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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
Regioselective Palladaelectro‐catalyzed Chlorination of Arenes in an Undivided Cell 非分裂电池中帕拉代电催化的烯类区域选择性氯化反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-27 DOI: 10.1002/adsc.202401298
Sudipta Ponra, Ruzal Sitdikov, Alyssio Calis, Oscar Verho
{"title":"Regioselective Palladaelectro‐catalyzed Chlorination of Arenes in an Undivided Cell","authors":"Sudipta Ponra, Ruzal Sitdikov, Alyssio Calis, Oscar Verho","doi":"10.1002/adsc.202401298","DOIUrl":"https://doi.org/10.1002/adsc.202401298","url":null,"abstract":"Chloroarenes constitute fundamental building blocks in organic synthesis and are widely applied in the synthesis of bioactive compounds, fine chemicals, materials, natural products and pharmaceuticals. Electrochemical chlorination has been recognized as a promising synthetic method for accessing chloroarenes, but it has proved challenging to achieve in practice as shown by the limited number of existing protocols. Herein, we report on a highly general electrocatalytic strategy for the regioselective chlorination of various substituted heteroaryl scaffolds in an undivided cell setup, using ethyl chloroformate as the chlorine source. This strategy offers several practical advantages over existing methodologies, including an operationally simple experimental setup, exceptional functional group tolerance, and the possibility to form either the mono‐ or bis‐chlorinated products in high selectivity depending on the choice of catalyst loading, electric current and ethyl chloroformate equivalents. The practicality and selectivity of the protocol were demonstrated by the successful chlorination of an array of densely‐substituted arene frameworks as well as by the synthesis of chlorinated bioactive molecules.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"10 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142718367","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
Electrochemical Dual Trifluoromethylation/Cyclization of 2-Aryl-N-acryloyl Indoles Enabling Assembly of Indole[2,1-a]isoquinolines 电化学双三氟甲基化/环化 2-芳基-N-丙烯酰基吲哚促成吲哚并[2,1-a]异喹啉的组装
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-27 DOI: 10.1002/adsc.202401225
Haibo Mei, Yucheng Zhang, Jiang Liu, Jorge Escorihuela, Lorand Kiss, Jianlin Han
{"title":"Electrochemical Dual Trifluoromethylation/Cyclization of 2-Aryl-N-acryloyl Indoles Enabling Assembly of Indole[2,1-a]isoquinolines","authors":"Haibo Mei, Yucheng Zhang, Jiang Liu, Jorge Escorihuela, Lorand Kiss, Jianlin Han","doi":"10.1002/adsc.202401225","DOIUrl":"https://doi.org/10.1002/adsc.202401225","url":null,"abstract":"An electrochemical cascade radical cyclization of 2-aryl-N-acryloyl indoles with sodium trifluoromethanesulfinate as a coupling partner has been explored, which afforded the unexpected bis-trifluoromethylated indole[2,1-a]isoquinolines as products. Experimental results and DFT calculations disclose that this reaction involves trifluoromethylation-triggered cyclization and the second trifluoromethylation as the key steps. This strategy does not need any transition-metal catalysts or oxidants with a readily available trifluoromethylating reagent enabling facile synthesis of bis-trifluoromethylated indole-fused tricycles.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"93 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142735602","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
3,4‐Dicyano‐2,5,6‐Trifluorophenyl Glycosides as Electron‐Deficient Fluoroarene Glycosyl Donors for Chemical Glycosylation 3,4-二氰基-2,5,6-三氟苯基苷作为用于化学糖基化的缺电子芴糖基捐赠者
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-27 DOI: 10.1002/adsc.202401196
Ariza Khanam, Ashwani Tiwari, Mohammad Ovais, Mohan Lal, Pintu Kumar Mandal
{"title":"3,4‐Dicyano‐2,5,6‐Trifluorophenyl Glycosides as Electron‐Deficient Fluoroarene Glycosyl Donors for Chemical Glycosylation","authors":"Ariza Khanam, Ashwani Tiwari, Mohammad Ovais, Mohan Lal, Pintu Kumar Mandal","doi":"10.1002/adsc.202401196","DOIUrl":"https://doi.org/10.1002/adsc.202401196","url":null,"abstract":"Here, we present 3,4‐dicyano‐2,5,6‐trifluorophenyl glycosides as bench‐stable, and reactive electron‐deficient fluoroarene based glycosyl donors that can be prepared in one‐step and be activated with catalytic amounts of TMSOTf. The glycosylation reaction conditions show tolerance towards acid/base sensitive protecting groups and have a different substrate scope with 68‐89% yields. The electron‐deficient fluoroarene‐containing glycosyl donor enables the construction of O‐ and C‐glycosides using both free alcohols and silylated alcohols, as well as C‐ nucleophiles as acceptors.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"46 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142718392","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
From gem-Dichlorocyclobutenones to Cyclobutenols: Unveiling a Ruthenium-Catalyzed Allylic Reduction-Asymmetric Transfer Hydrogenation Cascade 从二氯环丁烯酮到环丁烯醇：揭示钌催化的烯丙基还原-不对称转移氢化级联反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-27 DOI: 10.1002/adsc.202401406
Christophe MEYER, Olivier Charron, Marharyta Kosiuha, Virginie Ratovelomanana-Vidal, Phannarath Phansavath, Geoffrey Gontard
{"title":"From gem-Dichlorocyclobutenones to Cyclobutenols: Unveiling a Ruthenium-Catalyzed Allylic Reduction-Asymmetric Transfer Hydrogenation Cascade","authors":"Christophe MEYER, Olivier Charron, Marharyta Kosiuha, Virginie Ratovelomanana-Vidal, Phannarath Phansavath, Geoffrey Gontard","doi":"10.1002/adsc.202401406","DOIUrl":"https://doi.org/10.1002/adsc.202401406","url":null,"abstract":"Cyclobutenones constitute an appealing class of substrates in catalytic asymmetric transformations leading to diversely substituted enantioenriched four-membered carbocycles, which are eliciting a growing interest in medicinal chemistry. Whilst several synthetically useful enantioselective conjugate addition reactions have been reported, the catalytic enantioselective reduction of the carbonyl group of simple cyclobutenones remains an elusive transformation. Herein, we disclose the discovery of a novel allylic reduction-asymmetric transfer hydrogenation cascade, catalyzed by a Noyori-Ikariya ruthenium complex, from readily available gem-dichlorocyclobutenones, leading to 2-chlorocyclobutenols with high optical purities, which can be engaged in postfunctionalization reactions enabling access to substituted four-membered rings.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"9 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142735823","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
Base-promoted [4+3] Cycloadditions of N-Thioacylimines with α-chlorohydroxamates: Construction of 1,3,5-Thiadiazepin-6(7H)-one Derivatives
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-27 DOI: 10.1002/adsc.202401193
Yu-Di Liu, Yu-Heng Shao, Zhao-Lin He, Gang Wang
{"title":"Base-promoted [4+3] Cycloadditions of N-Thioacylimines with α-chlorohydroxamates: Construction of 1,3,5-Thiadiazepin-6(7H)-one Derivatives","authors":"Yu-Di Liu, Yu-Heng Shao, Zhao-Lin He, Gang Wang","doi":"10.1002/adsc.202401193","DOIUrl":"https://doi.org/10.1002/adsc.202401193","url":null,"abstract":"A metal-free base-promoted [4+3] cycloaddition reaction of N-thioacyl imines in situ generated from α-amido sulfones with α-chlorohydroxamates is described. The reaction facilitates the straightforward synthesis of 1,3,5-thiadiazepin-6(7H)-one derivatives in 44~90% yields. Moreover, a gram-scale reaction and product transformation were conducted, which further increased the diversity of products.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"25 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142753428","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
Base-Mediated Sequential Annulation Reaction of Conjugated Dienes and Crotonate-derived Sulfur Ylides：Effective Synthesis of Bicyclo[4.1.0]heptenes 碱介导的共轭二烯与巴豆酸盐衍生硫酰的序贯环化反应：双环[4.1.0]庚烯的有效合成
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-25 DOI: 10.1002/adsc.202401273
Zhenjie Gan, Jingran Sun, Zhangyun Huang, Zhenjue Cai, Yue Wang, Er-Qing Li
{"title":"Base-Mediated Sequential Annulation Reaction of Conjugated Dienes and Crotonate-derived Sulfur Ylides：Effective Synthesis of Bicyclo[4.1.0]heptenes","authors":"Zhenjie Gan, Jingran Sun, Zhangyun Huang, Zhenjue Cai, Yue Wang, Er-Qing Li","doi":"10.1002/adsc.202401273","DOIUrl":"https://doi.org/10.1002/adsc.202401273","url":null,"abstract":"Herein we present a method for base-mediated sequential annulation reaction of conjugated dienes. The method offers an efficient pathway for the effective construction of bicyclo[4.1.0]heptenes. Notable features of this approach include good yields, remarkable stereoselectivity, as well as a broad substrate scope and significant step efficiency. In addition, the reaction could be effectively scaled up to a gram scale under standard condition.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"77 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142712997","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
Modular Chiral Bithiophene-2NO Ligands: Synthesis and Application in Asymmetric Palladium(II)-catalysed Friedel-Crafts Alkylation 模块化手性噻吩-2NO 配体：不对称钯（II）催化的 Friedel-Crafts 烷基化反应中的合成与应用
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-25 DOI: 10.1002/adsc.202401348
Xian-Qiao Zhu, Wu-Wu Li, Lin-Lu Liu, Wen-Jing Zhang, Ke-Lan Xu, Li-Jun Peng, Min Zhang, Xiong-Li Liu
{"title":"Modular Chiral Bithiophene-2NO Ligands: Synthesis and Application in Asymmetric Palladium(II)-catalysed Friedel-Crafts Alkylation","authors":"Xian-Qiao Zhu, Wu-Wu Li, Lin-Lu Liu, Wen-Jing Zhang, Ke-Lan Xu, Li-Jun Peng, Min Zhang, Xiong-Li Liu","doi":"10.1002/adsc.202401348","DOIUrl":"https://doi.org/10.1002/adsc.202401348","url":null,"abstract":"The development of privileged thiophene-type ligand remains highly desirable, owing to the high coordination ability of sulfur atom to most of the soft metals. Herein, a new class of C2-symmetric rigid chiral tertiary amine-derived dioxide ligands with a coordinating bithiophene bridge was developed in a convenient synthetic route with 25-62% overall yields. The bithiophene-2NO-palladium(II) catalyst system was generated in situ and found to be highly capable catalyst in the asymmetric Friedel-Crafts alkylation of indoles. Excellent yields (up to 92%) and high enantioselectivities (up to >99% ee) are obtained for a wide range of substrates under mild conditions. Control experiments and DFT calculations revealed the origins of the enantioselectivity. This represented the first example of chiral thiophene ligands coordinating with soft metal Pd(II) in the asymmetric Friedel-Crafts alkylation. Experiments revealed that the counteranion is involved in the stereoselectivity-determining step in this soft palladium(II) catalysis, and the additional NO and thiophene in ligands can act as the second chelation site and thus reduce the amount of free metal ions for suppressing background reaction in the catalytic system.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"20 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142713064","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
Ruthenium‐Catalyzed Regioselective Tandem Cycloisomerization/Diels‐Alder Reaction of 1,7‐Enynes 钌催化的 1,7-炔的区域选择性串联环异构化/Diels-Alder 反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-21 DOI: 10.1002/adsc.202401157
Ravichandran Logeswaran, Masilamani Jeganmohan
{"title":"Ruthenium‐Catalyzed Regioselective Tandem Cycloisomerization/Diels‐Alder Reaction of 1,7‐Enynes","authors":"Ravichandran Logeswaran, Masilamani Jeganmohan","doi":"10.1002/adsc.202401157","DOIUrl":"https://doi.org/10.1002/adsc.202401157","url":null,"abstract":"A ruthenium‐catalyzed methodology for regioselective cycloisomerization and tandem Diels‐Alder reactions of 1,7‐enynes has been described, enabling the versatile synthesis of diverse polycyclic heterocycles with four stereocenters. This stereoselective protocol demonstrates excellent compatibility with various substituted enynes and alkenes, yielding products in 46–90% yields while tolerating a wide range of functional groups, including esters, ketones, and halides. Notably, the reaction with naphthoquinones retains the moiety in the final product, which acts as essential core structures in various natural products and bioactive compounds.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"253 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142679092","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 Allylic Substitution Using Nucleophilic Amines: Access to Functionalized Mono‐ and Bis‐N‐Allyl Synthons 使用亲核胺的钯催化烯丙基取代反应：获得功能化的单-和双-N-烯丙基合成物
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-19 DOI: 10.1002/adsc.202400685
Fengyun Gao , Debasish Ghorai , Jordi Benet‐Buchholz , Arjan W. Kleij
{"title":"Pd‐Catalyzed Allylic Substitution Using Nucleophilic Amines: Access to Functionalized Mono‐ and Bis‐N‐Allyl Synthons","authors":"Fengyun Gao ,&nbsp;Debasish Ghorai ,&nbsp;Jordi Benet‐Buchholz ,&nbsp;Arjan W. Kleij","doi":"10.1002/adsc.202400685","DOIUrl":"10.1002/adsc.202400685","url":null,"abstract":"<div><div>We here report a catalytic strategy to enable the decarboxylative allylic amination of vinyl cyclic carbonates using various aliphatic and nucleophilic amines. The use of a protic medium and chelating diphosphine ligands are the main drivers towards chemoselective allylic amine formation, thereby minimizing undesired ligand‐driven complex speciation and aminolysis of the involved substrate. This improved approach amplifies the repertoire of allylic amine synthons that can be prepared from a variety of substrate combinations.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4709-4714"},"PeriodicalIF":4.4,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202400685","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141910558","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
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