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Advanced Synthesis & Catalysis最新文献

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Synthesis of Vinyl Sulfones and Benzoxathiins via Base‐Catalyzed Reactions of o‐Hydroxyaryl Thiosulfonates and Ynones 通过邻羟基芳基硫代磺酸盐和炔酮的碱催化反应合成乙烯基砜和苯并氧硫杂环胺
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202400456
Delin Tang , Fang Zhang , Jinyun Luo , Zhihua Cai , Lin He , Guangfen Du
{"title":"Synthesis of Vinyl Sulfones and Benzoxathiins via Base‐Catalyzed Reactions of o‐Hydroxyaryl Thiosulfonates and Ynones","authors":"Delin Tang ,&nbsp;Fang Zhang ,&nbsp;Jinyun Luo ,&nbsp;Zhihua Cai ,&nbsp;Lin He ,&nbsp;Guangfen Du","doi":"10.1002/adsc.202400456","DOIUrl":"10.1002/adsc.202400456","url":null,"abstract":"<div><div>The cyclization reaction and hydrosulfonylation reaction of ynones have been simultaneously realized through a single operation. Under the mediation of cesium carbonate, different <em>S</em>‐(<em>α</em>‐hydroxyaryl) aryl thiosulfonates reacted with various ynones to produce functionalized vinyl sulfones in 37%–83% yields with <em>E</em>‐selectivity. At the same time, a variety of benzoxathiins were formed in 42%–97% yields.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202400456"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142374469","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 Tetrahydro‐β‐carbolines via Cascade Sigmatropic Rearrangements 通过级联西格玛式重排合成四氢-β-羰基化合物
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401189
Daiki Oka , Tomomi Ohtsuka , Ken‐ichi Takao , Akihiro Ogura
{"title":"Synthesis of Tetrahydro‐β‐carbolines via Cascade Sigmatropic Rearrangements","authors":"Daiki Oka ,&nbsp;Tomomi Ohtsuka ,&nbsp;Ken‐ichi Takao ,&nbsp;Akihiro Ogura","doi":"10.1002/adsc.202401189","DOIUrl":"10.1002/adsc.202401189","url":null,"abstract":"<div><div>We have developed a synthesis for tetrahydro‐β‐carbolines involving cascade sigmatropic rearrangements. The substrates were conveniently prepared from parent anilines via a [2,3]‐sigmatropic rearrangement and cyanomethylation. Silver‐mediated decyanation afforded the corresponding iminium cation, which underwent a cascade consisting of an aza‐Cope rearrangement, an aza‐oxa‐Cope rearrangement, an aromatization, and a Pictet‐Spengler reaction, and tetrahydro‐β‐carbolines were obtained as the single product. The reaction involved seven bond scissions and four bond formations and was triggered by a single reagent.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202401189"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202401189","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142609892","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 Denitrative C2‐Arylation of Oxazoles, Benzoxazoles, and Benzimidazoles with Nitroarenes pd催化恶唑、苯并恶唑和苯并咪唑与硝基芳烃的c2 -芳基化反应
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401332
Lin Feng , Haiyan Li , Lei Huang , Jiaxin Yao , Wengui Duan , Lin Yu
{"title":"Pd‐Catalyzed Denitrative C2‐Arylation of Oxazoles, Benzoxazoles, and Benzimidazoles with Nitroarenes","authors":"Lin Feng ,&nbsp;Haiyan Li ,&nbsp;Lei Huang ,&nbsp;Jiaxin Yao ,&nbsp;Wengui Duan ,&nbsp;Lin Yu","doi":"10.1002/adsc.202401332","DOIUrl":"10.1002/adsc.202401332","url":null,"abstract":"<div><div>A step‐economic method for C2‐arylated azoles via Pd‐catalyzed denitrative arylation of nitroarenes and azoles is reported. This protocol employs synthetically upstream nitroarenes as arylating reagents and proceeds through the selective cleavage of the C−NO<sub>2</sub> and C−H bonds. Various nitroarenes and nitroheteroarenes were coupled with oxazoles, benzoxazoles, and methylbenzimidazoles, achieving yields of up to 95%. The method's utility is exemplified by its application in the synthesis of Flunoxaprofen. This strategy reduces synthetic steps and minimizes pollution, offering substantial cost‐effectiveness and environmental benefits. Furthermore, the relatively inert C−NO<sub>2</sub> bond in nitroarenes enables late‐stage functionalization or stepwise coupling reactions, providing a complementary method for C2‐arylation of azoles.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202401332"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142753420","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 [4+3] Cycloadditions of N‐Thioacylimines with α‐Chlorohydroxamates: Construction of 1,3,5‐Thiadiazepin‐6(7H)‐One Derivatives n-硫酰基与α-氯羟酸酯的碱促进[4+3]环加成：1,3,5-噻二氮平-6(7H)- 1衍生物的构建
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401193
Yu‐Di Liu , Yu‐Heng Shao , Zhao‐Lin He , Gang Wang
{"title":"Base‐Promoted [4+3] Cycloadditions of N‐Thioacylimines with α‐Chlorohydroxamates: Construction of 1,3,5‐Thiadiazepin‐6(7H)‐One Derivatives","authors":"Yu‐Di Liu ,&nbsp;Yu‐Heng Shao ,&nbsp;Zhao‐Lin He ,&nbsp;Gang Wang","doi":"10.1002/adsc.202401193","DOIUrl":"10.1002/adsc.202401193","url":null,"abstract":"<div><div>A metal‐free base‐promoted [4+3] cycloaddition reaction of <em>N</em>‐thioacyl imines in situ generated from α‐amido sulfones with α‐chlorohydroxamates is described. The reaction allows the straightforward synthesis of 1,3,5‐thiadiazepin‐6(7<em>H</em>)‐one derivatives in 44~90% yields. Moreover, a gram‐scale reaction and a product transformation were conducted, which further increased the diversity of products.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202401193"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142753428","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
DMSO/SOCl2‐Mediated Synthesis of Thiomethylnaphthalenes from Propargyl Alcohols DMSO/SOCl2 介导的原炔醇硫代甲基萘合成反应
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401025
Zhihua Wang , Wang‐Fu Liang , Xinglei He , Jingheng Li , Ke‐Yin Ye
{"title":"DMSO/SOCl2‐Mediated Synthesis of Thiomethylnaphthalenes from Propargyl Alcohols","authors":"Zhihua Wang ,&nbsp;Wang‐Fu Liang ,&nbsp;Xinglei He ,&nbsp;Jingheng Li ,&nbsp;Ke‐Yin Ye","doi":"10.1002/adsc.202401025","DOIUrl":"10.1002/adsc.202401025","url":null,"abstract":"<div><div>Herein, we reported the straightforward synthesis of thiomethylnaphthalenes <em>via</em> the reaction of propargyl alcohols with dimethyl sulfoxide/thionyl chloride (DMSO/SOCl<sub>2</sub>), which also provided easy access to deuterated thiomethyl and other thioalkyl scaffolds when deuterated dimethyl sulfoxide and dialkyl sulfoxides were used, respectively. In addition, the thiomethyl group can be readily derivatized to the corresponding sulfoxide, sulfone, and sulfoximine of interesting photophysical properties.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202401025"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142385450","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‐Induced Stereoselective C(sp3)−C(sp3)−H Glycosylation for the Synthesis of C‐Glycoamino Acid Derivatives 可见光诱导的立体选择性 C(sp3)-C(sp3)-H 糖基化合成 C-氨基乙酸衍生物
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202400875
Guanghui Lv , Pingping Ruan , Hui Sun , Yafei Zhu , Mi Wang , Cuimei Zhang , Jian Chen , Li Guo , Yong Wu
{"title":"Visible‐Light‐Induced Stereoselective C(sp3)−C(sp3)−H Glycosylation for the Synthesis of C‐Glycoamino Acid Derivatives","authors":"Guanghui Lv ,&nbsp;Pingping Ruan ,&nbsp;Hui Sun ,&nbsp;Yafei Zhu ,&nbsp;Mi Wang ,&nbsp;Cuimei Zhang ,&nbsp;Jian Chen ,&nbsp;Li Guo ,&nbsp;Yong Wu","doi":"10.1002/adsc.202400875","DOIUrl":"10.1002/adsc.202400875","url":null,"abstract":"<div><div>Chiral C‐Glycosyl amino acids are prevalent structural motifs found in pharmaceuticals and natural products, making them a significant dimension for exploration in modern pharmaceutical and medicinal chemistry. However, the current synthesis methods for these compounds face numerous environmental and practical challenges, highlighting the critical need to establish more sustainable approaches. Herein, we report a simple and powerful strategy for the stereoselective synthesis of C‐glycoamino acids derivatives. This method features the design and use of (−)/(+)‐camphorsultam as an ideal chiral auxiliary, shielding one prochiral face of the glycine α‐carbon efficiently and imposing a high kinetic barrier for the epimerization of thus‐generated chiral α‐carbon that two configuration products of R and S could be achieved independently. It proceeds under mild conditions, shows broad scope, and allows for the direct stereoselective glycosylation without metal and chiral ligand.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202400875"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142317227","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 Silylation of Aryl Alkynoates: Synthesis of Silylated Coumarins 芳基炔酸盐的光催化硅烷化：硅烷化香豆素的合成
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401007
Ravikumar Ladumor , Sourav Samanta , Sermadurai Selvakumar
{"title":"Photocatalytic Silylation of Aryl Alkynoates: Synthesis of Silylated Coumarins","authors":"Ravikumar Ladumor ,&nbsp;Sourav Samanta ,&nbsp;Sermadurai Selvakumar","doi":"10.1002/adsc.202401007","DOIUrl":"10.1002/adsc.202401007","url":null,"abstract":"<div><div>Herein, we report the photocatalytic synthesis of 3‐silyl coumarins using hydrosilanes as the silyl radical source with aryl alkynoates. Readily prepared <em>N</em>‐aminopyridinium salts act as hydrogen atom transfer reagents for generating silyl radicals under photoredox catalysis. The reaction proceeds through a silyl radical addition to alkyne followed by radical cascade cyclization/migration with subsequent oxidation and aromatization to give the desired 3‐silyl coumarins in 34–89% yield.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202401007"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142374472","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 1,2‐Carboimination of Isothiocyanates to Access S‐Substituted Isothioureas via Energy Transfer Catalysis 通过能量转移催化异硫氰酸酯的选择性 1,2-羧化反应获得 S-取代的异硫脲类化合物
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401233
Li‐Ning Chen , Shu‐Nuo Liang , Juan Luo , Dan‐Na Chen , Zhi‐Peng Ye , Peng‐Ju Xia
{"title":"Selective 1,2‐Carboimination of Isothiocyanates to Access S‐Substituted Isothioureas via Energy Transfer Catalysis","authors":"Li‐Ning Chen ,&nbsp;Shu‐Nuo Liang ,&nbsp;Juan Luo ,&nbsp;Dan‐Na Chen ,&nbsp;Zhi‐Peng Ye ,&nbsp;Peng‐Ju Xia","doi":"10.1002/adsc.202401233","DOIUrl":"10.1002/adsc.202401233","url":null,"abstract":"<div><div>Herein, we introduce a novel method for the synthesis of <em>S</em>‐substituted isothiourea compounds via the selective 1,2‐carboimination between oxime esters as bifunctional reagents and the C=S bond of isothiocyanates under visible‐light catalysis. This approach deviates from conventional methods by precisely modulating the substrate electronics to selectively functionalize the C=S bond of isothiocyanates over the C=N bond, eliminating the need for strong bases and high temperatures and bypassing the formation of thiourea intermediates. Consequently, this protocol enables the efficient one‐step synthesis of <em>S</em>‐alkyl isothioureas, with featuring mild reaction conditions, operational simplicity and broad substrate scope.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202401233"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142580000","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
Modular Chiral Bithiophene‐2NO Ligands: Synthesis and Application in Asymmetric Palladium(II)‐Catalysed Friedel‐Crafts Alkylation 模块化手性噻吩-2NO 配体：不对称钯（II）催化的 Friedel-Crafts 烷基化反应中的合成与应用
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401348
Xian‐Qiao Zhu , Wu‐Wu Li , Lin‐Lu Liu , Ke‐Lan Xu , Li‐Jun Peng , Min Zhang , Xiong‐Li Liu , Wen‐Jing Zhang
{"title":"Modular Chiral Bithiophene‐2NO Ligands: Synthesis and Application in Asymmetric Palladium(II)‐Catalysed Friedel‐Crafts Alkylation","authors":"Xian‐Qiao Zhu ,&nbsp;Wu‐Wu Li ,&nbsp;Lin‐Lu Liu ,&nbsp;Ke‐Lan Xu ,&nbsp;Li‐Jun Peng ,&nbsp;Min Zhang ,&nbsp;Xiong‐Li Liu ,&nbsp;Wen‐Jing Zhang","doi":"10.1002/adsc.202401348","DOIUrl":"10.1002/adsc.202401348","url":null,"abstract":"<div><div>The development of privileged thiophene‐type ligand remains highly desirable, owing to the high coordination ability of sulfur atom to most of the soft metals. Herein, a new class of <em>C<sub>2</sub></em>‐symmetric rigid chiral tertiary amine‐derived dioxide ligands with a coordinating bithiophene bridge was developed in a convenient synthetic route with 25–62% overall yields. The bithiophene‐2NO‐palladium(II) catalyst system was generated <em>in situ</em> and found to be highly capable catalyst in the asymmetric Friedel‐Crafts alkylation of indoles. Excellent yields (up to 92%) and high enantioselectivities (up to &gt;99% ee) are obtained for a wide range of substrates under mild conditions. Control experiments and DFT calculations revealed the origins of the enantioselectivity. This represented the first example of chiral thiophene ligands coordinating with soft metal Pd(II) in the asymmetric Friedel‐Crafts alkylation. Experiments revealed that the counteranion is involved in the stereoselectivity‐determining step in this soft palladium(II) catalysis, and the additional NO and thiophene in ligands can act as the second chelation site and thus reduce the amount of free metal ions for suppressing background reaction in the catalytic system.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202401348"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142713064","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
Biomimetic Orthogonal Removal of Arylacyl Protecting Groups from the C-Terminus of Substituted Amino Acids and Oligopeptides via Flavin N(5)-iminium Covalent Adducts
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-03 DOI: 10.1002/adsc.202401556
Tetiana Pavlovska, Martin Havlik, Magdalena Labikova, Radek Cibulka
{"title":"Biomimetic Orthogonal Removal of Arylacyl Protecting Groups from the C-Terminus of Substituted Amino Acids and Oligopeptides via Flavin N(5)-iminium Covalent Adducts","authors":"Tetiana Pavlovska, Martin Havlik, Magdalena Labikova, Radek Cibulka","doi":"10.1002/adsc.202401556","DOIUrl":"https://doi.org/10.1002/adsc.202401556","url":null,"abstract":"Flavin co-factors and other flavin derivatives are traditionally associated with one- or two-electron redox reactions. Flavins also form covalent intermediates with a variety of substrates. While extensive attention has focused on reactions at the C(4a) position of the flavin ring, recent interest has shifted toward the dynamic potential of the N(5) atom. In our study, we demonstrate the formation of artificial flavin N(5)-iminium covalent adducts via nucleophilic attack by enolates derived from arylacyl esters at the flavin N(5) position. This interaction mimics the biosynthesis of ether phospholipids catalysed by alkyl-dihydroxyacetone phosphate synthase via an N(5)-FAD iminium adduct formation and fatty acid release. Accordingly, we developed a method for the selective removal of phenacyl and 2-naphthylacetyl protecting groups from the C-terminus of α-amino acids and di- and tripeptides using biomimetic flavin organocatalysis. Although many approaches are currently available for protection of C-terminus of peptides, their removal often requires harsh conditions, which cause racemization and the loss of optical purity, together with other side reactions. Our method is versatile, mild, orthogonal to most functional and protecting groups and maintains optical purity of α-amino acids. From general point of view, the method signifies the groundbreaking application of the non-canonical reactivity of flavins in organic synthesis.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"77 4 Pt 2 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143083593","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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