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Recent Advancements in Typical Friedel–Crafts Alkylation Reactions Focused on Targeting Arene Nucleophiles 以芳烃亲核试剂为靶点的典型Friedel-Crafts烷基化反应研究进展
4区 化学
Synthesis-Stuttgart Pub Date : 2023-10-02 DOI: 10.1055/s-0042-1751492
Chinmoy K. Hazra, Sanjay Singh
{"title":"Recent Advancements in Typical Friedel–Crafts Alkylation Reactions Focused on Targeting Arene Nucleophiles","authors":"Chinmoy K. Hazra, Sanjay Singh","doi":"10.1055/s-0042-1751492","DOIUrl":"https://doi.org/10.1055/s-0042-1751492","url":null,"abstract":"Abstract This review delves into recent advances and significant breakthroughs in the field of the catalytic Friedel–Crafts alkylation of targeted arenes or heteroarenes. Though a few earlier literatures are referenced, the main emphasis of this review focuses on the literature mainly published between 2015 and March 2023. 1 Introduction 2 History and Background 3 Alcohols as Alkylating Agents 4 Aldehydes and Ketones as Alkylating Agents 5 Alkyl Fluorides as Alkylating Agents 6 Epoxides as Alkylating Agents 7 Cyclopropanes as Alkylating Agents 8 Conclusion and Outlook","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"30 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135828403","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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: 2
Discovery of divergent, light-controlled catalysis triggered by ligand photodissociation from cobalt complexes 发现由钴配合物的配体光解引发的发散性、光控催化
4区 化学
Synthesis-Stuttgart Pub Date : 2023-09-28 DOI: 10.1055/a-2183-4332
Nikita Vystavkin, Manuel Barday, Christopher Teskey
{"title":"Discovery of divergent, light-controlled catalysis triggered by ligand photodissociation from cobalt complexes","authors":"Nikita Vystavkin, Manuel Barday, Christopher Teskey","doi":"10.1055/a-2183-4332","DOIUrl":"https://doi.org/10.1055/a-2183-4332","url":null,"abstract":"Abstract Photochemistry has become a key area of research in synthetic chemistry over the last few decades. More recently, interest has grown in merging this area with transition metal catalysis to develop new reactivity. One key photoinduced step in this context is ligand dissociation from transition metal complexes. This has been used to develop light-gated catalysis, allowing for on/off control over a reaction. However, this concept can only result in a single product outcome. Our group has focused on the development of cobalt-catalyzed reactivity switches, enabled by a simple photodissociation step, which promotes one mechanistic path or another. As such, we can use a single catalytic platform to yield two different outcomes depending on whether the reaction is irradiated with light or not. This short review will focus on works in this area by our group and others. 1 Introduction 2 Photocontrolled Hydroboration 3 Hydrogenation and Hydroformylation 4 Conclusion","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"29 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135385526","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Expedient synthesis of superarmed glycosyl donors via oxidative thioglycosidation of glycals 通过糖基氧化巯基糖化的超臂糖基供体的方便合成
4区 化学
Synthesis-Stuttgart Pub Date : 2023-09-27 DOI: 10.1055/a-2183-0175
Nicholas Forsythe, Emma Mize, Gustavo Kashiwagi, Alexei V Demchenko
{"title":"Expedient synthesis of superarmed glycosyl donors via oxidative thioglycosidation of glycals","authors":"Nicholas Forsythe, Emma Mize, Gustavo Kashiwagi, Alexei V Demchenko","doi":"10.1055/a-2183-0175","DOIUrl":"https://doi.org/10.1055/a-2183-0175","url":null,"abstract":"Abstract Superarmed glycosyl donors have higher reactivity compared to their perbenzylated armed counterparts. Generally, the 2-O-benzoyl-3,4,6-tri-O-benzyl protecting group pattern gives rise to increased reactivity due to an O-2/O-5 cooperative effect. Despite having a high reactivity profile and applicability in many expeditious strategies for glycan synthesis, regioselective introduction of the superarming protecting group pattern is tedious for most sugar series. Reported herein is a streamlined synthetic route to yield superarmed glycosyl donors of the d-gluco and d-galacto series equipped with an ethylthio, phenylthio, p-tolylthio, benzoxazol-2-ylthio, O-allyl, or O-pentenyl anomeric leaving group. This streamlined approach was made possible due to the refinement of the oxidative thioglycosylation reaction of the respective glucal and galactal precursors. The applicability of this approach to the direct formation of disaccharides is also showcased.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"100 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135534669","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 alkylation of diazines with N-(acyloxy)phthalimides in the presence of triethylamine 三乙胺存在下氮杂嗪与N-(酰基)邻苯二胺的光诱导烷基化反应
4区 化学
Synthesis-Stuttgart Pub Date : 2023-09-27 DOI: 10.1055/a-2182-7416
Itziar Guerrero, Eugene Yew Kun Tan, Yuliang Liu, Lee J. Edwards, Shunsuke Chiba
{"title":"Photoinduced alkylation of diazines with N-(acyloxy)phthalimides in the presence of triethylamine","authors":"Itziar Guerrero, Eugene Yew Kun Tan, Yuliang Liu, Lee J. Edwards, Shunsuke Chiba","doi":"10.1055/a-2182-7416","DOIUrl":"https://doi.org/10.1055/a-2182-7416","url":null,"abstract":"Abstract A photochemical protocol for the alkylation of diazines (pyrimidines, pyrazines, and pyridazines) with N-(acyloxy)phthalimides has been developed. The process is facilitated by the presence of triethylamine under irradiation with 427–390 nm light; this enables rapid cross-coupling reactions to construct a wide range of alkylated diazines.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"24 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135478497","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Novel Synthesis of Pyrido[2,3-b]quinoxaline-3-carboxylate Derivatives via One-pot Buchwald Amination-Cyclization 一锅Buchwald胺化法合成吡啶[2,3-b]喹啉-3-羧酸衍生物的新方法
4区 化学
Synthesis-Stuttgart Pub Date : 2023-09-27 DOI: 10.1055/a-2183-0324
majdi Hajiri, Omar Khoumeri, Raoudha Abderrahim, Thierry Terme, Patrice Vanelle
{"title":"Novel Synthesis of Pyrido[2,3-b]quinoxaline-3-carboxylate Derivatives via One-pot Buchwald Amination-Cyclization","authors":"majdi Hajiri, Omar Khoumeri, Raoudha Abderrahim, Thierry Terme, Patrice Vanelle","doi":"10.1055/a-2183-0324","DOIUrl":"https://doi.org/10.1055/a-2183-0324","url":null,"abstract":"Abstract A novel series of pyrido[2,3-b]quinoxaline-3-carboxylate derivatives was synthesized in short reaction times and in moderate to good yields by using a palladium catalyst in a one-pot Buchwald amination/cyclization reaction.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"15 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135534482","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Lewis Acid Catalyzed 4π-Electrocyclization of Donor-Acceptor Stenhouse Adducts Lewis酸催化施-受体斯坦豪斯加合物的4π-电环化
4区 化学
Synthesis-Stuttgart Pub Date : 2023-09-27 DOI: 10.1055/a-2182-9098
Seung Hyeon Yoon, Kye Sung Park, Jaehee Kim, Yonghoon Kwon
{"title":"Lewis Acid Catalyzed 4π-Electrocyclization of Donor-Acceptor Stenhouse Adducts","authors":"Seung Hyeon Yoon, Kye Sung Park, Jaehee Kim, Yonghoon Kwon","doi":"10.1055/a-2182-9098","DOIUrl":"https://doi.org/10.1055/a-2182-9098","url":null,"abstract":"Abstract Lewis acid catalyzed 4π-electrocyclization of Donor–Acceptor Stenhouse Adducts (DASAs) has been developed. By employing catalytic quantities of Dy(OTf)3, a highly efficient transformation of acyclic DASAs into the corresponding cyclized isomers was achieved. Notably, this transformation exhibited exceptional yields, particularly in the case of first generation DASAs. In addition, Lewis acid catalysis enabled one-pot synthesis of the cyclopentenone product from the ‘donor’ and ‘acceptor’ components.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"44 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135478503","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Photo-Induced Electrophilic Aromatic Substitution of Ferric Acyl Nitrene 光诱导三酰基亚硝基铁的亲电芳香取代
4区 化学
Synthesis-Stuttgart Pub Date : 2023-09-27 DOI: 10.1055/a-2183-0262
Ming Hou, Zhide Zhang, Xiaojing Lai, Qianzhou Zong, Miaofeng Ren, Tianwen Bai, Guanyinsheng Qiu
{"title":"Photo-Induced Electrophilic Aromatic Substitution of Ferric Acyl Nitrene","authors":"Ming Hou, Zhide Zhang, Xiaojing Lai, Qianzhou Zong, Miaofeng Ren, Tianwen Bai, Guanyinsheng Qiu","doi":"10.1055/a-2183-0262","DOIUrl":"https://doi.org/10.1055/a-2183-0262","url":null,"abstract":"A photo-induced intramolecular electron-aromatic-substitution (SEAr) of N-acyloxybenzozmide under 20 mol% FeCl3 at 1, 4-dioxane is reported for the synthesis of biologically interesting benzoxazin-3(4H)-ones. In the reaction, it is believed that blue LED facilitates the reaction, like reaction temperature serving as source of energy. The reaction SEAr pathway was ascribed to the electron effect in aryl ring of substrates. The reaction was also applicable for the synthesis of useful scaffolds possessing a quinolin-2-one core, such as anticancer reagent 4, brexipiprazole and cilostamide analogues.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"78 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135534543","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Linked PDF of Table of Contents 链接的PDF目录
4区 化学
Synthesis-Stuttgart Pub Date : 2023-09-27 DOI: 10.1055/s-0040-1720092
{"title":"Linked PDF of Table of Contents","authors":"","doi":"10.1055/s-0040-1720092","DOIUrl":"https://doi.org/10.1055/s-0040-1720092","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"99 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135534825","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Modern Macrolactonization Techniques 现代大内酯化技术
4区 化学
Synthesis-Stuttgart Pub Date : 2023-09-26 DOI: 10.1055/a-2181-9800
Max Van Hoof, Guillaume Force, David Leboeuf
{"title":"Modern Macrolactonization Techniques","authors":"Max Van Hoof, Guillaume Force, David Leboeuf","doi":"10.1055/a-2181-9800","DOIUrl":"https://doi.org/10.1055/a-2181-9800","url":null,"abstract":"Abstract The study of macrolactonization processes has been a steady endeavor for synthetic chemists to access macrocycles that are fundamental in the development of numerous high-added-value compounds, notably drugs and fragrances. This field of research is essential as macrolactonizations usually take place at the end of manifold syntheses and chemists need reliable, efficient, and versatile tools to avoid unpredictable results that would lead them to completely redesign their synthetic plan. Here, we highlight the recent methods reported to achieve macrolactonizations towards the formation of both macrolactones and macrodiolides, which feature either Lewis acids, transition metals or organic molecules as activating agents. 1 Introduction 2 Stoichiometric Carboxylic Acid Activation 3 Lewis Acid Catalyzed Reaction 4 C–H Activation 5 Ring-Expansion Strategy 6 Chemoenzymatic Synthesis 7 Other Macrolactonization Variants 8 Conclusion and Outlook","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"59 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134885383","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
SYNFORM ISSUE 2023/10 Synform issue 2023/10
4区 化学
Synthesis-Stuttgart Pub Date : 2023-09-26 DOI: 10.1055/s-0040-1720611
Matteo Zanda
{"title":"SYNFORM ISSUE 2023/10","authors":"Matteo Zanda","doi":"10.1055/s-0040-1720611","DOIUrl":"https://doi.org/10.1055/s-0040-1720611","url":null,"abstract":"INTERVIEW SYNFORM What is the focus of your current research activities? Prof","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"13 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134885558","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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