated 2H-Chromenes and Dihydroquinolines","authors":"Zhi Zhou, Zhensheng Lin, Ying Cai, Junwei Ye, Kaifeng Chen, Jieni Zheng, Linxin Zhou, Wei Yi","doi":"10.1002/adsc.202401110","DOIUrl":"https://doi.org/10.1002/adsc.202401110","url":null,"abstract":"A variety of fluorinated 2H-chromenes and dihydroquinolines was synthesized by virtue of gem-difluoromethylene allenes as versatile coupling partners to participate in the transition metal-catalysed cascade C-H activation/[5+1] annulation of 2-alkenylphenols/anilines. This protocol features specific chemo-/regioselectivity, redox-neutral manner and good compatibility, providing a straightforward synthetic route to intriguing motifs with the equipment of attractive fluoroalkenyl moiety. The distinctive gem-difluorine effect induced an unexpected protonolysis of σ carbon-metal bond, thus accounting for the observed selectivity via sequential C-H activation/allene insertion/protonolysis/cyclization/β-F elimination process.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"47 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142763628","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Electrochemically Driven Site-Selective C(sp2)-H Bond Hydroxylation of N-Substituted Anilines 电化学驱动的n -取代苯胺的位点选择性C(sp2)-H键羟基化
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-12-02 DOI: 10.1002/adsc.202401349
Anil Dapkekar, Suman Kumar Nag, Gedu Satyanarayana
{"title":"Electrochemically Driven Site-Selective C(sp2)-H Bond Hydroxylation of N-Substituted Anilines","authors":"Anil Dapkekar, Suman Kumar Nag, Gedu Satyanarayana","doi":"10.1002/adsc.202401349","DOIUrl":"https://doi.org/10.1002/adsc.202401349","url":null,"abstract":"Organic synthesis has long been fascinated by phenolic compounds, especially their exploration of selectively hydroxylating arenes utilizing H2O as a hydroxyl source. However, phenols' low redox potential and strong reactivity frequently result in unwanted overoxidation byproducts. Here, we present an electrochemical strategy to overcome this difficulty by using electricity as an oxidant and facilitating the para-selective hydroxylation of N-protected anilines. This process exhibits excellent regio-selectivity, compatibility with diverse functional groups, and adaptability by handling an extensive range of substrates. Noteworthily, the technique provides a sustainable substitute for paracetamol synthesis and terminal acetylene-holding hydroxylated products, proving the suitability of this strategy for drug synthesis. Significantly, mechanistic investigations suggest the possible radical pathway and water as a hydroxyl source for this strategy.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"18 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142760245","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Photoredox-Catalyzed Minisci-Type Acylation of Heterocyclic C–H Bonds with Amino Acid-Tethered Dihydropyridines 光氧化催化与氨基酸系连二氢吡啶的杂环C-H键的迷你型酰化
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-29 DOI: 10.1002/adsc.202401394
Heesang Yang, Hyungjin Shin, Yeonhee Lee, Dabeen Lim, Na Yeon Kwon, AMITAVA RAKSHIT, Pargat Singh, Hyun Jin Kim, Kyeongwon Moon, In Su Kim
{"title":"Photoredox-Catalyzed Minisci-Type Acylation of Heterocyclic C–H Bonds with Amino Acid-Tethered Dihydropyridines","authors":"Heesang Yang, Hyungjin Shin, Yeonhee Lee, Dabeen Lim, Na Yeon Kwon, AMITAVA RAKSHIT, Pargat Singh, Hyun Jin Kim, Kyeongwon Moon, In Su Kim","doi":"10.1002/adsc.202401394","DOIUrl":"https://doi.org/10.1002/adsc.202401394","url":null,"abstract":"Conjugation of amino acids to bioactive molecules has emerged as a promising strategy for optimizing pharmacological profiles of lead candidates in drug discovery. This study describes a photocatalytic Minisci-type transfer reaction of N-acyl amino acids into various N-heterocycles. Notably, this protocol enables direct conjugation of amino acids into heterocyclic C–H bonds, eliminating the need for prefunctionalized substrates. A diverse array of N-heterocycles, amino acids, oligopeptides, and drugs were used to demonstrate the potential of the proposed approach. In addition, the importance of this approach is demonstrated through its application in the DNA-encoded library chemistry. Various synthetic transformations and preliminary mechanistic investigations were also explored.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"25 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142753419","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Methylthio Radical Generation from Methylthiophosphonium Salt 甲基硫代膦盐光诱导甲基硫自由基生成
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-29 DOI: 10.1002/adsc.202401331
Wenxin Tang, Xuening Li, Xiaodi Su, Zhusheng Yang, Gongjun Wang, He Sheng, Wei Gong, Fang Tan, Qiang Liu, Xiang-Yu Chen
{"title":"Photoinduced Methylthio Radical Generation from Methylthiophosphonium Salt","authors":"Wenxin Tang, Xuening Li, Xiaodi Su, Zhusheng Yang, Gongjun Wang, He Sheng, Wei Gong, Fang Tan, Qiang Liu, Xiang-Yu Chen","doi":"10.1002/adsc.202401331","DOIUrl":"https://doi.org/10.1002/adsc.202401331","url":null,"abstract":"The production of methylthio radical typically relies on gaseous methanethiol or dimethyl disulfide. Herein, we present a new and straightforward method for the photogeneration of methylthio radical from methylthiophosphonium salt, enabling the synthesis of methylthiophenanthridines via charge transfer complex strategy. In this approach, the methylthiophosphonium salt acts as the electron acceptor, while 2-isocyanobiaryls serve as the electron donors. This strategy is distinguished by its simplicity in both conditions and operation, and can be extended for the generation of various alkyl(aryl)thio radicals.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"64 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142753421","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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-Catalyzed Denitrative C2-Arylation of Oxazoles, Benzoxazoles, and Benzimidazoles with Nitroarenes pd催化恶唑、苯并恶唑和苯并咪唑与硝基芳烃的c2 -芳基化反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-29 DOI: 10.1002/adsc.202401332
Lin Feng, Haiyan Li, Lei Huang, Jiaxin Yao, Wengui Duan, Lin Yu
{"title":"Pd-Catalyzed Denitrative C2-Arylation of Oxazoles, Benzoxazoles, and Benzimidazoles with Nitroarenes","authors":"Lin Feng, Haiyan Li, Lei Huang, Jiaxin Yao, Wengui Duan, Lin Yu","doi":"10.1002/adsc.202401332","DOIUrl":"https://doi.org/10.1002/adsc.202401332","url":null,"abstract":"A step-economic method for C2-arylated azoles via Pd-catalyzed denitrative arylation of nitroarenes and azoles is reported. This protocol employs synthetically upstream nitroarenes as arylating reagents and proceeds through the selective cleavage of the C–NO<sub>2 </sub>and C–H bonds. Various nitroarenes and nitroheteroarenes were coupled with oxazoles, benzoxazoles, and methylbenzimidazoles, achieving yields of up to 95%. The method's utility is exemplified by its application in the synthesis of Flunoxaprofen. This strategy reduces synthetic steps and minimizes pollution, offering substantial cost-effectiveness and environmental benefits. Furthermore, the relatively inert C–NO<sub>2</sub> bond in nitroarenes enables late-stage functionalization or stepwise coupling reactions, providing a complementary method for C2-arylation of azoles.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"6 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142753420","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Recent Developments in Synthetic Methodologies for Isochromenes 等色胺合成方法的最新进展
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-29 DOI: 10.1002/adsc.202401241
Marcelo H. R. Carvalho, Guilherme Machado Martins, Giovanni Amarante, Pedro de Castro
{"title":"Recent Developments in Synthetic Methodologies for Isochromenes","authors":"Marcelo H. R. Carvalho, Guilherme Machado Martins, Giovanni Amarante, Pedro de Castro","doi":"10.1002/adsc.202401241","DOIUrl":"https://doi.org/10.1002/adsc.202401241","url":null,"abstract":"Isochromenes, oxygen-containing bicyclic compounds, have gained significant attention in organic synthesis due to their versatile reactivity and prominence in biologically active natural products. This review highlights recent developments in the synthesis of isochromenes, with a focus on efficient and selective methodologies. Traditional metal-catalyzed intramolecular ring-closure reactions have been the cornerstone for isochromene formation, but recent efforts have expanded to include new strategies that enhance functionalization and scalability. By examining key advancements in the field, this article provides a critical assessment of the current state of the art involving isochromene synthesis and its ongoing challenges.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"200 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142753416","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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-mediated C-H functionalization of amines, imines, and amides: Recent developments and synthetic applications 铜介导的胺、亚胺和酰胺的C-H功能化：最新进展和合成应用
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-29 DOI: 10.1002/adsc.202401245
Priyanka Nath, Aditi Boruah, Mohit L. Deb, Pranjal Baruah
{"title":"Copper-mediated C-H functionalization of amines, imines, and amides: Recent developments and synthetic applications","authors":"Priyanka Nath, Aditi Boruah, Mohit L. Deb, Pranjal Baruah","doi":"10.1002/adsc.202401245","DOIUrl":"https://doi.org/10.1002/adsc.202401245","url":null,"abstract":"Copper-mediated C-H functionalization has emerged as a powerful strategy for the selective modification of nitrogen-containing molecules, offering significant advancements in organic synthesis. This review provides a comprehensive overview of recent developments in copper-catalyzed C-H functionalization reactions of amines, imines, and amides, from 2013 to present, emphasizing their synthetic applications and mechanistic insights. It also discusses the impact of these methodologies on the construction of complex molecular architectures, including pharmaceuticals and natural products. This review aims to provide valuable guidance for researchers seeking to leverage copper-mediated strategies in their synthetic endeavors by creating current knowledge and identifying future directions. We have highlighted the new bonds formed through C-H functionalizations for the convenience of readers.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"84 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142753418","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Selective Enzymatic C-H-Oxyfunctionalization for the Efficient Synthesis of Grevillic Acid 选择性酶催化c - h -氧官能化高效合成甘草酸
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-28 DOI: 10.1002/adsc.202401421
Clemens Cziegler, Benjamin Baumert, Christoffel P. S. Badenhorst, Karsten Siems, Uwe Bornscheuer
{"title":"Selective Enzymatic C-H-Oxyfunctionalization for the Efficient Synthesis of Grevillic Acid","authors":"Clemens Cziegler, Benjamin Baumert, Christoffel P. S. Badenhorst, Karsten Siems, Uwe Bornscheuer","doi":"10.1002/adsc.202401421","DOIUrl":"https://doi.org/10.1002/adsc.202401421","url":null,"abstract":"In this study, a selective C-H oxyfunctionalization using an unspecific peroxygenase (UPO) enabled an efficient biosynthetic route for the synthesis of grevillic acid (GA), a natural antioxidant. The route commenced with the release of o-coumaric acid (oCA) from trans-2-coumaric acid glucoside (trans-CAG) using commercially available ꞵ-glucosidase from almonds. In addition, a cis-to-trans photoisomerization of cis-CAG was implemented to increase the synthetic access of oCA. The key step, the para-hydroxylation relative to the existing hydroxyl group of oCA, was accomplished by an UPO with full conversion and 93% isolated yield. Despite its name, the UPO turned out to exhibit excellent regioselectivity in this C-H functionalization, requiring only H2O2 as a cosubstrate.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"6 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142753422","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Phosphonamidates of Camphorsultam: Versatile Building Blocks for the Synthesis of P‐Chiral Phosphorous(V) Compounds 樟脑磺酰胺：合成 P 手性磷（V）化合物的多功能基石
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-27 DOI: 10.1002/adsc.202401268
Yasutomo Yamamoto, Yurika Kambara, Ayase Matsumoto, Miku Murata, Mizuki Nakamoto, Tomoe Ishiura, Sakura Nakai, Hideyasu China, Kenji Watanabe, Akari Miyawaki, Junpei Matsuoka
{"title":"Phosphonamidates of Camphorsultam: Versatile Building Blocks for the Synthesis of P‐Chiral Phosphorous(V) Compounds","authors":"Yasutomo Yamamoto, Yurika Kambara, Ayase Matsumoto, Miku Murata, Mizuki Nakamoto, Tomoe Ishiura, Sakura Nakai, Hideyasu China, Kenji Watanabe, Akari Miyawaki, Junpei Matsuoka","doi":"10.1002/adsc.202401268","DOIUrl":"https://doi.org/10.1002/adsc.202401268","url":null,"abstract":"Camphorsultam was utilized for the optical resolution of <i>P</i>‐chiral phosphorous compounds. After chromatographic separation of diastereomeric <i>R</i><sub>P</sub>‐ and <i>S</i><sub>P</sub>‐ phosphonamidate intermediates, subsequent substitution reactions with phenol derivatives yielded <i>P</i>‐chiral phosphonic acid aryl esters with excellent enantioselectivities. In these processes, chiral sulfonamide of camphorsultam demonstrated superior abilities as an optical‐resolving agent and a good leaving group. This method was applied to the synthesis of <i>P</i>‐chiral phosphinic esters, phosphonamidates, and thiophosphonate diesters.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"35 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142718303","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Dibenzoxasilepine Using Ring Expansion Reaction of a Pentacoordinate Silicon Intermediate 利用五配位硅中间体的扩环反应合成二苯并氧西来平
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-27 DOI: 10.1002/adsc.202401125
Keigo WATANABE, Mutsuki Sato, Tsunayoshi Takehara, Kaori ASANO, Tsuyoshi Matsuzaki, Takeyuki Suzuki, Makoto SAKO, Mitsuhiro Arisawa
{"title":"Synthesis of Dibenzoxasilepine Using Ring Expansion Reaction of a Pentacoordinate Silicon Intermediate","authors":"Keigo WATANABE, Mutsuki Sato, Tsunayoshi Takehara, Kaori ASANO, Tsuyoshi Matsuzaki, Takeyuki Suzuki, Makoto SAKO, Mitsuhiro Arisawa","doi":"10.1002/adsc.202401125","DOIUrl":"https://doi.org/10.1002/adsc.202401125","url":null,"abstract":"Dibenzoxasilepine is an important skeleton in both synthetic and medicinal chemistry. Here, we have succeeded in obtaining it in higher yield than the conventional method, elucidating for the first time the rearrangement tendency of the two aromatic rings during the ring expansion reaction on the cyclic pentacoordinate silicon intermediate.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"13 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142718214","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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