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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 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-07 DOI: 10.1002/adsc.202500253
Mei-Ling Yang, Jing-Yi Cao, Ying-Jian Wu, Xiao-Hu 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, Jing-Yi Cao, Ying-Jian Wu, Xiao-Hu Yang, Wen-Chao Yang, Jian-Jun Wang","doi":"10.1002/adsc.202500253","DOIUrl":"https://doi.org/10.1002/adsc.202500253","url":null,"abstract":"This study developed a novel strategy based on visible-light photocatalysis for the construction of 3-chlorobenzo[b]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.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"4 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-07","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
Copper‐Catalyzed α, β‐Enone Allylic Aerobic Oxidation to 1,4‐Enedione 铜催化α， β -烯酮烯丙基有氧氧化生成1,4 -烯二酮
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-07 DOI: 10.1002/adsc.202500221
Chong Luo, Qing Su, Hong-Xia Zhang, Li-Gang Kou, Ya-Ru Gao, Qiong Jia, Yong-Qiang Wang
{"title":"Copper‐Catalyzed α, β‐Enone Allylic Aerobic Oxidation to 1,4‐Enedione","authors":"Chong Luo, Qing Su, Hong-Xia Zhang, Li-Gang Kou, Ya-Ru Gao, Qiong Jia, Yong-Qiang Wang","doi":"10.1002/adsc.202500221","DOIUrl":"https://doi.org/10.1002/adsc.202500221","url":null,"abstract":"A general, efficient and economic copper‐catalyzed α, β‐enones allylic oxidation to 1,4‐enedione has been developed. The protocol only requires a small amount of cheap copper catalyst with air as the sole oxidant. The advantages of the approach are mild reaction conditions, a broad substrate scope, good tolerance of functional groups, and easy experimental operation. The approach has been demonstrated to be compatible for the late‐stage functionalization of drugs and natural products.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"38 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143790087","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
Regiodivergent Reactions of 2‐Alkynyl Aziridines with Grignard Reagents 2-炔基叠氮嘧啶与格氏试剂的区域发散反应
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-01 DOI: 10.1002/adsc.202401311
Wen‐Tao Ji , A‐Nan Ping , Gaosheng Yang , Zhuo Chai
{"title":"Regiodivergent Reactions of 2‐Alkynyl Aziridines with Grignard Reagents","authors":"Wen‐Tao Ji ,&nbsp;A‐Nan Ping ,&nbsp;Gaosheng Yang ,&nbsp;Zhuo Chai","doi":"10.1002/adsc.202401311","DOIUrl":"10.1002/adsc.202401311","url":null,"abstract":"<div><div>Herein, we report regiodivergent nucleophilic attack of Grignard reagents to 2‐alkynyl aziridines. Under the catalysis of a Cu(I)‐diphosphine complex, benzylic Grignard reagents add to the carbon‐carbon triple bond of the aziridines to deliver α‐allenylamines in moderate to excellent yields; the direct addition of the Grignard reagents to the aziridines in the absence of catalyst provided homopropargylic amine derivatives. Both reactions could proceed in highly enantiospecific ways. Further synthetic manipulations of these products enable rapid access to diverse useful heterocyclic molecular scaffolds.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 7","pages":"Article e202401311"},"PeriodicalIF":4.4,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874309","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
Photoredox Hydroacylative Dearomatization of Indoles with Aromatic Carboxylic Acids 吲哚与芳香族羧酸的光氧化还原氢酰化脱芳
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-01 DOI: 10.1002/adsc.202401401
Chuan‐Hua Qu , Lin Zhu , Shan‐Shan Chen , Hong‐Bo Peng , Si‐Si Zhang , Gui‐Ting Song
{"title":"Photoredox Hydroacylative Dearomatization of Indoles with Aromatic Carboxylic Acids","authors":"Chuan‐Hua Qu ,&nbsp;Lin Zhu ,&nbsp;Shan‐Shan Chen ,&nbsp;Hong‐Bo Peng ,&nbsp;Si‐Si Zhang ,&nbsp;Gui‐Ting Song","doi":"10.1002/adsc.202401401","DOIUrl":"10.1002/adsc.202401401","url":null,"abstract":"<div><div>Herein we reported for the first time a photocatalytic dearomative hydroacylation reaction of electron‐deficient indoles with readily available aromatic acids through a phosphoranyl radical‐assisted deoxygenative process. A range of racemic and optically active 2‐acylindoline derivatives were obtained in good yields (up to 94%) with good diastereoselectivity. The synthetic robustness is highlighted by the enantioselective dearomatization of indoles and the late‐stage modification of natural products and pharmaceutical molecules. This protocol features broad substrate scope and mild reaction conditions, providing a reliable entry to developing deoxygenative strategies in dearomatization reactions. Preliminary mechanistic studies and DFT calculations suggest that a Giese‐type radical addition pathway should be involved.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 7","pages":"Article e202401401"},"PeriodicalIF":4.4,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142935630","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 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
Selective Synthesis of 2‐(Indol‐3‐Yl)Phenols via Iodine‐Catalyzed C3‐Arylation of Indoles with Cyclohexanones 碘催化吲哚与环己酮的C3 -芳基化选择性合成2 -（吲哚- 3 -基）苯酚
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-01 DOI: 10.1002/adsc.202401507
Qi Yin , Xinlin Zhou , Chao Zhang , Shanping Chen , Yuxia Li , Guo‐Jun Deng
{"title":"Selective Synthesis of 2‐(Indol‐3‐Yl)Phenols via Iodine‐Catalyzed C3‐Arylation of Indoles with Cyclohexanones","authors":"Qi Yin ,&nbsp;Xinlin Zhou ,&nbsp;Chao Zhang ,&nbsp;Shanping Chen ,&nbsp;Yuxia Li ,&nbsp;Guo‐Jun Deng","doi":"10.1002/adsc.202401507","DOIUrl":"10.1002/adsc.202401507","url":null,"abstract":"<div><div>An iodine‐catalyzed C3‐arylation of indoles with cyclohexanones to selectively synthesize 2‐(indol‐3‐yl)phenols has been described. Mechanism studies indicate that the oxygen atom in 2‐(indol‐3‐yl)phenols is originally from DMSO. This cascade involving dehydration condensation, selective oxygenation, dehydrogenation, and aromatization was achieved in one pot under transition‐metal‐free conditions.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 7","pages":"Article e202401507"},"PeriodicalIF":4.4,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142961628","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
Catalytic γ‐Position‐Selective Reactions of (2‐Oxopropyl)phosphonates with Aldehydes to Afford γ,δ‐Unsaturated β‐Ketophosphonates （2-氧丙基）膦酸盐与醛的催化γ-位置选择反应生成γ，δ-不饱和β-酮膦酸盐
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-01 DOI: 10.1002/adsc.202401375
James Osborne , Fujie Tanaka
{"title":"Catalytic γ‐Position‐Selective Reactions of (2‐Oxopropyl)phosphonates with Aldehydes to Afford γ,δ‐Unsaturated β‐Ketophosphonates","authors":"James Osborne ,&nbsp;Fujie Tanaka","doi":"10.1002/adsc.202401375","DOIUrl":"10.1002/adsc.202401375","url":null,"abstract":"<div><div>Catalytic formal aldol condensation reactions between β‐ketophosphonates and arylaldehydes, in which the C−C double bond formation occurs at the γ‐position of the β‐ketophosphonate, are reported. The reactions were performed in the presence of a catalyst system composed of <em>p</em>‐anisidine and trifluoroacetic acid under mild conditions. Mechanistic investigations suggest that a Mannich reaction followed by elimination results in the formation of the γ,δ‐unsaturated β‐ketophosphonate. Although the β‐ketophosphonate has an active methylene group, the bond formation occurred selectively at the γ‐position of the β‐ketophosphonate.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 7","pages":"Article e202401375"},"PeriodicalIF":4.4,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202401375","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143495757","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
Disclosing the Intra‐Catalyst Non‐Covalent Interactions in Tetrahydropyran‐Based Dipeptidic Catalysts 揭示了四氢吡喃基二肽催化剂的催化内非共价相互作用
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-01 DOI: 10.1002/adsc.202401443
Irma García‐Monzón , Jorge Borges‐González , Ezequiel Q. Morales , Israel Fernández , Tomás Martín
{"title":"Disclosing the Intra‐Catalyst Non‐Covalent Interactions in Tetrahydropyran‐Based Dipeptidic Catalysts","authors":"Irma García‐Monzón ,&nbsp;Jorge Borges‐González ,&nbsp;Ezequiel Q. Morales ,&nbsp;Israel Fernández ,&nbsp;Tomás Martín","doi":"10.1002/adsc.202401443","DOIUrl":"10.1002/adsc.202401443","url":null,"abstract":"<div><div>Herein, we describe how minor structural modifications to our bifunctional organocatalysts based on sugar amino acids (SAAs) can alter the network of non‐covalent interactions (NCIs) within the catalyst, leading to significant changes in their catalytic activity. This is attributed to the intra‐catalyst NCIs, which induce conformational changes that are reflected in the transition state of the rate‐determining step of the Michael addition of aldehydes to <em>trans</em>‐β‐nitrostyrenes. Through kinetic experiments, conformational analysis, and DFT calculations, we found that the presence of a methoxy group at the C4 position of the tetrahydropyran ring reduces the catalytic activity by a factor of five compared to the catalyst without the methoxy group. Additionally, we have identified the different intra‐catalyst NCIs, both attractive and repulsive, that drive the conformational changes, ultimately modifying the energy levels of the transition states of the rate‐ and enantioselectivity‐determining step of the reaction.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 7","pages":"Article e202401443"},"PeriodicalIF":4.4,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142937429","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 Bishomocubanone Derivatives via Visible‐Light‐Induced Intramolecular [2+2] Cycloaddition Reaction 可见光诱导分子内[2+2]环加成反应合成双叔环醌衍生物
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-01 DOI: 10.1002/adsc.202401345
Bingning Yan , Qingzhong Zhang , Yifei Ling , Jiaxin Liu , Jun Yang
{"title":"Synthesis of Bishomocubanone Derivatives via Visible‐Light‐Induced Intramolecular [2+2] Cycloaddition Reaction","authors":"Bingning Yan ,&nbsp;Qingzhong Zhang ,&nbsp;Yifei Ling ,&nbsp;Jiaxin Liu ,&nbsp;Jun Yang","doi":"10.1002/adsc.202401345","DOIUrl":"10.1002/adsc.202401345","url":null,"abstract":"<div><div>In this paper, a visible‐light‐induced intramolecular [2+2] cycloaddition has been revealed to synthesize the bishomocubanone derivatives in moderate to excellent yield under mild conditions. This method demonstrated a broad substrate scope and excellent functional‐group tolerance, affording cubane precursors and a series of bishomocubanones. Meanwhile, a hundred‐gram scale experiment of this method has been employed to synthesize cubane precursors with 98% yield.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 7","pages":"Article e202401345"},"PeriodicalIF":4.4,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874570","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
Organocatalytic Remote Stereocontrolled (4+2) Annulation of 2‐(4H‐Benzo[d][1,3]oxazin‐4‐yl)acrylates with 4‐Methyleneisoxazol‐5(4H)‐Ones 2 - (4H) -苯并[d][1,3]恶嗪- 4 -酰基)丙烯酸酯与4 -亚甲基异恶唑- 5(4H) -酮的有机催化远程立体控制（4+2）环化
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-01 DOI: 10.1002/adsc.202401603
Yan Liu , Xuling Chen , Pengfei Li
{"title":"Organocatalytic Remote Stereocontrolled (4+2) Annulation of 2‐(4H‐Benzo[d][1,3]oxazin‐4‐yl)acrylates with 4‐Methyleneisoxazol‐5(4H)‐Ones","authors":"Yan Liu ,&nbsp;Xuling Chen ,&nbsp;Pengfei Li","doi":"10.1002/adsc.202401603","DOIUrl":"10.1002/adsc.202401603","url":null,"abstract":"<div><div>Despite the formidable challenge of concurrently managing both the regiochemistry and stereochemistry of the process, organocatalytic remote stereocontrol has emerged as an appealing approach to establish stereocenters at specified locations distant from reactive functional groups. Herein, we achieved the first organocatalyzed remote stereocontrolled (4+2) annulation of 2‐(4<em>H</em>‐benzo[<em>d</em>][1,3]oxazin‐4‐yl)acrylates with 4‐methyleneisoxazol‐5(4<em>H</em>)‐ones. The nucleophilic attack of a suitable chiral amine to 2‐(4<em>H</em>‐benzo[<em>d</em>][1,3]oxazin‐4‐yl)acrylates generated the key amine‐dipole intermediate, followed by the enantioselective aza‐1,4‐addition of 4‐methyleneisoxazol‐5(4<em>H</em>)‐ones and intramolecular annulation cascade reaction to construct spiro[isoxazole‐4,3’‐quinolin]‐5‐one frameworks bearing continuous three stereocenters. More importantly, different from the well‐established reactions of MBH carbonates, this work successfully established a novel platform for the direct enantioselective synthesis of continuous three stereocenters, inclusive of an ϵ‐stereocenter.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 7","pages":"Article e202401603"},"PeriodicalIF":4.4,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462929","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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