Advanced Synthesis & Catalysis最新文献

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Base‐Assisted Orthogonal Synthesis of 4‐Arylisoquinolinediones and Azanaphthoquinones from 2‐Alkynylarylnitriles via Photoactivation by Pyrylium Salt in Visible Light 可见光下吡啶盐光活化2 -炔芳基腈基碱辅助正交合成4 -芳基异喹啉二酮和氮杂醌
IF 4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-29 DOI: 10.1002/adsc.70062
Shruti Rajput , Nidhi Jain
{"title":"Base‐Assisted Orthogonal Synthesis of 4‐Arylisoquinolinediones and Azanaphthoquinones from 2‐Alkynylarylnitriles via Photoactivation by Pyrylium Salt in Visible Light","authors":"Shruti Rajput ,&nbsp;Nidhi Jain","doi":"10.1002/adsc.70062","DOIUrl":"10.1002/adsc.70062","url":null,"abstract":"<div><div>A metal‐free, photooxidative activation of 2‐alkynylarylnitriles in presence of pyrylium salt as a photocatalyst is reported. The 1,2‐diketone intermediate generated in visible light demonstrates base‐assisted orthogonality toward cyclization, furnishing 4‐aryl‐4‐hydroxyisoquinoline‐1,3‐(2<em>H</em>,4<em>H</em>)‐dione and 3‐aryl‐3‐hydroxy‐2,3‐dihydroazanaphthoquinone derivatives. The reaction has a wide substrate scope, good functional group tolerance, uses an organic photocatalyst, and takes place at room temperature. Preliminary biological screening of synthesized molecules reveals their potential as anticancer agents.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 18","pages":"Article e70062"},"PeriodicalIF":4.0,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145196013","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
Iridium‐Catalyzed α‐C–H Alkenylation of Alkylamines with Alkynes Followed by Alkene Isomerization Into Enamines 铱催化α - C-H烷基胺与炔烃的烯基化,随后烯烃异构化成烯胺
IF 4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-29 DOI: 10.1002/adsc.70055
Yuki Takahashi , Kentaro Yamakawa , Takahiro Nishimura
{"title":"Iridium‐Catalyzed α‐C–H Alkenylation of Alkylamines with Alkynes Followed by Alkene Isomerization Into Enamines","authors":"Yuki Takahashi ,&nbsp;Kentaro Yamakawa ,&nbsp;Takahiro Nishimura","doi":"10.1002/adsc.70055","DOIUrl":"10.1002/adsc.70055","url":null,"abstract":"<div><div>The iridium‐catalyzed intermolecular <em>α</em>‐C–H alkenylation of <em>N</em>‐methyl‐2‐aminopyridine derivatives proceeds via alkene isomerization to give the corresponding enamines. The reaction is efficiently catalyzed by a cationic iridium catalyst under mild reaction conditions. The same catalytic system can also be applied to the intramolecular C–H addition to alkynes to give cyclic ketones after hydrolysis of the corresponding enamines.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 18","pages":"Article e70055"},"PeriodicalIF":4.0,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145195985","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
Azabicyclo[1.1.0]butyl‐Substituted Sulfonimidoyl Fluoride: Electrophilic Hub Bridging Late‐Stage Azetidine Incorporation with Sufex Chemistry 氮杂环[1.1.0]丁基取代磺酰酰氟:亲电枢纽桥接晚期氮杂啶结合与硫代化学
IF 4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-29 DOI: 10.1002/adsc.70049
Defne Serbetci , Philipp Natho , Ernesto Mesto , Emanuela Schingaro , Marco Colella , Renzo Luisi
{"title":"Azabicyclo[1.1.0]butyl‐Substituted Sulfonimidoyl Fluoride: Electrophilic Hub Bridging Late‐Stage Azetidine Incorporation with Sufex Chemistry","authors":"Defne Serbetci ,&nbsp;Philipp Natho ,&nbsp;Ernesto Mesto ,&nbsp;Emanuela Schingaro ,&nbsp;Marco Colella ,&nbsp;Renzo Luisi","doi":"10.1002/adsc.70049","DOIUrl":"10.1002/adsc.70049","url":null,"abstract":"<div><div>The development of electrophilic strained small motifs is of increasing importance for chemical biology and drug discovery, enabling precise, late‐stage functionalization and targeted covalent inhibition. In this work, we report the efficient synthesis of a novel azabicyclo[1.1.0]butyl‐substituted sulfonimidoyl fluoride, a bench‐stable electrophilic hub combining strain‐release reactivity and SuFEx chemistry. The dual reactivity of this motif was demonstrated through selective ABB ring‐opening reactions, and SuFEx‐mediated ligations with diverse nucleophiles, including pharmaceutically relevant derivatives. Further derivatization of the resulting sulfonimidates and sulfonimidamides showcased the synthetic versatility of this system. These findings open avenues for the development of modular, multifunctional platforms in drug discovery.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 18","pages":"Article e70049"},"PeriodicalIF":4.0,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145196014","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/BINAP/Peroxide‐Enabled Relay Multicomponent Reactions Pd/BINAP/过氧化氢激活继电器多组分反应
IF 4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-29 DOI: 10.1002/adsc.70050
Yan‐Nian Pan , Cheng‐Kai Yuan , Zhen‐Chun Li , Yi Lu
{"title":"Pd/BINAP/Peroxide‐Enabled Relay Multicomponent Reactions","authors":"Yan‐Nian Pan ,&nbsp;Cheng‐Kai Yuan ,&nbsp;Zhen‐Chun Li ,&nbsp;Yi Lu","doi":"10.1002/adsc.70050","DOIUrl":"10.1002/adsc.70050","url":null,"abstract":"<div><div>In recent years, multicomponent reactions have attracted considerable attention due to their efficiency in constructing complex molecules from simple starting materials. Herein, we report a BINAP/peroxide‐controlled Pd‐catalyzed multicomponent reaction involving readily accessible indoles, diazo compounds, and allylic electrophiles, enabling the efficient synthesis of structurally diverse N‐functionalized indoles bearing aza‐quaternary carbon centers, which are prevalent in bioactive molecules and pharmaceuticals. This approach exhibits broad functional group tolerance and excellent regioselectivity for N–H sites, especially applicable to unsubstituted indoles. We have further demonstrated the synthetic utility of the resulting products through various derivatizations, including a concise four‐step synthesis of a mineralocorticoid receptor antagonist to treat aldosterone‐mediated diseases. Mechanistic experiments indicated that this reaction was enabled by a relay catalysis based on Pd<sup>II</sup>/Pd<sup>II</sup> non‐redox and Pd<sup>0</sup>/Pd<sup>II</sup> redox catalytic cycles, which was found to facilitate the activation of carbene and allylic substrates, respectively. The addition of peroxide was found to suppress the premature formation of [<strong>Pd</strong><sup><strong>0</strong></sup><strong>(BINAP)</strong>] species and keep palladium in the [<strong>Pd</strong><sup><strong>II</strong></sup><strong>(BINAP)(OAc)</strong><sub><strong>2</strong></sub>] form at the beginning of the reaction, thereby avoiding the formation of undesired indole allylation by‐products and significantly increasing the overall yields of the target products.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 18","pages":"Article e70050"},"PeriodicalIF":4.0,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145196017","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‐Catalyzed Three‐Component Silylamidation of Terminal Alkynes 铜催化末端炔的三组分硅基酰胺化
IF 4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-29 DOI: 10.1002/adsc.70028
Jing Ren , Xiangxiang Kong , Ning Wang , Jinlong Li , Xinyu Long , Kaizhi Li
{"title":"Copper‐Catalyzed Three‐Component Silylamidation of Terminal Alkynes","authors":"Jing Ren ,&nbsp;Xiangxiang Kong ,&nbsp;Ning Wang ,&nbsp;Jinlong Li ,&nbsp;Xinyu Long ,&nbsp;Kaizhi Li","doi":"10.1002/adsc.70028","DOIUrl":"10.1002/adsc.70028","url":null,"abstract":"<div><div>Herein, the successful development of a copper‐catalyzed three‐component silylamidation of alkynes, involving hydrosilanes and picolinamides, is described. This methodology provides an innovative and efficient route for the production of diverse silylated enamides, distinguished by its broad substrate compatibility and exceptional functional group tolerance. The synthetic versatility of this reaction is exemplified by its application in the late‐stage modification of substrates featuring complex motifs. Moreover, detailed studies on the reaction mechanism have been conducted through various mechanistic experiments.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 18","pages":"Article e70028"},"PeriodicalIF":4.0,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145196012","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
Electrocatalytic Dehydrogenative Lactonization of Benzylic Alcohols: A Sustainable Access to Phthalides via N-hydroxyphthalimide Mediation 苯甲酸醇的电催化脱氢内酯化:通过n -羟基邻苯二甲酸亚胺介导的可持续获取邻苯二甲酸酯
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-28 DOI: 10.1002/adsc.70138
Pietro Ronco, Antonia Simi, Enrico Lunghi, Emanuele Casali, Giovanni Lenardon, Alessio Porta, Giuseppe Zanoni
{"title":"Electrocatalytic Dehydrogenative Lactonization of Benzylic Alcohols: A Sustainable Access to Phthalides via N-hydroxyphthalimide Mediation","authors":"Pietro Ronco, Antonia Simi, Enrico Lunghi, Emanuele Casali, Giovanni Lenardon, Alessio Porta, Giuseppe Zanoni","doi":"10.1002/adsc.70138","DOIUrl":"https://doi.org/10.1002/adsc.70138","url":null,"abstract":"A sustainable and efficient electrochemical method for the direct oxidative lactonization of benzylic alcohols, enabling rapid access to isobenzofuran-1(3H)-ones (phthalides) is presented. This electrocatalytic transformation leverages <i>N</i>-hydroxyphthalimide as a redox mediator under mild, metal-free conditions, offering an environmentally friendly alternative to traditional oxidation protocols. The method demonstrates broad substrate scope and delivers phthalide derivatives consistently in good to excellent yields. Mechanistic studies, combining cyclic voltammetry and density functional theory calculations, support a radical-mediated hydrogen atom transfer mechanism driven by phthalimide-<i>N</i>-oxyl radicals. Importantly, the utility of the protocol extends beyond model substrates: it is successfully applied to the synthesis of pharmaceutically relevant compounds, including talopram and a key intermediate for a neuropeptide Y5 receptor antagonist. Overall, this work underscores the power of electrosynthesis in modern organic chemistry, merging green chemistry principles with synthetic efficiency.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"4 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145182982","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
Ortho-Functionalized Diaryliodonium Salts: Synthesis and Reactivity 邻位官能化二芳基碘鎓盐:合成与反应性
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-28 DOI: 10.1002/adsc.70135
Lifeng Chu, Limin Wang, Jianwei Han
{"title":"\u0000Ortho-Functionalized Diaryliodonium Salts: Synthesis and Reactivity","authors":"Lifeng Chu, Limin Wang, Jianwei Han","doi":"10.1002/adsc.70135","DOIUrl":"https://doi.org/10.1002/adsc.70135","url":null,"abstract":"Hypervalent iodine reagents have attracted considerable attention in modern organic synthesis due to their low toxicity and versatile reactivity. Among them, <i>ortho</i>-functionalized diaryliodonium salts represent an important subclass, distinguished by their unique structural characteristics and reactivity. This review summarizes recent advances in the development of <i>ortho</i>-functionalized diaryliodonium reagents, with particular emphasis on the role of <i>ortho</i>-substituents as leaving groups or participanting moieties in reactions. Newly developed transformations are discussed alongside their mechanisms, highlighting the intramolecular interactions with the iodine(III) center.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"4 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145182981","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
Gold-Catalyzed Conia-Ene Reaction of Malonate Derivatives Bearing An Alkyne Moiety by Using a Phosphine–Borane Ligand 用膦-硼烷配体催化含炔丙二酸酯衍生物的con_2 - ene反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-27 DOI: 10.1002/adsc.70064
Gen Onodera, Hiroki Shimizu, Rintaro Kuwahara, Kaishi Kawasaki, Norbert Krause, Tsutomu Fukuda, Masanari Kimura
{"title":"Gold-Catalyzed Conia-Ene Reaction of Malonate Derivatives Bearing An Alkyne Moiety by Using a Phosphine–Borane Ligand","authors":"Gen Onodera, Hiroki Shimizu, Rintaro Kuwahara, Kaishi Kawasaki, Norbert Krause, Tsutomu Fukuda, Masanari Kimura","doi":"10.1002/adsc.70064","DOIUrl":"https://doi.org/10.1002/adsc.70064","url":null,"abstract":"A gold-catalyzed Conia-ene reaction of malonate derivatives is developed by using a phosphine–borane ligand. This catalyst system can be applicable not only for 5-<i>exo-dig</i>-mode cyclization reactions but also for 5-<i>endo-dig</i>-mode cyclizations. A variety of 2-(4-pentynyl)malonates and 2-(3-butynyl)malonates afford the corresponding cyclic compounds in moderate to high yields. The boryl enolate might be formed in situ and attacks intramolecularly an alkyne moiety, activated by a gold catalyst, is considered.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"4 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145153756","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
N-Containing Carbon Materials in Metal-Free and Non-Noble Metal Liquid Phase Heterogenous Catalysis 含氮碳材料在无金属和非贵金属液相多相催化中的应用
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-27 DOI: 10.1002/adsc.70134
Fulvio Varamo, Anna Katharina Beine
{"title":"N-Containing Carbon Materials in Metal-Free and Non-Noble Metal Liquid Phase Heterogenous Catalysis","authors":"Fulvio Varamo, Anna Katharina Beine","doi":"10.1002/adsc.70134","DOIUrl":"https://doi.org/10.1002/adsc.70134","url":null,"abstract":"Non-noble metal and metal-free catalysts can be of great benefit for the development of economically and environmentally sustainable chemical processes. In this context, N-containing carbon materials serve both as effective catalyst supports and standalone catalysts, offering enhanced stability by mitigating deactivation mechanisms such as metal leaching and sintering. The review is primarily organized by non-noble metal, systematically covering each case in which their use as an active phase on N-containing carbon materials has been reported in literature. In parallel, cross-cutting aspects are examined throughout, including the role of different N-functionalities (graphitic, pyridinic, pyrrolic, and pyridinic-N-oxide) in active-phase stabilization mechanisms. Structurally diverse carbon materials—such as amorphous carbon, carbon nanotubes, carbon spheres, carbon nanofibers, and graphene—are also considered. Furthermore, the influence of preparation methods, including template-free, hard-templating and soft-templating techniques, is analyzed with emphasis on their role in tuning textural properties. Despite significant progress, uncertainties remain regarding the precise stabilization mechanisms and the relative contributions of different N-functionalities to catalytic activity and surface acid–base properties. Addressing these knowledge gaps will be essential for optimization of N-containing carbon materials and to drive the transition towards greener and more sustainable catalytic technologies.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"26 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145153757","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
Light Mediated Sulfonylation/C–H Activation/Annulation of Benzimidazoles Derivatives Catalyzed by Diarylmethylium Tetrafluoroborate Salts: An Experimental and Computational Study 四氟硼酸二芳基甲基盐催化苯并咪唑衍生物的光介导磺化/碳氢活化/环化:实验和计算研究
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-27 DOI: 10.1002/adsc.70086
Polyssena Renzi, Davide Cerrina, Emanuele Azzi, Giovanni Ghigo, Annamaria Deagostino
{"title":"Light Mediated Sulfonylation/C–H Activation/Annulation of Benzimidazoles Derivatives Catalyzed by Diarylmethylium Tetrafluoroborate Salts: An Experimental and Computational Study","authors":"Polyssena Renzi, Davide Cerrina, Emanuele Azzi, Giovanni Ghigo, Annamaria Deagostino","doi":"10.1002/adsc.70086","DOIUrl":"https://doi.org/10.1002/adsc.70086","url":null,"abstract":"In this article, diarylmethylium tetrafluoroborates are exploited as catalysts in a visible light promoted domino sulfonylation/C–H activation/annulation of <jats:italic>N</jats:italic>‐alkynylbenzimidazoles producing polycyclic sulfonyl‐benzimidazoles. Annulated benzimidazoles are important structures in pharmaceutical research and drug discovery known for their biological and medicinal properties. More than 20 polycyclic sulfonyl‐benzimidazoles, including azepines, are obtained in good to excellent yields, in mild and metal free conditions. A mechanism proposal, based on both experimental and computational studies, establishes the role of the photoactive ion couple formed between the cation catalyst and the sulfinate in producing the key sulfonyl radical. The latter adds to the triple bond thus promoting a domino process in which the acid additive has a fundamental role in the hydrogen transfer. In addition, an acid‐catalyzed proton‐coupled electron‐transfer closes the catalytic cycle regenerating the diarylcarbenium salt thus yielding the desired product.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"65 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145181128","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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