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PTC in the Polyenolate‐Mediated [10+2]‐Cycloaddition for the Synthesis of α,α‐Disubstituted Amino Acid Precursors PTC 在聚烯酸酯介导的 [10+2]- 环加成反应中用于合成 α、α- 二取代氨基酸前体
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-15 DOI: 10.1002/adsc.202400792
Joanna Dybowska , Artur Przydacz , Anna Skrzyńska , Łukasz Albrecht
{"title":"PTC in the Polyenolate‐Mediated [10+2]‐Cycloaddition for the Synthesis of α,α‐Disubstituted Amino Acid Precursors","authors":"Joanna Dybowska ,&nbsp;Artur Przydacz ,&nbsp;Anna Skrzyńska ,&nbsp;Łukasz Albrecht","doi":"10.1002/adsc.202400792","DOIUrl":"10.1002/adsc.202400792","url":null,"abstract":"<div><div>The manuscript describes a formal [10+2] higher‐order cycloaddition between 2‐arylideneindan‐1‐ones and α‐alkylidene azlactones as higherene precursors and higherenofiles respectively. The reaction is realized under Brønsted‐base catalysis utilizing the phase transfer catalysis approach. The key intermediate is an isobenzofulvene‐derived polyenolate which acts as a 10‐electron component in the higher‐order cycloaddition. By using this strategy, a series of structurally diverse compounds containing a polycyclic hydrocarbon scaffold was prepared in 79–99% yields. In addition, the potential of the obtained [10+2]‐cycloadducts has been confirmed by transformations, including the synthesis of a highly‐valuable α,α‐disubstituted <em>N</em>‐protected α‐aminoester.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 8","pages":"Article e202400792"},"PeriodicalIF":4.4,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102000","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 Tetrahydroisoquinolin‐4‐Ones via Rh(II)‐Catalyzed One‐Pot Reaction of Aldehyde‐Tethered N‐Sulfonyl‐1,2,3‐Triazoles with Indoles Rh（II）催化醛系n-磺酰基-1,2,3-三唑与吲哚的一锅反应合成四氢异喹啉-4-酮
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-15 DOI: 10.1002/adsc.202401584
Hui Meng , Zehua Wang , Ze‐Feng Xu , Chuan‐Ying Li
{"title":"Synthesis of Tetrahydroisoquinolin‐4‐Ones via Rh(II)‐Catalyzed One‐Pot Reaction of Aldehyde‐Tethered N‐Sulfonyl‐1,2,3‐Triazoles with Indoles","authors":"Hui Meng ,&nbsp;Zehua Wang ,&nbsp;Ze‐Feng Xu ,&nbsp;Chuan‐Ying Li","doi":"10.1002/adsc.202401584","DOIUrl":"10.1002/adsc.202401584","url":null,"abstract":"<div><div>A rhodium (II)‐catalyzed transannulation reaction between aldehyde‐tethered <em>N</em>‐sulfonyl‐1,2,3‐triazoles and indoles was reported, which resulted in the formation of functionalized tetrahydroisoquinolin‐4‐ones. This reaction is notable for its broad substrate scope, including a variety of <em>N</em>‐sulfonyl‐1,2,3‐triazoles and different indoles. The addition of a protonic acid is essential for improving the yield of the desired tetrahydroisoquinolin‐4‐one products.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 8","pages":"Article e202401584"},"PeriodicalIF":4.4,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143538664","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
Homogeneous Copper-Catalyzed Cycloisomerization Reaction of Allenynes: Rapid Access to Functionalized Pyrroles 铜催化的均相烯炔环异构化反应：快速获得功能化吡咯
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-14 DOI: 10.1002/adsc.202500303
Kua-Fei Wei, Xiu-Hong Zhu, Guang-Xin Ru, Wen-Bo Shen
{"title":"Homogeneous Copper-Catalyzed Cycloisomerization Reaction of Allenynes: Rapid Access to Functionalized Pyrroles","authors":"Kua-Fei Wei, Xiu-Hong Zhu, Guang-Xin Ru, Wen-Bo Shen","doi":"10.1002/adsc.202500303","DOIUrl":"https://doi.org/10.1002/adsc.202500303","url":null,"abstract":"Homogeneous transition-metal-catalyzed alkyne cascade cyclization reaction has attracted much attentions over the past decades. However, the relevant homogeneous transition-metal-catalyzed cyclization of allenynes has seldom been explored probably due to noticeable chemo-, regio-, and stereoselectivity. Described herein is an efficient homogeneous copper-catalyzed cycloisomerization reaction of allenynes, thus leading to a practical and atom-economic access to an array of valuable functionalized pyrroles by formal [3 + 2] cycloaddition via Cu-containing all-carbon 1,4-dipoles.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"7 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143832189","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
Pot-Economical Synthesis of Fluorinated Pyrrolizinone Derivatives 氟化吡咯烷酮衍生物的锅内经济合成
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-14 DOI: 10.1002/adsc.202500209
Lidia Prieto, Marcos Escolano, Daniel Gaviña, Luis Paredes-Soler, Santiago Díaz Oltra, Maria Sanchez-Rosello, Carlos del Pozo
{"title":"Pot-Economical Synthesis of Fluorinated Pyrrolizinone Derivatives","authors":"Lidia Prieto, Marcos Escolano, Daniel Gaviña, Luis Paredes-Soler, Santiago Díaz Oltra, Maria Sanchez-Rosello, Carlos del Pozo","doi":"10.1002/adsc.202500209","DOIUrl":"https://doi.org/10.1002/adsc.202500209","url":null,"abstract":"A new family of fluorinated dihydropyrrolizinones has been synthesized starting from fluorinated enamino amides and aliphatic conjugated ketones. The reaction comprises a cross metathesis reaction followed by a tandem cycloaromatization/ enamine hydrolysis/ intramolecular Friedel-Crafts alkylation sequence. This pot-economical process takes place in good yields (35-67%), taking into account that it consists of four consecutive reactions. Aromatic enones are also good partners for this protocol although, in this case, the cross metathesis reaction has to be performed in a separated step.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"76 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143832188","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
Illuminating the Path of Rearrangement: Visible Light-Driven Pd-Catalyzed Substituted Olefins Synthesis 照亮重排之路：可见光驱动pd催化取代烯烃合成
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-14 DOI: 10.1002/adsc.202500161
jenifer Sharshonov, Valentin Duchemann, Yuqian Sun, Christine Tran, Philippe Belmont, Abdallah HAMZE, Diana Lamaa, Etienne BRACHET
{"title":"Illuminating the Path of Rearrangement: Visible Light-Driven Pd-Catalyzed Substituted Olefins Synthesis","authors":"jenifer Sharshonov, Valentin Duchemann, Yuqian Sun, Christine Tran, Philippe Belmont, Abdallah HAMZE, Diana Lamaa, Etienne BRACHET","doi":"10.1002/adsc.202500161","DOIUrl":"https://doi.org/10.1002/adsc.202500161","url":null,"abstract":"Pd-catalyzed reactions are among the most straightforward and efficient methods to proficiently build Csp2-Csp2 bonds. Nevertheless, thermal activation remains mandatory in most cases, which may decrease the compatibility with sensitive functional groups. In this context, improvements of conventional strategies must be an important source of research in order to enhance the applicability of such methods for building complex scaffolds. In this work, we contribute to this aim by implying visible-light as the sole energy source in a Pd-catalyzed rearrangement reaction involving N-tosylhydrazones and aryl halides. These mild reaction conditions efficiently allow oxidative addition, aryl migration and β-hydride elimination at room temperature, allowing the construction of various 1,1’ disubstituted olefins.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"23 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143832190","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 Polysubstitued Naphthalenes via Metal-free Borylative Cyclization of o-Alkynylstyrenes 邻炔基苯乙烯无金属硼化环化合成多取代萘
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-14 DOI: 10.1002/adsc.202500244
Marcos Humanes, Manuel Ángel Fernández-Rodríguez, Patricia García-García
{"title":"Synthesis of Polysubstitued Naphthalenes via Metal-free Borylative Cyclization of o-Alkynylstyrenes","authors":"Marcos Humanes, Manuel Ángel Fernández-Rodríguez, Patricia García-García","doi":"10.1002/adsc.202500244","DOIUrl":"https://doi.org/10.1002/adsc.202500244","url":null,"abstract":"A selective, metal-free method for the synthesis of boron-functionalized polysubstituted naphthalenes via BCl₃-mediated cyclization of α-substituted o-alkynylstyrenes is described. The reaction exhibits broad substrate scope, tolerating various groups such as ethers, sulfides and halogens, and delivers high yields under mild conditions, even at gram scale. The resulting Bpin-functionalized naphthalenes serve as versatile building blocks, facilitating further transformations of the C–B bond into C–H, C–C, C–I, C–O, and C–N bonds, thereby increasing molecular complexity and enabling the design of more functionalized products.\u0000Notably, this sustainable and straightforward protocol selectively introduces the Bpin group at the sterically hindered α-carbon of the naphthalene framework, complementing C–H borylations of the naphthalene core, that preferentially occur at the β-position. As a result, the developed approach significantly broadens the accessibility of B-functionalized naphthalene derivatives for synthetic and application-oriented purposes.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"24 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143832187","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
Harnessing Nitroarenes in Streamlined Synthesis of 4‐Quinolones via Reductive C−N Coupling 利用硝基芳烃通过还原C - N偶联流线型合成4 -喹诺酮类药物
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-11 DOI: 10.1002/adsc.202500393
Ni Dong, Xiao-Tian Zhang, Qin Tang, Jia-Xin Qian, Qi-Qi Luo, Long Cheng, Tian Cao, Xiang-Wei Liu
{"title":"Harnessing Nitroarenes in Streamlined Synthesis of 4‐Quinolones via Reductive C−N Coupling","authors":"Ni Dong, Xiao-Tian Zhang, Qin Tang, Jia-Xin Qian, Qi-Qi Luo, Long Cheng, Tian Cao, Xiang-Wei Liu","doi":"10.1002/adsc.202500393","DOIUrl":"https://doi.org/10.1002/adsc.202500393","url":null,"abstract":"The synthesis of quinolones is a key technology for the preparation of active pharmaceutical ingredients. Herein we present a step‐economical methodology for streamlined synthesis of 4‐quinolones from a tandem process involving a reduction of nitroarenes, an aza‐Michael addition and an intramolecular Buchwald‐Hartwig amination. This strategy uses synthetically upstream nitroarenes as viable aniline surrogates and B2pin2 as an enabling organic reductant, producing a wide range of 4‐quinolones bearing different functional groups in a step‐economical fashion. The potential value of this protocol is highlighted by late‐stage installation of 4‐quinolone moiety onto bioactive compounds.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"60 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143818943","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
Regio‐, Stereoselective, Aerobic and Metal‐Free Synthesis of Z‐Vinyl Sulfides: One‐pot Hydroiodination of Internal Alkynes and in situ Sulfenylations Z -乙烯基硫化物的区域、立体选择性、有氧和无金属合成：内炔的一锅加氢碘化和原位磺化
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-11 DOI: 10.1002/adsc.202500388
Gloria Morís-Menéndez, Sergio E García-Garrido, Pablo García-Álvarez, Alejandro Presa Soto, Nicolás Ríos-Lombardía, Joaquín García-Álvarez
{"title":"Regio‐, Stereoselective, Aerobic and Metal‐Free Synthesis of Z‐Vinyl Sulfides: One‐pot Hydroiodination of Internal Alkynes and in situ Sulfenylations","authors":"Gloria Morís-Menéndez, Sergio E García-Garrido, Pablo García-Álvarez, Alejandro Presa Soto, Nicolás Ríos-Lombardía, Joaquín García-Álvarez","doi":"10.1002/adsc.202500388","DOIUrl":"https://doi.org/10.1002/adsc.202500388","url":null,"abstract":"A novel, metal‐free, air‐ and moisture‐compatible one‐pot tandem protocol for the regio‐ and stereoselective synthesis of Z‐vinyl sulfides (achieving yields up to 99%), is reported. This straightforward and efficient process combines the selective hydroiodination of internal alkynes, promoted by the eutectic mixture choline iodide (ChI)/p‐TsOH (1:1) under mild, bench‐type conditions (without the need for toxic molecular HI), with a subsequent sulfenylation step of the in situ‐generated vinyl iodides. This final step is compatible with aromatic, heteroaromatic and aliphatic thiols. Notably, the methodology addresses a longstanding challenge by enabling the selective formation of Markovnikov products with Z‐configuration in the thiolation of secondary propiolamides. It also avoids volatile organic solvents and is easily scalable to gram quantities, offering significant advantages for synthetic applications.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"25 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143819399","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
High‐Performance and Recyclable Multisite Catalytic System for CO₂ Fixation Using Crown Ether‐Linked Schiff Base and Alkali Halides 利用冠醚连接的希夫碱和碱卤化物催化固定CO₂的高性能可回收多位点催化系统
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-11 DOI: 10.1002/adsc.202500246
Saddam Hossain, Yu Hoshino, Hisashi Shimakoshi
{"title":"High‐Performance and Recyclable Multisite Catalytic System for CO₂ Fixation Using Crown Ether‐Linked Schiff Base and Alkali Halides","authors":"Saddam Hossain, Yu Hoshino, Hisashi Shimakoshi","doi":"10.1002/adsc.202500246","DOIUrl":"https://doi.org/10.1002/adsc.202500246","url":null,"abstract":"The development of efficient and sustainable catalytic systems for CO&lt;sub&gt;2&lt;/sub&gt; fixation is crucial for carbon‐neutral chemical processes. We now report a high‐performance and recyclable multisite catalytic system based on a crown ether‐linked Schiff base in combination with alkali halides for the synthesis of cyclic carbonates from epoxides and CO&lt;sub&gt;2&lt;/sub&gt;. The designed catalyst features multiple active sites, including a Lewis acidic alkali ion center and a nucleophilic iodide source, enabling the efficient activation of epoxides under solvent‐free conditions with atmospheric pressure. Systematic studies on the effects of cations and calcium salts revealed that the multi‐activation mechanism plays a critical role in enhancing the catalytic performance. The catalyst exhibited a high selectivity and activity, achieving up to a 97 % yield of cyclic carbonates at atmospheric CO&lt;sub&gt;2&lt;/sub&gt; pressure and 70 °C. The simulated post‐combustion exhaust gas (CO&lt;sub&gt;2&lt;/sub&gt;: 7.5 %, N&lt;sub&gt;2&lt;/sub&gt;: 92.5 %, relative humidity: 90 %) was concentrated to 97 % and used as the material for the reaction to yield 90 % of styrene carbonate from styrene oxide. Furthermore, the catalyst was easily recovered and reused for multiple cycles without any significant loss of activity. This study provides a practical and environmentally‐friendly approach for CO&lt;sub&gt;2&lt;/sub&gt; utilization, contributing to the advancement of sustainable catalytic processes.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"12 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143818942","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
eAmidation: An Electrochemical Amidation of Aldehydes via the Oxidation of N-Aryl Hydrazones 酰胺化：通过氧化n -芳基腙对醛的电化学酰胺化
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-10 DOI: 10.1002/adsc.202500037
Luke Chen, James Thompson, Craig Jamieson
{"title":"eAmidation: An Electrochemical Amidation of Aldehydes via the Oxidation of N-Aryl Hydrazones","authors":"Luke Chen, James Thompson, Craig Jamieson","doi":"10.1002/adsc.202500037","DOIUrl":"https://doi.org/10.1002/adsc.202500037","url":null,"abstract":"In recent years, the use of electrochemistry has emerged as a powerful yet sustainable means of enabling key transformations. Amidation is one of the most frequently executed transformations in synthetic chemistry, and using an electrochemical approach, the current study has demonstrated the synthesis of amides from aldehydes and amines. Mechanistic work indicates that the reaction proceeds via the oxidation of an intermediate hydrazone to generate an acyl diazene as the acylating species. The protocol developed has enabled the synthesis of a broad range of amides, including access to pharmaceutically relevant products, directly from aldehydes without recourse for hazardous chemical oxidants and activating agents.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"4 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143819960","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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