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Advanced Synthesis & Catalysis最新文献

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Synergistic Radical Markovnikov Hydroselenization of Alkenes
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-01 DOI: 10.1002/adsc.202500120
Gefei Duan, Yunbo Zhu
{"title":"Synergistic Radical Markovnikov Hydroselenization of Alkenes","authors":"Gefei Duan, Yunbo Zhu","doi":"10.1002/adsc.202500120","DOIUrl":"https://doi.org/10.1002/adsc.202500120","url":null,"abstract":"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 SH2 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.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"6 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-01","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
One‐pot Synthesis of 2H‐imidazoles from 1,2‐Diketones, Ketones, and Ammonium Acetate
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-01 DOI: 10.1002/adsc.202500094
Bin Tan, Hanming Yang, Feng Zhao
{"title":"One‐pot Synthesis of 2H‐imidazoles from 1,2‐Diketones, Ketones, and Ammonium Acetate","authors":"Bin Tan, Hanming Yang, Feng Zhao","doi":"10.1002/adsc.202500094","DOIUrl":"https://doi.org/10.1002/adsc.202500094","url":null,"abstract":"Herein, we report a multicomponent reaction for the efficient synthesis of polysubstituted 2H‐imidazoles from readily available 1,2‐diketones, ketones, and ammonium acetate under transition‐metal‐free conditions. Both nitrogen atoms in the resulting 2H‐imidazole products are derived from the cost‐effective inorganic ammonium acetate. This protocol achieves the cleavage of three C–O bonds and the formation of four C–N bonds in a single operation. The advantages of this protocol include low cost, broad substrate scope, good functional group tolerance, and high atom‐ and step‐economy.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"1 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745094","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
Ligand controlled regio‐divergent [2+2+2] cyclotrimerization of alkynes by merging electrochemistry and nickel catalysis
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-01 DOI: 10.1002/adsc.202500121
Yueyue Ma, Caixia Liu, Dali Yang, Yi Shen, Xin Wang, Ziqi Fang, Wenhui Huang, Ruihua Cheng, Jinxing Ye
{"title":"Ligand controlled regio‐divergent [2+2+2] cyclotrimerization of alkynes by merging electrochemistry and nickel catalysis","authors":"Yueyue Ma, Caixia Liu, Dali Yang, Yi Shen, Xin Wang, Ziqi Fang, Wenhui Huang, Ruihua Cheng, Jinxing Ye","doi":"10.1002/adsc.202500121","DOIUrl":"https://doi.org/10.1002/adsc.202500121","url":null,"abstract":"Transition metal catalyzed [2+2+2] cycloaddition reactions between three alkynes, a diyne and an alkyne, or a triyne offer a straightforward and typical protocol toward all kinds of polysubstituted benzens. Herein, the synthesis of polysubstituted aromatics through electrochemical nickel catalyzed cyclotrimerization of alkynes is developed. The regio‐divergent cyclotrimerization of terminal alkynes was achieved by judicious choice of ligands. And tributylphosphine, sterically hindered bipyridine or β‐diketone ligands delivered 1,2,4‐ and 1,3,5‐substituted aromatics with high regioselectivities respectively. Besides, the semi‐intermolecular [2+2+2] cycloaddition between diynes and alkynes are also amenable under this catalytic system. This approach operates without metal reductant, exhibits wide functional groups tolerance, ease of scalability and furnishes 75 examples with moderate to good yields, including some biorelevant compounds. Mechanistic experiments and DFT calculation revealed the catalytic pathways of 1,3,5‐ and 1,2,4‐cyclotrimerizations, and the origin of the ligand controlled regioselectivity.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"56 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745093","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 Selective 1,2‐Thiocyanato‐Imination of Alkenes
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-01 DOI: 10.1002/adsc.202500277
Yu-Shi Jiang, Shan-Shan Li, Yu Lv, Di-Jing Luo, Lu-Lu Qin, Peng-Ju Xia
{"title":"Photocatalytic Selective 1,2‐Thiocyanato‐Imination of Alkenes","authors":"Yu-Shi Jiang, Shan-Shan Li, Yu Lv, Di-Jing Luo, Lu-Lu Qin, Peng-Ju Xia","doi":"10.1002/adsc.202500277","DOIUrl":"https://doi.org/10.1002/adsc.202500277","url":null,"abstract":"A photoinduced energy transfer strategy has been developed for the direct 1,2‐thiocyanato‐imination of alkenes using N‐SCN reagents. The methodology facilitates the synthesis of β‐aminothiocyanates through N‐S bond cleavage, with over 30 examples exhibiting yields up to 88%. Mechanistic studies reveal a radical pathway involving the generation of thiocyanate and iminyl radical species. The resulting β‐aminothiocyanate serves as valuable building blocks for diverse transformations, particularly in the construction of SCN‐containing bioactive molecules with potential pharmaceutical applications.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"3 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745124","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
Titanium‐Free N‐Sulfinyl Ketimine Formation by Transimination
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-01 DOI: 10.1002/adsc.202500178
Kelton Forson, Nicole Sassu, Mariusz Krawiec, Jonathan Reeves
{"title":"Titanium‐Free N‐Sulfinyl Ketimine Formation by Transimination","authors":"Kelton Forson, Nicole Sassu, Mariusz Krawiec, Jonathan Reeves","doi":"10.1002/adsc.202500178","DOIUrl":"https://doi.org/10.1002/adsc.202500178","url":null,"abstract":"Reaction of sulfinamides with in situ generated N‐trifluoromethanesulfonyl ketimines occurs rapidly at room temperature in the presence of KOt‐Bu. The precursor N‐H imines are accessible by organolithium addition to nitriles or condensation of HMDS with ketones. This protocol avoids work‐up and reactor cleaning challenges encountered in the traditional Ti(OEt)4 mediated condensation approach. The reaction works well for extremely hindered substrates, some of which were inaccessible with the Ti(OEt)4 procedure.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"38 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745027","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
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-03-27 DOI: 10.1002/adsc.202401458
Fernando Auria-Luna, María Eugenia Marqués López, M. Concepción Gimeno, Juan V. Alegre-Requena, Raquel Herrera
{"title":"Understanding Chiral Proton Catalysis using Cinchonium Derivatives in aza‐Michael Additions","authors":"Fernando Auria-Luna, María Eugenia Marqués López, M. Concepción Gimeno, Juan V. Alegre-Requena, Raquel Herrera","doi":"10.1002/adsc.202401458","DOIUrl":"https://doi.org/10.1002/adsc.202401458","url":null,"abstract":"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 R 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.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"94 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-03-27","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
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-03-27 DOI: 10.1002/adsc.202500198
Xiyuan Zhang, Bo Jiang, 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, Bo Jiang, Yang Yang, Rui Dong, Jiapeng Ding, Zhiwei Miao","doi":"10.1002/adsc.202500198","DOIUrl":"https://doi.org/10.1002/adsc.202500198","url":null,"abstract":"Abstract. 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.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"100 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-03-27","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‐initiated silylation cyclization of alkynes to access diverse silylated fused cycles
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-03-27 DOI: 10.1002/adsc.202500245
Changyou Guo, Jingyi Chen, Lijun Li, Xin Gu, Qinqin Yan, Kai Sun, Zejiang Li
{"title":"Visible light‐initiated silylation cyclization of alkynes to access diverse silylated fused cycles","authors":"Changyou Guo, Jingyi Chen, Lijun Li, Xin Gu, Qinqin Yan, Kai Sun, Zejiang Li","doi":"10.1002/adsc.202500245","DOIUrl":"https://doi.org/10.1002/adsc.202500245","url":null,"abstract":"Photo‐induced radical silylation cyclization of N‐propargylindoles/(3‐phenoxyprop‐1‐yn‐1‐yl)benzenes with silylboronates or tris(trimethylsilyl)silane was finished, which gave diverse silylated fused cycles. This cascade system featured simple/mild conditions, and good substrate scopes/yields. Meanwhile, a range of scaled‐up experiments, preparation of one silylated active molecule, and mechanistic exploration were performed to examine the application and reaction process.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"19 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143713284","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
Difunctionalization of Glycals and their Derivatives: Strategies and Applications in the Synthesis of Bioactive Compounds
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-03-27 DOI: 10.1002/adsc.202401517
Mittali Maheshwari, Nazar Hussain
{"title":"Difunctionalization of Glycals and their Derivatives: Strategies and Applications in the Synthesis of Bioactive Compounds","authors":"Mittali Maheshwari, Nazar Hussain","doi":"10.1002/adsc.202401517","DOIUrl":"https://doi.org/10.1002/adsc.202401517","url":null,"abstract":"Glycals serve as crucial donor molecules in the synthesis of biologically active compounds. These moieties can undergo functionalization at various positions, such as C‐1, C‐2, and di‐functionalization at multiple sites, including 1,2‐difunctionalization, 2,3‐difunctionalization, and 1,3‐difunctionalization. Among these, 1,2‐difunctionalization can be achieved using diverse methodologies, including metal‐catalyzed reactions, cyclopropane ring opening, epoxide ring opening, and more. Additionally, glycals can be converted into dihalogenated compounds through simple and efficient protocols.Moreover, the 1,3‐difunctionalization process typically involves glycosylation at the anomeric position, followed by the attack of a suitable acceptor. These transformations have proven instrumental in synthesizing various medicinally significant molecules, such as restricticin, SGLT‐2 inhibitors, bergenin, papulacandins A‐D, and tricyclic flavonoids. This review provides an overview of the diverse strategies employed for the difunctionalization of glycals and highlights their application in synthesizing difunctionalized natural products.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"61 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143713286","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(II) complex dispersed in imidazolium‐based ionic liquid: Recyclable catalyst system for regioselective and chemoselective hydrobromination and hydrochlorination of alkynes
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-03-27 DOI: 10.1002/adsc.202401597
min-tsang hsieh, Der-Yen Lee, Yi-Ting Chiang, Hui-Chang Lin
{"title":"Copper(II) complex dispersed in imidazolium‐based ionic liquid: Recyclable catalyst system for regioselective and chemoselective hydrobromination and hydrochlorination of alkynes","authors":"min-tsang hsieh, Der-Yen Lee, Yi-Ting Chiang, Hui-Chang Lin","doi":"10.1002/adsc.202401597","DOIUrl":"https://doi.org/10.1002/adsc.202401597","url":null,"abstract":"We report a recyclable catalyst system combining Cu(II)O and 4,7‐dimethoxy‐1,10‐phenanthroline in a 1‐ethyl‐3‐methylimidazolium‐based ionic liquid for the hydrohalogenation of alkynes. The reaction efficiently yields alkenyl bromides and chlorides with good functional group tolerance and regioselectivity across a range of functionalized alkynes. Remarkably, the reaction exhibits unprecedented chemoselectivity for alkyne over alkenes in polyenynes and enables late‐stage modifications to rapidly synthesize brominated polyenes. The catalyst system could be recycled for up to six runs without significant reduction of the reaction yield.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"12 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143713282","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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