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Organophotoredox‐Catalyzed Functionalization of Spiro‐Dihydroquinazolinones with Morita–Baylis–Hilman Adducts Morita-Baylis-Hilman加合物催化的螺-二氢喹唑啉酮有机光氧化还原功能化
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-07-30 DOI: 10.1002/adsc.70043
Saikat Mondal, Bathula Maheswari, Abuthayir Mohamathu Ghouse, Srirama Murthy Akondi
{"title":"Organophotoredox‐Catalyzed Functionalization of Spiro‐Dihydroquinazolinones with Morita–Baylis–Hilman Adducts","authors":"Saikat Mondal, Bathula Maheswari, Abuthayir Mohamathu Ghouse, Srirama Murthy Akondi","doi":"10.1002/adsc.70043","DOIUrl":"https://doi.org/10.1002/adsc.70043","url":null,"abstract":"An organophotoredox‐catalyzed, chemo‐ and regio‐selective C–C bond formation between spiro‐dihydroquinazolinones and Morita–Baylis–Hilman adducts has been reported. This transformation proceeds via an aromatization driven deconstructive formation of an alkyl radical and its subsequent selective addition at SN<jats:sub>2</jats:sub>′ position of MBH acetates, resulting in alkene‐ containing quinazolinones. Mild reaction conditions, good substrate‐scope and further modification of resultant products are the noteworthy accomplishments of this methodology.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"20 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144747366","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
Front Cover Picture: Regio-, Stereoselective, Aerobic and Metal-Free Synthesis of Z-Vinyl Sulfides: One-Pot Hydroiodination of Internal Alkynes and in situ Sulfenylations (Adv. Synth. Catal. 13/2025) 封面图：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（ad . Synth）。Catal。13/2025)
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-07-24 DOI: 10.1002/adsc.70032
Gloria Morís-Menéndez, Sergio E. García-Garrido, Pablo García-Álvarez, Alejandro Presa Soto, Nicolás Ríos-Lombardía, Joaquín García-Álvarez
{"title":"Front Cover Picture: Regio-, Stereoselective, Aerobic and Metal-Free Synthesis of Z-Vinyl Sulfides: One-Pot Hydroiodination of Internal Alkynes and in situ Sulfenylations (Adv. Synth. Catal. 13/2025)","authors":"Gloria Morís-Menéndez,&nbsp;Sergio E. García-Garrido,&nbsp;Pablo García-Álvarez,&nbsp;Alejandro Presa Soto,&nbsp;Nicolás Ríos-Lombardía,&nbsp;Joaquín García-Álvarez","doi":"10.1002/adsc.70032","DOIUrl":"https://doi.org/10.1002/adsc.70032","url":null,"abstract":"<p><b>Vinyl Sulfides</b></p><p>The two intersecting planes in the artwork represent the tandem sequence of hydroiodination and sulfenylation of internal alkynes, merged in a one-pot protocol. This metal-free transformation, conducted in a deep eutectic solvent (ChI/p-TsOH), enables the efficient and stereoselective synthesis of Z-vinyl sulfides under mild, aerobic conditions without using toxic HI or VOCs. More information can be found in article number 2500388 by Alejandro Presa Soto, Nicolás Ríos-Lombardía, Joaquín García-Álvarez, and co-workers.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 \u0000 </p>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 13","pages":""},"PeriodicalIF":4.4,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.70032","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144688181","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
Asymmetric Strategies for the Synthesis of Enantiopure α‐/β‐/γ‐Thio‐Carboxylic Acids Bearing a Stereocentre at CS Bond C - S键上具有立体中心的对映纯α‐/β‐/γ‐硫代羧酸的不对称合成策略
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-07-23 DOI: 10.1002/adsc.70042
Jingyue Wu, Daniele Castagnolo
{"title":"Asymmetric Strategies for the Synthesis of Enantiopure α‐/β‐/γ‐Thio‐Carboxylic Acids Bearing a Stereocentre at CS Bond","authors":"Jingyue Wu, Daniele Castagnolo","doi":"10.1002/adsc.70042","DOIUrl":"https://doi.org/10.1002/adsc.70042","url":null,"abstract":"Enantiomerically pure <jats:italic>α</jats:italic>‐/<jats:italic>β</jats:italic>‐/<jats:italic>γ</jats:italic>‐thiocarboxylic acids bearing a stereocentre at the C–S bond represent a class of compounds of notable significance in organic and medicinal chemistry. The chirality at the C–S bond presents both challenges and opportunities in synthetic chemistry. Traditionally, the enantioselective synthesis of these <jats:italic>α</jats:italic>‐/<jats:italic>β</jats:italic>‐/<jats:italic>γ</jats:italic>‐thiocarboxylic acids has relied on chiral pool strategies using naturally derived precursors such as amino acids and hydroxycarboxylic acids. In recent years, the expansion of organo‐ and metal‐catalysed methodologies, employing catalysts such as cinchona alkaloids, copper, and rhodium complexes, has led to strategies with improved efficiency and stereocontrol. Additionally, advances in biocatalysis have enabled more sustainable routes toward s these valuable compounds, using enzymes such as hydrolases and nitrilases. Given the growing academic and industrial interest in these compounds, this review provides an overview of the methods developed and the progresses made over the past two decades in the asymmetric synthesis of thiocarboxylic acids bearing a stereocentre at C–S bond.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"18 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144685030","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
Photoresponsive Aerobic Cross‐Dehydrogenative Coupling Reaction with Ammonium Iodide Catalyst 碘化铵催化光响应性好氧交叉脱氢偶联反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-07-14 DOI: 10.1002/adsc.70033
Hikari Kurihara, Hiroko Wasaki, Katsuhiko Moriyama
{"title":"Photoresponsive Aerobic Cross‐Dehydrogenative Coupling Reaction with Ammonium Iodide Catalyst","authors":"Hikari Kurihara, Hiroko Wasaki, Katsuhiko Moriyama","doi":"10.1002/adsc.70033","DOIUrl":"https://doi.org/10.1002/adsc.70033","url":null,"abstract":"A photoresponsive aerobic cross‐dehydrogenative coupling reaction of <jats:italic>N</jats:italic>‐substituted tetrahydroisoquinolines with nitroalkanes using an iodide salt catalyst under blue LED irradiation is developed, furnishing the CC bond coupling products in high yields. Mechanistic studies indicate that the iodide salt catalyst promotes the single‐electron transfer from the <jats:italic>N</jats:italic>‐substituted tetrahydroisoquinolines to the nitroalkanes through the assembled tetrahydroisoquinoline–iodide salt complex to generate cation radicals of the tetrahydroisoquinolines under light irradiation.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"14 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144622312","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
Catalyst‐Directed Selectivity in Vinylcarbene Reactions: A Comparative Study of Ag, Rh, and Cu Complexes 乙烯基乙烯反应的催化剂定向选择性：Ag、Rh和Cu配合物的比较研究
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-07-13 DOI: 10.1002/adsc.70007
Roger Monreal‐Corona, Àlex Díaz‐Jiménez, Pedro J. Pérez, Ana Caballero, Anna Roglans, Albert Poater, Anna Pla‐Quintana
{"title":"Catalyst‐Directed Selectivity in Vinylcarbene Reactions: A Comparative Study of Ag, Rh, and Cu Complexes","authors":"Roger Monreal‐Corona, Àlex Díaz‐Jiménez, Pedro J. Pérez, Ana Caballero, Anna Roglans, Albert Poater, Anna Pla‐Quintana","doi":"10.1002/adsc.70007","DOIUrl":"https://doi.org/10.1002/adsc.70007","url":null,"abstract":"A comprehensive mechanistic investigation is conducted to uncover the factors governing the selectivity of Ag, Rh, and Cu catalysts in vinylcarbene‐mediated reactions. The study examines the preference for carbenic versus vinylogous C(sp<jats:sup>3</jats:sup>)H bond insertion, highlighting the critical roles of the electronic and steric properties of transition metal catalysts. Contrary to previous assumptions that the enhanced electrophilic character of the vinylogous position in metal vinyl carbenes is the primary determinant, the findings demonstrate that the stereoelectronic effects of the ligand play a more dominant role. These insights inform the design of catalytic systems with tailored selectivity, advancing predictive catalysis and CH bond functionalization.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"109 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144612853","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
Deazaflavin‐Catalyzed Arylation of White Phosphorus with Aryl Bromides and Chlorides 去氮黄素催化白磷与芳基溴化物和氯化物的芳基化反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-07-13 DOI: 10.1002/adsc.70005
Jannes Rückel, Tetiana Pavlovska, Martin Gawron, Radek Cibulka, Robert Wolf
{"title":"Deazaflavin‐Catalyzed Arylation of White Phosphorus with Aryl Bromides and Chlorides","authors":"Jannes Rückel, Tetiana Pavlovska, Martin Gawron, Radek Cibulka, Robert Wolf","doi":"10.1002/adsc.70005","DOIUrl":"https://doi.org/10.1002/adsc.70005","url":null,"abstract":"A substantial improvement in the challenging photocatalytic arylation of white phosphorus (P<jats:sub>4</jats:sub>) with aryl chlorides and bromides is reported. Using the readily accessible deazaflavin‐based photocatalyst <jats:italic>o</jats:italic>‐Me‐dFl, valuable triarylphosphines (PAr<jats:sub>3</jats:sub>) and tetraarylphosphonium salts ([PAr<jats:sub>4</jats:sub>]X, X = Br, Cl) are synthesized from P<jats:sub>4</jats:sub> under near UV‐LED (365 nm) irradiation in up to 87% combined yield with drastically reduced reaction times compared to previous protocols. <jats:sup>31</jats:sup>P nuclear magnetic resonance spectroscopic monitoring studies and density functional theory calculations provide insights into the reaction pathway. The results represent an important step toward more atom‐efficient and economical photocatalytic P<jats:sub>4</jats:sub> functionalization reactions.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"23 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144612857","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 Synthesis of Indenones from Cyclopropenone via N‐atom Nucleophilicity on Imidazole or Amide 咪唑或酰胺的N原子亲核性催化环丙烯合成茚酮
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-07-13 DOI: 10.1002/adsc.70010
Dong‐Wei Wang, Shuo‐Xun Zheng, Jian‐Quan Liu, Xiang‐Shan Wang
{"title":"Base‐Promoted Synthesis of Indenones from Cyclopropenone via N‐atom Nucleophilicity on Imidazole or Amide","authors":"Dong‐Wei Wang, Shuo‐Xun Zheng, Jian‐Quan Liu, Xiang‐Shan Wang","doi":"10.1002/adsc.70010","DOIUrl":"https://doi.org/10.1002/adsc.70010","url":null,"abstract":"A base‐promoted domino reaction strategy has been developed for the synthesis of 3‐substituted 2‐phenylindenones through the nucleophilic ring‐opening of 2,3‐diphenylcyclopropenone by nitrogen atoms. This protocol encompasses a series of reactions, including Michael addition, ring‐opening, intramolecular Friedel–Crafts cyclization, and dehydrogenation, offering a transition‐metal‐free pathway to efficiently access indenone scaffolds.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"13 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144612854","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
Photocatalytic Polyene Cyclization to Cyclopentyl Thioethers with Consecutive Quaternary Centers in Fluorinated Alcohols 氟化醇中连续季中心环戊基硫醚的光催化多烯环化反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-07-10 DOI: 10.1002/adsc.70030
Nicolás Rascón, Aniruddha Biswas, Tanja Gulder
{"title":"Photocatalytic Polyene Cyclization to Cyclopentyl Thioethers with Consecutive Quaternary Centers in Fluorinated Alcohols","authors":"Nicolás Rascón, Aniruddha Biswas, Tanja Gulder","doi":"10.1002/adsc.70030","DOIUrl":"https://doi.org/10.1002/adsc.70030","url":null,"abstract":"The synthesis of carbocycles bearing consecutive all‐carbon quaternary centers remains a formidable challenge in organic chemistry due to their steric congestion and synthetic inaccessibility. Herein, an efficient and sustainable photocatalytic strategy for the cyclization of polyenes to cyclopentane thioethers using 2,4,6‐triphenylpyrylium tetrafluoroborate (TPT<jats:sup>+</jats:sup>) as a photocatalyst in 1,1,1,3,3,3‐hexafluoroisopropanol (HFIP) is reported. The transformation proceeds via a thiyl radical‐initiated mechanism, forming multiple bonds and quaternary centers in a single step under mild conditions. The method tolerates a broad range of aliphatic and functionalized thiols and exhibits high yields and good diastereoselectivities, the latter strongly depending on the addressed mechanism of the transformation. Mechanistic investigations support a radical pathway initiated by thiol oxidation. This work highlights the potential of combining photocatalysis with microstructured solvent systems to facilitate polyene cyclizations. Overall, it provides a versatile platform for synthesizing sterically congested, biologically relevant carbocyclic frameworks.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"4 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144594015","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
Asymmetric Hydrogenation of Tetrahydro‐γ‐Carboline Derivatives with Phosphine‐Free Ruthenium Diamine Catalysts 用无膦钌二胺催化剂催化四氢γ卡泊啉衍生物的不对称加氢反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-07-10 DOI: 10.1002/adsc.70029
Zi‐Qi Yi, Fei Chen, Yan‐Mei He, Qing‐Hua Fan
{"title":"Asymmetric Hydrogenation of Tetrahydro‐γ‐Carboline Derivatives with Phosphine‐Free Ruthenium Diamine Catalysts","authors":"Zi‐Qi Yi, Fei Chen, Yan‐Mei He, Qing‐Hua Fan","doi":"10.1002/adsc.70029","DOIUrl":"https://doi.org/10.1002/adsc.70029","url":null,"abstract":"A highly efficient asymmetric hydrogenation of tetrahydro‐<jats:italic>γ</jats:italic>‐carboline derivatives catalyzed by phosphine‐free ruthenium diamine catalysts has been developed, providing the corresponding <jats:italic>cis</jats:italic>‐hexahydro‐<jats:italic>γ</jats:italic>‐carbolines with excellent enantioselectivities and diastereoselectivities (up to 99% ee and &gt;20:1 dr). Furthermore, this catalytic protocol is applicable to the gram‐scale synthesis of cardioprotective drug (‐)‐stobadin.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"4 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144593943","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 Cascade Cyclization for Selenobenzothiophenes: Synthesis, Photochemistry, and Bioactivity 硒苯并噻吩的电化学级联环化：合成、光化学和生物活性
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-07-10 DOI: 10.1002/adsc.70014
Balati Hasimujiang, Wenyan Xu, Yongjie Yang, Jinghua Huang, Qingbin Yuan, Xinwei Hu, Mu Chen, Zhixiong Ruan
{"title":"Electrochemical Cascade Cyclization for Selenobenzothiophenes: Synthesis, Photochemistry, and Bioactivity","authors":"Balati Hasimujiang, Wenyan Xu, Yongjie Yang, Jinghua Huang, Qingbin Yuan, Xinwei Hu, Mu Chen, Zhixiong Ruan","doi":"10.1002/adsc.70014","DOIUrl":"https://doi.org/10.1002/adsc.70014","url":null,"abstract":"A mild and highly efficient metal‐ and oxidant‐free electrochemical approach for the synthesis of 3‐selenylated benzothiophene derivatives is described. In this innovative electrochemical cascade cyclization reaction, the selenylated benzothiophene skeletons can be constructed along with the formation of CSe and CS bonds in a single step. Moreover, this electrochemical protocol exhibits good functional group compatibility, paving the way for the construction of diverse selenylated benzothiophene compounds with various functional groups from readily available starting materials under an aerobic reaction condition. Meanwhile, a series of control experiments are carried out, and a reasonable reaction mechanism is proposed. Finally, the scaled‐up reactions are performed, and then the photochemical and bioactive properties of the synthesized compounds are elaborately discussed.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"10 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144594016","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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