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High-Order Cascade Transformations on Tertiary β-Enaminones for Step-Economical Construction of Molecular Diversity and Complexity 叔β-胺酮的高阶级联变换用于分子多样性和复杂性的阶梯经济构建
IF 4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-06-09 DOI: 10.1002/adsc.9583
Chenxu Wang, Jianchao Liu, Jie-Ping Wan
{"title":"High-Order Cascade Transformations on Tertiary β-Enaminones for Step-Economical Construction of Molecular Diversity and Complexity","authors":"Chenxu Wang,&nbsp;Jianchao Liu,&nbsp;Jie-Ping Wan","doi":"10.1002/adsc.9583","DOIUrl":"10.1002/adsc.9583","url":null,"abstract":"<p>The generation of molecular diversity and complexity constitutes the major task of synthetic organic chemistry. In contrast, to achieve the maximum complexity and/or diversity of organic compound with minimum operational steps is of high significance by saving consumption of both the chemicals and the time for synthesis, enhancing the synthetic efficiency and sustainability. Based on our longstanding interest in the enaminone-based organic synthesis, herein, the research advances in high-order cascade reactions are reviewed, which involve in the formation of at least four new chemical bonds, including <i>sigma</i>-, <i>pi</i>-bonds and C<span></span>H bond, in one reaction of enaminones, showing how the high-step economy is achieved in the enaminone-based synthetic reactions. Since the known results all involves in the cyclization, the contents of the current manuscript are divided into two main sections: the single cyclization reaction and bicyclic annulation reaction.</p>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 14","pages":""},"PeriodicalIF":4.0,"publicationDate":"2025-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144252845","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
Total Synthesis of (−)-2-Oxokolavenol: A Natural Neoclerodane Diterpene with Farnesoid X Receptor Transcriptional Activity （−）‐2‐Oxokolavenol的全合成：一种具有Farnesoid X受体转录活性的天然新氯烷二萜
IF 4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-06-09 DOI: 10.1002/adsc.9582
Da-Yu Shi, Wen-Bo Ye, Rui Ding, Ding-Ding Gao, Yi-Wen Zhao, Cheng Huang, Ping Tian
{"title":"Total Synthesis of (−)-2-Oxokolavenol: A Natural Neoclerodane Diterpene with Farnesoid X Receptor Transcriptional Activity","authors":"Da-Yu Shi,&nbsp;Wen-Bo Ye,&nbsp;Rui Ding,&nbsp;Ding-Ding Gao,&nbsp;Yi-Wen Zhao,&nbsp;Cheng Huang,&nbsp;Ping Tian","doi":"10.1002/adsc.9582","DOIUrl":"10.1002/adsc.9582","url":null,"abstract":"<p>The natural neoclerodane diterpene (−)-2-oxokolavenol is isolated from the twigs of <i>Amoora stellato-squamosa</i>, and exhibited significant Farnesoid X receptor (FXR) transcriptional activity with an EC<sub>50</sub> value of 1.877 μM. However, the scarcity of its natural sources poses a considerable challenge for further biological studies. To address this limitation, herein, the first total synthesis of (−)-2-oxokolavenol is reported. This synthesis features stereoselective alkylation, regioselective redox transformations (including late-stage allylic oxidation), and strategic installation of methyl groups. The overall synthesis delivers (−)-2-oxokolavenol in 15 steps from the cheap and readily available Wieland–Miescher ketone. In addition, this approach allows (−)-2-oxokolavenol with 12 synthetic intermediates for biological evaluations by using dual-luciferase reporter assay. Preliminary investigations confirm the nuclear receptor selectivity of (−)-2-oxokolavenol as a FXR agonist, underscoring its potential for further bioactivity studies.</p>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 14","pages":""},"PeriodicalIF":4.0,"publicationDate":"2025-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144252245","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
C–H Homocoupling of Arenes via Pd/S,O-Ligand Catalysis Pd/S， o -配体催化芳烃C-H均偶联
IF 4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-06-09 DOI: 10.1002/adsc.9588
Ke-Zuan Deng, Sam Pikavet, Paola Riente, María Ángeles Fernández-Ibáñez
{"title":"C–H Homocoupling of Arenes via Pd/S,O-Ligand Catalysis","authors":"Ke-Zuan Deng,&nbsp;Sam Pikavet,&nbsp;Paola Riente,&nbsp;María Ángeles Fernández-Ibáñez","doi":"10.1002/adsc.9588","DOIUrl":"10.1002/adsc.9588","url":null,"abstract":"<p>Non-directed Pd-catalyzed oxidative dehydrogenative homocoupling of arenes is achieved in the presence of an S,O-ligand. The reaction proceeds under aerobic and mild reaction conditions with a wide range of anisole derivatives, providing direct access to symmetric biaryls with excellent <i>ortho</i>-<i>ortho</i> or <i>para</i>-<i>para</i> regioselectivity. Notably, the use of the arene as the limiting reagent enables late-stage functionalization of complex pharmaceutical molecules. The industrial applicability of this methodology is demonstrated through the synthesis of the Upilexmonomer via the homocoupling of unactivated<i>o</i>-xylene.</p>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 14","pages":""},"PeriodicalIF":4.0,"publicationDate":"2025-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.9588","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144260164","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
Pd-Catalyzed Regio- and Stereoselective Ring-Opening Hydrosulfonylation of Methylenecyclopropanes for Branched Allylic Sulfones 钯催化甲基环丙烷对支化烯丙基砜的区域和立体选择性开环氢磺化反应
IF 4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-06-08 DOI: 10.1002/adsc.9589
Bu-Hong Zhang, Jia-Xin Song, Bai-Lin Wang, Zhi-Xiong Ou, Li-Bo Li, Xing-Wang Wang
{"title":"Pd-Catalyzed Regio- and Stereoselective Ring-Opening Hydrosulfonylation of Methylenecyclopropanes for Branched Allylic Sulfones","authors":"Bu-Hong Zhang,&nbsp;Jia-Xin Song,&nbsp;Bai-Lin Wang,&nbsp;Zhi-Xiong Ou,&nbsp;Li-Bo Li,&nbsp;Xing-Wang Wang","doi":"10.1002/adsc.9589","DOIUrl":"10.1002/adsc.9589","url":null,"abstract":"<p>A Pd-catalyzed ring-opening hydrosulfonylation reaction of methylenecyclopropanes with sulfonyl hydrazides was developed, which produced a series of branched (<i>E</i>)-allylic sulfones in 52−91% yields. In addition, the asymmetric variant was also investigated, and the optically active products were obtained in moderate yields with good enantioselectivities (up to 94:6 er). Mechanistic studies suggested that the reaction proceeds through the formation of an allyl hydrazine intermediate and subsequent rearrangement to the branched (<i>E</i>)-allylic sulfone products. Generally, the reaction was completed in one pot under mild reaction conditions, which also featured in good functional group tolerance, broad substrate scope, high regiospecificity, branched selectivity, as well as atom and step economy.</p>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 14","pages":""},"PeriodicalIF":4.0,"publicationDate":"2025-06-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144237764","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
Synergistic Radical Markovnikov Hydroselenization of Alkenes 烯烃的协同自由基Markovnikov加氢硒化反应
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-06-03 DOI: 10.1002/adsc.202500120
Gefei Duan , Yunbo Zhu
{"title":"Synergistic Radical Markovnikov Hydroselenization of Alkenes","authors":"Gefei Duan ,&nbsp;Yunbo Zhu","doi":"10.1002/adsc.202500120","DOIUrl":"10.1002/adsc.202500120","url":null,"abstract":"<div><div>Herein, we report a new synergistic radical Markovnikov hydroselenization of alkenes by in‐situ generated selenium cluster that absorbs hydride under mild conditions. In this protocol, a formal “metal hydride” mechanism is proposed, in which the hydrogen atom is added into the alkene, then undergoing S<sub>H</sub>2 radical substitution to give the dialkyl selenides products that previously are inaccessible. This metal‐free double selenium‐ene reaction enables smoothly the installation of the bioactive Se atom into a remarkably wide scope of aliphatic and aromatic alkenes and pharmaceuticals‐derived alkenes along with high functional groups compatibility.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 11","pages":"Article e202500120"},"PeriodicalIF":4.4,"publicationDate":"2025-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745092","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
Understanding Chiral Proton Catalysis Using Cinchonium Derivatives in aza‐Michael Additions 在aza - Michael加成物中使用金chonium衍生物了解手性质子催化
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-06-03 DOI: 10.1002/adsc.202401458
Fernando Auria‐Luna , Eugenia Marqués‐López , M. Concepción Gimeno , Juan V. Alegre‐Requena , Raquel P. Herrera
{"title":"Understanding Chiral Proton Catalysis Using Cinchonium Derivatives in aza‐Michael Additions","authors":"Fernando Auria‐Luna ,&nbsp;Eugenia Marqués‐López ,&nbsp;M. Concepción Gimeno ,&nbsp;Juan V. Alegre‐Requena ,&nbsp;Raquel P. Herrera","doi":"10.1002/adsc.202401458","DOIUrl":"10.1002/adsc.202401458","url":null,"abstract":"<div><div>This work presents a detailed mechanistic study of a quininium‐catalyzed aza‐Michael reaction, providing essential information for advancing chiral proton catalysis (CPC). The use of cinchona derivatives as chiral proton catalysts demonstrates their potential beyond their conventional roles as base‐promoted and phase‐transfer catalysts. Competitive reaction pathways are explored using density functional theory (DFT), wavefunction theory, and microkinetic simulations. Theoretical analyses are complemented with experimental titration and kinetic techniques to verify the intrinsic details of the reaction. This study reveals an intricate hydrogen bond network formed in the rate‐ and selectivity‐determining step, involving four noncovalently attached components that favor a stronger substrate⋅⋅⋅catalyst interaction in the <em>R</em> transition state. Significantly, this research emphasizes the pivotal role of carboxylate anions as nucleophile‐activating bases impacting reaction yield and enantioselectivity. Therefore, this work introduces cinchonium derivatives as new options for CPC and provides a thorough mechanistic analysis significant in expanding this underdeveloped catalytic domain.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 11","pages":"Article e202401458"},"PeriodicalIF":4.4,"publicationDate":"2025-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143713285","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 Furans/Pyrroles through Palladium‐Gold Relay Catalyzed Skeletal Editing of Carbonates or Carbamates via a Decarboxylative‐Aromatization Strategy 钯金接力催化羰基或氨基甲酸酯骨架编辑合成呋喃/吡咯
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-06-03 DOI: 10.1002/adsc.202500198
Xiyuan Zhang , Bo Jang , Yang Yang , Rui Dong , Jiapeng Ding , Zhiwei Miao
{"title":"Synthesis of Furans/Pyrroles through Palladium‐Gold Relay Catalyzed Skeletal Editing of Carbonates or Carbamates via a Decarboxylative‐Aromatization Strategy","authors":"Xiyuan Zhang ,&nbsp;Bo Jang ,&nbsp;Yang Yang ,&nbsp;Rui Dong ,&nbsp;Jiapeng Ding ,&nbsp;Zhiwei Miao","doi":"10.1002/adsc.202500198","DOIUrl":"10.1002/adsc.202500198","url":null,"abstract":"<div><div>A novel Pd(0)/Au(I) relay catalysis strategy for converting propargylic cyclic carbonates into furans is reported. The method capitalizes on the sequential transformation of a palladium‐stabilized alkoxide‐π‐allyl intermediate into a gold‐stabilized dihydrofuran species, enabled by the cooperative action of palladium and gold catalysts. This approach is notable for its simplicity, broad functional group compatibility, and use of readily available substrates. By extending the methodology to five‐membered carbamates substrates, the construction of pyrrole frameworks is also demonstrated. Additionally, the method facilitates the synthesis of polycyclic furans and pyrroles via Diels‐Alder reactions, achieving high yields with excellent diastereoselectivities.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 11","pages":"Article e202500198"},"PeriodicalIF":4.4,"publicationDate":"2025-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143724001","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‐Mediated Synthesis of 3‐Chlorobenzo[b]thiophenes Using Polychloromethanes as Solvent and Halogen Source 以聚氯甲烷为溶剂和卤素源，可见光介导合成3-氯苯并[b]噻吩
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-06-03 DOI: 10.1002/adsc.202500253
Mei‐Ling Yang , Jing‐Yi Cao , Ying‐Jian Wu , Xiaohu Yang , Wen‐Chao Yang , Jian‐Jun Wang
{"title":"Visible‐Light‐Mediated Synthesis of 3‐Chlorobenzo[b]thiophenes Using Polychloromethanes as Solvent and Halogen Source","authors":"Mei‐Ling Yang ,&nbsp;Jing‐Yi Cao ,&nbsp;Ying‐Jian Wu ,&nbsp;Xiaohu Yang ,&nbsp;Wen‐Chao Yang ,&nbsp;Jian‐Jun Wang","doi":"10.1002/adsc.202500253","DOIUrl":"10.1002/adsc.202500253","url":null,"abstract":"<div><div>This study developed a novel strategy based on visible‐light photocatalysis for the construction of 3‐chlorobenzo[<em>b</em>]thiophenes. The photocatalytic system exhibits multiple advantages, including mild reaction conditions, cascade reaction, and good tolerance. Mechanistic studies have demonstrated that the chlorine radicals, generated from polychloromethanes, are the key to initiating the tandem reaction.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 11","pages":"Article e202500253"},"PeriodicalIF":4.4,"publicationDate":"2025-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143798449","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‐Heterocyclic Carbene‐Diboron‐Substrate Cooperatively Facilitate Direct Amidation of Carboxylic Acids and Amines n-杂环碳-二硼-底物协同促进羧酸和胺的直接酰胺化
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-06-03 DOI: 10.1002/adsc.202401441
Di Wu , Yang Wang , Sheng Tao , Tao Wang , Fei Chen , Zhi‐Hong Du , Chun‐Bo Bo , Min Li , Bin Dai , Donghui Wei , Ning Liu
{"title":"N‐Heterocyclic Carbene‐Diboron‐Substrate Cooperatively Facilitate Direct Amidation of Carboxylic Acids and Amines","authors":"Di Wu ,&nbsp;Yang Wang ,&nbsp;Sheng Tao ,&nbsp;Tao Wang ,&nbsp;Fei Chen ,&nbsp;Zhi‐Hong Du ,&nbsp;Chun‐Bo Bo ,&nbsp;Min Li ,&nbsp;Bin Dai ,&nbsp;Donghui Wei ,&nbsp;Ning Liu","doi":"10.1002/adsc.202401441","DOIUrl":"10.1002/adsc.202401441","url":null,"abstract":"<div><div>Herein, we report that an efficient and practical organocatalyzed strategy enables direct amidation of a wide range of carboxylic acids and variety of amines. The organocatalyzed system is proved to be suitable for the synthesis of small molecular peptides from protected amino acids, and the method was successfully applied to the late stage functionalization of drug molecules or pharmaceutical intermediates. Mechanistic studies by control experiments, in situ infrared spectroscopy, <sup>11</sup>B nuclear magnetic resonance (<sup>11</sup>B NMR), and density functional theory (DFT) calculation, reveal that <em>N</em>‐propyl‐<em>N</em>‐(2‐(pyridin‐2‐ylamino)phenyl) formamide reacts with B<sub>2</sub>pin<sub>2</sub> to form the <em>N</em>‐heterocyclic carbene (NHC)‐diboron adduct, and the boron atom of NHC‐diboron adduct is able to coordinate to the carboxyl oxygen atom of the carboxylic acid to generate the true active species of NHC‐diboron‐carboxylic acid for catalyzing the amidation of carboxylic acids and amines. The discovery of in situ generation of catalytic system in combination of multi‐catalytic components with substrates may open the door to cooperative catalysis for the synthesis of important organic molecules.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 11","pages":"Article e202401441"},"PeriodicalIF":4.4,"publicationDate":"2025-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143661089","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
Nickel‐Catalyzed Transannulation Reaction of 1,2,3,4‐Benzothiatriazin‐1,1(2H)‐dioxide with Alkyne and the Detailed Investigation of Reaction Mechanism 镍催化1,2,3,4-苯并噻唑嗪-1,1(2H)-二氧化物与炔的转环反应及反应机理的详细研究
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-06-03 DOI: 10.1002/adsc.202500231
Vijaykumar H. Thorat , Ya‐Chu Chuang , Chung‐Hung Hsieh , Jen‐Chieh Hsieh
{"title":"Nickel‐Catalyzed Transannulation Reaction of 1,2,3,4‐Benzothiatriazin‐1,1(2H)‐dioxide with Alkyne and the Detailed Investigation of Reaction Mechanism","authors":"Vijaykumar H. Thorat ,&nbsp;Ya‐Chu Chuang ,&nbsp;Chung‐Hung Hsieh ,&nbsp;Jen‐Chieh Hsieh","doi":"10.1002/adsc.202500231","DOIUrl":"10.1002/adsc.202500231","url":null,"abstract":"<div><div>Herein, we provide two nickel complexes and a series of control experiments to study the mechanism of the nickel‐catalyzed transannulation reaction of 1,2,3,4‐benzo‐thiatriazin‐1,1(2<em>H</em>)‐dioxide with aryne and alkyne in detail. In addition, we provide a new protocol for the cycloaddition of 1,2,3,4‐benzothiatriazin‐1,1(2<em>H</em>)‐dioxide with alkyne on the basis of a similar reaction pathway.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 11","pages":"Article e202500231"},"PeriodicalIF":4.4,"publicationDate":"2025-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143627707","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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