Advanced Synthesis & Catalysis最新文献

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Construction of meta-Disubstituted Triaryls via Iodine-Catalyzed Oxidative Aromatization Coupling of Cycloalkenes with Indoles 碘催化环烯烃与吲哚氧化芳构偶联构建间二取代三芳基
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-19 DOI: 10.1002/adsc.70130
Yang Yang, Heng Liu, Zhi-Hui Wang, Yilitabaier Julaiti, Yanhua Lu, Boshun Wan, Xiao-Feng Wu, Qing-An Chen
{"title":"\u0000Construction of meta-Disubstituted Triaryls via Iodine-Catalyzed Oxidative Aromatization Coupling of Cycloalkenes with Indoles","authors":"Yang Yang, Heng Liu, Zhi-Hui Wang, Yilitabaier Julaiti, Yanhua Lu, Boshun Wan, Xiao-Feng Wu, Qing-An Chen","doi":"10.1002/adsc.70130","DOIUrl":"https://doi.org/10.1002/adsc.70130","url":null,"abstract":"<i>meta</i>-Disubstituted triaryls are privileged scaffolds in bioactive molecules and functional materials, but their efficient synthesis remains challenging, due to limitations in regioselectivity and reliance on prefunctionalized substrates or transition metals. Herein, an iodine-catalyzed oxidative aromatization strategy is reported for the construction of <i>meta</i>-triaryls via direct coupling of readily available cycloalkenes with indoles. This protocol enables regioselective C<span></span>C bond formation at the indole C3-position and a subsequent dehydrogenative desaturation of the cycloalkene component to form the <i>meta</i>-substituted arene motif. The method features broad substrate scope, accommodating diverse substituted cycloalkenes and indoles. Key advantages include economical catalyst (HI as iodine source), avoidance of precious metals, and operational simplicity. Additionally, the products can undergo an array of synthetic transformations, including heterocycle skeleton editing to quinolines, halogenations, and photoredox functionalizations, which highlight the potential applications of this strategy.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"22 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145089390","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 Advances in Ene Reactions with Carbon Enophiles 烯与亲碳亲烯试剂反应的最新进展
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-18 DOI: 10.1002/adsc.70122
Thomas J. J. Müller
{"title":"Recent Advances in Ene Reactions with Carbon Enophiles","authors":"Thomas J. J. Müller","doi":"10.1002/adsc.70122","DOIUrl":"https://doi.org/10.1002/adsc.70122","url":null,"abstract":"Ene reactions are inter- or intramolecular addition reactions between a four-electron \"ene\" component and a two-electron enophile functionality, in which two <i>π</i>-bonds and a C–H (or metal–C) <i>σ</i>-bond are rearranged into one <i>π</i>-bond and two <i>σ</i>-bonds. One of the newly formed <i>σ</i>-bonds is a carbon–carbon bond, while the other is the rearranged a C–H (or metal–C) bond. This transformation enables the formation of structurally and functionally complex ene products in a single step. Originally, ene reactions were discovered as concerted and stepwise pericyclic elementary processes. However, increasing mechanistic insight—gained through both experimental and computational studies—along with extensive empirical methodological work, has paved the way to a plethora of ene-type reactions involving carbon enophiles. Since 2012, the already well-established transition metal-catalyzed variants of ene reactions have significantly expanded. Moreover, highly reactive aryne intermediates—generated in situ either by fluoride induced elimination from <i>ortho</i>-silyl aryltriflates at room temperature, or by hexadehydro-Diels–Alder reaction of a 1,3-diyne with an alkyne (both inter- and intramolecularly)—find increasing application in novel ene-type sequences. Propargyl ene reactions also gain traction, particularly because the resulting ene-allenes serve as highly valuable intermediates in the design of domino sequences that lead to complex polycyclic fused structures. Finally, the implementation of ene reactions in polymer chemistry for the synthesis of functionalized polymers and renewable unsaturated raw materials has emerged as a promising alternative to the use of purely petrochemistry based substrates.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"22 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145078497","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
A Versatile Route to 3,3-Disubstituded Phthalides Via Arylogous Michael Addition Catalyzed by Organic Base 有机碱催化芳基迈克尔加成制备3,3-二取代邻苯二甲酸酯的通用途径
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-18 DOI: 10.1002/adsc.70128
Enzo Eddebbarh, Lou Mazoyer, Jérôme Thibonnet, Julien Petrignet
{"title":"A Versatile Route to 3,3-Disubstituded Phthalides Via Arylogous Michael Addition Catalyzed by Organic Base","authors":"Enzo Eddebbarh, Lou Mazoyer, Jérôme Thibonnet, Julien Petrignet","doi":"10.1002/adsc.70128","DOIUrl":"https://doi.org/10.1002/adsc.70128","url":null,"abstract":"The 3,3-disubstituted phthalide scaffold, a privileged structure in medicinal chemistry and natural product synthesis, serves as a key motif in many bioactive compounds. Leveraging the solvent-dependent pKa modulation of organic bases, this study introduces a mild, organocatalytic Michael addition protocol for coupling diverse 3-arylphthalides with Michael acceptors. The method demonstrates broad functional group tolerance, accommodating electron-donating and electron-withdrawing substituents. The versatility of this methodology is highlighted by mild reaction conditions, short reaction times, and gram-scale feasibility. Finally, the approach may open the gate to asymmetric catalysis, offering access to enantiomerically enriched phthalides.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"1 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145084133","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
Chemodivergent Higher-Order Annulation of Azaheptafulvenes with Enals Through N-Heterocyclic Carbene Catalysis 氮杂环碳催化氮杂七富尔烯与烯醛的高阶化学发散环化
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-18 DOI: 10.1002/adsc.70127
Yiwen Zhang, Yangjie Yu, Min Xia, Zhen Wang, Manman Sun, Weijun Yao
{"title":"Chemodivergent Higher-Order Annulation of Azaheptafulvenes with Enals Through N-Heterocyclic Carbene Catalysis","authors":"Yiwen Zhang, Yangjie Yu, Min Xia, Zhen Wang, Manman Sun, Weijun Yao","doi":"10.1002/adsc.70127","DOIUrl":"https://doi.org/10.1002/adsc.70127","url":null,"abstract":"A base-directed, chemodivergent, higher-order annulation between azaheptafulvenes and enals has been developed through <i>N</i>-heterocyclic carbene catalysis. In the presence of an <i>N</i>-heterocyclic carbene organocatalyst, DBU promotes an [8 + 3] annulation with excellent chemo- and diastereoselectivities, whereas the reaction proceeds via an [8 + 2] annulation when potassium carbonate is used as the base. In addition, the reaction can be carried out on a gram scale, and the products are efficiently converted into bicyclic derivatives.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"30 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145078496","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
Visible-Light Photocatalyzed Selective Synthesis of 1,2- or 1,3-Dithianes From Thietanes: An Experimental and Theoretical Study 可见光催化从硫烷选择性合成1,2-或1,3-二硫烷的实验和理论研究
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-18 DOI: 10.1002/adsc.70125
Gabriel Cormier, Manuel Pedrón, Maria I. Lapuh, Regis Guillot, Ilaria Ciofini, Thomas Boddaert
{"title":"Visible-Light Photocatalyzed Selective Synthesis of 1,2- or 1,3-Dithianes From Thietanes: An Experimental and Theoretical Study","authors":"Gabriel Cormier, Manuel Pedrón, Maria I. Lapuh, Regis Guillot, Ilaria Ciofini, Thomas Boddaert","doi":"10.1002/adsc.70125","DOIUrl":"https://doi.org/10.1002/adsc.70125","url":null,"abstract":"Unlike other sulfur-containing heterocycles, the potential applications of functionalized dithianes have been less explored to date due to their challenging synthesis. To address this issue, we herein leverage the straightforward access to functionalized thietanes and describe a selective photochemical ring enlargement of the latter to 1,2- or 1,3-dithianes using thiocarbonyl substrates, which are in situ generated via a Norrish-type II fragmentation reaction. The library of dithianes obtained by this photocatalyzed domino sequence between diversely substituted thietanes and various thiocarbonyls revealed regioselectivity rules: excited thioketones lead exclusively to 1,2-dithianes, while excited thioaldehydes selectively yield 1,3-dithianes, where 1,2-dithianes serve as precursors to their regioisomers. The ring expansion reaction leading to 1,2-dithianes was also integrated into a triple photochemical cascade, where the thietane intermediates were obtained via a thia-Paternò<sup>_</sup>Büchi reaction between Norrish-II thiocarbonyl products and various alkene partners. These experimental results were complemented with time-dependent density functional theory calculations, which support the complex chemical pathway, rationalize the observed regioselectivity, and further substantiate mechanistic proposals related to the photolysis of disulfide bridges in peptides.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"155 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145078493","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
Active‐Site Microenvironments Design of Hydrogenation Catalysts for Enhanced Hydrocracking of Heavy Oil 重油加氢裂化催化剂活性位点微环境设计
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-17 DOI: 10.1002/adsc.70121
Peng Xue, Guangxun Sun, Qian Zhang, Yingying Liu, Shiwen Zhang, Zhidong Wang, Lei Wang, Jiaye Li, Hong Yin, Haifeng Gong, Yuan Pan
{"title":"Active‐Site Microenvironments Design of Hydrogenation Catalysts for Enhanced Hydrocracking of Heavy Oil","authors":"Peng Xue, Guangxun Sun, Qian Zhang, Yingying Liu, Shiwen Zhang, Zhidong Wang, Lei Wang, Jiaye Li, Hong Yin, Haifeng Gong, Yuan Pan","doi":"10.1002/adsc.70121","DOIUrl":"https://doi.org/10.1002/adsc.70121","url":null,"abstract":"Slurry phase hydrocracking (SPHC) is one of the effective ways to achieve efficient conversion of low‐quality heavy oil. The active‐site structural design of catalysts is crucial to improve the performance but is still challenging. However, up to now, few reviews on the active‐site microenvironments design of catalyst for enhancing SPHC performance have been reported. Herein, this review summarizes the research progress on the active‐site microenvironments regulation strategies of hydrogenation catalysts at the molecular scale for SPHC systematically. Then, based on the problem of low hydrogenation efficiency due to the easy aggregation and low atomic utilization of molecular catalysts, the design strategies for catalysts on the atomic scale are proposed systematically. Subsequently, the design principles of active‐site microenvironment for hydrogenation catalysts to enhance the SPHC are revealed. Finally, the opportunities and challenges of atomically dispersed catalyst for SPHC are prospected. This review provides an important reference for the design and development of high‐performance hydrogenation catalysts for SPHC of heavy oil.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"16 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145077887","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
Fe‐Photocatalyzed Decarboxylative Giese‐Type Reaction of α‐N, O or S Carboxylic Acids: Insight into the Mechanism of the Radical Formation 铁光催化α - N, O或S羧酸脱羧型反应:自由基形成机制的研究
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-16 DOI: 10.1002/adsc.70114
Fernando Pérez‐Maseda, María Martín, Jorge Labrador‐Santiago, Inés Corral, Diego J. Cárdenas
{"title":"Fe‐Photocatalyzed Decarboxylative Giese‐Type Reaction of α‐N, O or S Carboxylic Acids: Insight into the Mechanism of the Radical Formation","authors":"Fernando Pérez‐Maseda, María Martín, Jorge Labrador‐Santiago, Inés Corral, Diego J. Cárdenas","doi":"10.1002/adsc.70114","DOIUrl":"https://doi.org/10.1002/adsc.70114","url":null,"abstract":"Very simple conditions are described for the Fe‐photocatalyzedaddition of α‐amino, α‐alkoxy, and α‐alkylthio radicals to electron‐deficient alkenes. The reactions proceed under smooth ligandless conditions with inexpensive base and in the absence of oxidant. A mechanistic computational TD‐DFT study on the formation and evolution of the electronic excited states supports for the first time that, after Fe(III)‐carboxylate excitation by visible light, homolytic cleavage of the FeO actually takes place, leading to a carboxyl radical.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"74 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145072099","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 Advances in the Application of Dioxazolones in Transition Metal‐Catalyzed Hydroamidation 二恶唑酮类化合物在过渡金属催化氢酰胺化反应中的应用进展
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-16 DOI: 10.1002/adsc.70124
Xun Tian, Xueyun Cai, Ying Long, Lin Qi, Lindong Luan, Xiaodong Yang
{"title":"Recent Advances in the Application of Dioxazolones in Transition Metal‐Catalyzed Hydroamidation","authors":"Xun Tian, Xueyun Cai, Ying Long, Lin Qi, Lindong Luan, Xiaodong Yang","doi":"10.1002/adsc.70124","DOIUrl":"https://doi.org/10.1002/adsc.70124","url":null,"abstract":"In recent years, research on transition metal‐catalyzed amide synthesis has increasingly emerged as a significant focus. Among the efficient amidation reagents, dioxazolones have demonstrated excellent utility in hydroamidation reactions, enabling the rapid conversion of substrates such as alkenes, alkynes, and enynes into enamine or aliphatic amine derivatives. This review summarizes recent advances in dioxazolone‐enabled hydroamidation, with a detailed discussion of diverse substrate types, including various alkenes, alkynes, and enynes as starting materials. Furthermore, the performance and mechanisms of various transition metal catalysts in these processes have been explored. The synthetic strategies, reaction mechanisms, substrate scope, and practical applications of these transformations are comprehensively analyzed, highlighting the versatility and adaptability of dioxazolones in hydroamidation. We anticipate that this review will provide readers with a clearer understanding of this field, inspire further exploratory research, and advance the development and application of hydroamidations.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"21 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145072432","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
Palladium‐Catalyzed Denitrative Decarboxylation of Nitroarenes with Alkynyl Carboxylic Acids 钯催化硝基芳烃与炔基羧酸的脱羧反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-15 DOI: 10.1002/adsc.70120
Chuan Han, Chau Ming So
{"title":"Palladium‐Catalyzed Denitrative Decarboxylation of Nitroarenes with Alkynyl Carboxylic Acids","authors":"Chuan Han, Chau Ming So","doi":"10.1002/adsc.70120","DOIUrl":"https://doi.org/10.1002/adsc.70120","url":null,"abstract":"A general approach for the decarboxylation of alkynyl carboxylic acids with nitroarenes via denitrative coupling is reported for the first time. The methodology demonstrates broad substrate generality, accommodating diverse nitroaromatics, including electron‐deficient heteroarenes, to deliver aryl alkynes with high efficiency. Notably, this methodology enables the use of nitroarenes and aryl‐substituted carboxylic acids to access diarylacetylene products. Furthermore, this protocol permits efficient synthesis of 3‐substituted benzofuran or isochromen‐1‐one derivatives, which is a challenging regiochemical outcome unattainable through conventional coupling strategies.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"52 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145072368","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 EDA Complex‐Enabled Radical Alkylation/Cyclization Reaction of N‐Arylacrylamides with Katritzky Salts 光诱导EDA配合物激活N -芳烯酰胺与Katritzky盐的自由基烷基化/环化反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-09-13 DOI: 10.1002/adsc.70109
Shun‐Dan Li, Jian‐Hong Fan, Xin‐Ke Yuan, Ao‐Yun Li, Mei‐Jin Gao, Fei Luo, Peng‐Fei Huang, Long‐Jin Zhong, Yu Liu
{"title":"Photoinduced EDA Complex‐Enabled Radical Alkylation/Cyclization Reaction of N‐Arylacrylamides with Katritzky Salts","authors":"Shun‐Dan Li, Jian‐Hong Fan, Xin‐Ke Yuan, Ao‐Yun Li, Mei‐Jin Gao, Fei Luo, Peng‐Fei Huang, Long‐Jin Zhong, Yu Liu","doi":"10.1002/adsc.70109","DOIUrl":"https://doi.org/10.1002/adsc.70109","url":null,"abstract":"As important structural motifs among <jats:italic>N</jats:italic>‐heterocycles, phenanthridines are ubiquitous in significant functional compounds. Herein, a visible‐light‐mediated radical alkylation/cyclization reaction between <jats:italic>N</jats:italic>‐Arylacrylamides and Katritzky salts for the efficient construction of phenanthridines under mild conditions is reported. Triggered by photoexcitation of electron donor–acceptor complexes formed between salts and <jats:italic>N, N</jats:italic>‐diisopropylethylamine, this strategy circumvents the requirement for photocatalysts and transition‐metal catalysts. A series of phenanthridine derivatives are smoothly synthesized in up to 86% yield, demonstrating excellent functional group compatibility.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"37 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145072100","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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