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Design of Synthetic Strategies towards Sulfur Containing Scaffolds 设计含硫支架的合成策略
Synthesis Pub Date : 2024-08-28 DOI: 10.1055/s-0043-1775393
Sambasivarao Kotha, Priti Khedkar
{"title":"Design of Synthetic Strategies towards Sulfur Containing Scaffolds","authors":"Sambasivarao Kotha, Priti Khedkar","doi":"10.1055/s-0043-1775393","DOIUrl":"https://doi.org/10.1055/s-0043-1775393","url":null,"abstract":"<p>The utilization of sulfur heterocycles in organic synthesis has attracted significant attention due to their wide-ranging applications. This review showcases the syntheses of diverse sulfur heterocycles embedded with amino acid derivatives, polycycles, spirocycles, cyclophanes, and other complex scaffolds. The reported methods extend beyond compound synthesis and highlight the use of different sulfur reagents for constructing sulfur heterocycles. This Review also discusses the utility of a variety of sulfur-containing starting materials for the generation of complex target molecules.</p> <p>1 Introduction</p> <p>2 Potassium Thioacetate</p> <p>3 Thiazolidine-2,4-dione</p> <p>4 Rhodanines</p> <p>5 Sodium Sulfide</p> <p>6 Thiotetronic Acid</p> <p>7 Thiadiazoles</p> <p>8 Thiophene</p> <p>9 Rongalite</p> <p>10 Sulfur Dioxide</p> <p>11 Divinyl Sulfone</p> <p>12 Sulfur Heterocycles Based on Boronic Acids</p> <p>13 Miscellaneous</p> <p>14 Summary</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207424","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Palladium-Catalyzed γ-C–H Arylation of Unsaturated Carbonyl Compounds: An Emerging Remote Buchwald–Hartwig–Miura Arylation 钯催化不饱和羰基化合物的 γ-C-H 芳基化反应：一种新兴的远程布赫瓦尔德-哈特维格-米乌拉芳基化反应
Synthesis Pub Date : 2024-08-27 DOI: 10.1055/a-2376-3429
Dashan Li, Yan-Ping Peng, Li-Dong Shao
{"title":"Palladium-Catalyzed γ-C–H Arylation of Unsaturated Carbonyl Compounds: An Emerging Remote Buchwald–Hartwig–Miura Arylation","authors":"Dashan Li, Yan-Ping Peng, Li-Dong Shao","doi":"10.1055/a-2376-3429","DOIUrl":"https://doi.org/10.1055/a-2376-3429","url":null,"abstract":"<p>As an important complement to the Buchwald–Hartwig–Miura arylation, Pd-catalyzed γ-C–H arylations, including γ-C(sp<sup>3</sup>)–H and γ-C(sp<sup>2</sup>)–H arylations, provide a more direct route to install an aryl group on the less reactive γ-site of unsaturated carbonyl compounds, and have attracted considerable interest from the chemistry community in recent years. This review summarizes the applications of this method with both cyclic and linear unsaturated carbonyl compounds (aldehydes, ketones, esters, amide, and nitriles), as well as in the total synthesis of natural products (NPs), natural product skeletons, and bioactive analogues.</p> <p>1 Introduction</p> <p>2 γ-C–H Arylation of Cyclic Unsaturated Carbonyl Substrates</p> <p>2.1 Exocyclic γ-Arylation</p> <p>2.1.1 Unsaturated Ketones and the Corresponding Silyl-Dienol Ethers</p> <p>2.1.2 Unsaturated Lactones</p> <p>2.2 Endocyclic γ-C–H Arylation</p> <p>2.2.1 Unsaturated Ketones and the Corresponding Silyl-Dienol Ethers</p> <p>2.2.2 Unsaturated Lactones</p> <p>2.2.3 Unsaturated Nitriles</p> <p>3 γ-C–H Arylation of Linear Unsaturated Carbonyl Substrates</p> <p>3.1 Unsaturated Aldehydes</p> <p>3.2 Unsaturated Ketones</p> <p>3.3 Unsaturated Amides</p> <p>3.4 Unsaturated Nitriles</p> <p>3.5 Silyl Ketene Acetals of α,β-Unsaturated Esters</p> <p>4 Conclusion</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207427","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Solvent-Controlled Divergent Synthesis of Thiocyanated Carbazoles and Di/Triphenylamines 硫氰酸咔唑和二/三苯基胺的溶剂控制分歧合成
Synthesis Pub Date : 2024-08-26 DOI: 10.1055/a-2378-4540
You-Hui Tang, Peng Chen, Jin Yin, Jianghuan Shi, Yi-Jun Jiang
{"title":"Solvent-Controlled Divergent Synthesis of Thiocyanated Carbazoles and Di/Triphenylamines","authors":"You-Hui Tang, Peng Chen, Jin Yin, Jianghuan Shi, Yi-Jun Jiang","doi":"10.1055/a-2378-4540","DOIUrl":"https://doi.org/10.1055/a-2378-4540","url":null,"abstract":"<p>A solvent-controlled divergent thiocyanation of carbazoles and di/triphenylamines has been developed. Using either CH<sub>3</sub>CN/H<sub>2</sub>O (3:1) or DMSO as the solvent, a facile and efficient protocol for the solvent-controlled divergent synthesis of mono- and di-thiocyanation of carbazoles and di/triphenylamines was achieved. The salient features of this transformation include simple and mild reaction conditions, easily available substrates, and broad substrate scope.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207428","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent Advances in Asymmetric Addition Reactions to Isatins 异汀类不对称加成反应的最新进展
Synthesis Pub Date : 2024-08-22 DOI: 10.1055/a-2376-6463
Ke Xie, Ao Li, Bao-Rui Kong, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
{"title":"Recent Advances in Asymmetric Addition Reactions to Isatins","authors":"Ke Xie, Ao Li, Bao-Rui Kong, Zhi-Chao Chen, Wei Du, Ying-Chun Chen","doi":"10.1055/a-2376-6463","DOIUrl":"https://doi.org/10.1055/a-2376-6463","url":null,"abstract":"<p>The 3-substituted-3-hydroxy-2-oxindole scaffolds are not only widely encountered in bioactive compounds but also serve as versatile building blocks for the construction of diverse valuable architectures. Although numerous synthetic methodologies have been developed over the past decades, the asymmetric addition of nucleophiles or their equivalents to isatin substrates has proved to be one of the most efficient strategies for the synthesis of chiral 3-substituted-3-hydroxy-2-oxindoles. This Short Review aims to summarize the significant progress achieved in this field in recent years, with particular attention paid to reaction development, mechanism, and stereo-induction models.</p> <p>1 Introduction</p> <p>2 Asymmetric Alkylation of Isatins</p> <p>3 Asymmetric Alkenylation and Dienylation of Isatins</p> <p>4 Asymmetric Alkynylation of Isatins</p> <p>5 Asymmetric Allenylation of Isatins</p> <p>6 Asymmetric Arylation of Isatins</p> <p>7 Asymmetric Annulations of Isatins</p> <p>8 Conclusions and Outlooks</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207429","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A Comprehensive Approach to C3a-Aryl-Substituted Hydroindole Alkaloids by Utilizing Enantioselective Gold Catalysis 利用对映体选择性金催化生产 C3a-芳基取代的氢吲哚生物碱的综合方法
Synthesis Pub Date : 2024-08-19 DOI: 10.1055/s-0043-1775389
Jhen Kuei Yu, Constantin Czekelius
{"title":"A Comprehensive Approach to C3a-Aryl-Substituted Hydroindole Alkaloids by Utilizing Enantioselective Gold Catalysis","authors":"Jhen Kuei Yu, Constantin Czekelius","doi":"10.1055/s-0043-1775389","DOIUrl":"https://doi.org/10.1055/s-0043-1775389","url":null,"abstract":"<p>A diversity-oriented total synthesis for <i>Amaryllidaceae</i> alkaloids incorporating the frequently found C3a-arylated hydroindole moiety was developed. Chiral-anion-induced gold(I) catalysis was employed for the cyclization of 1,4-diynes to the pyrrolidine and the installation of the all-carbon quaternary stereocenter. Both enantiomeric series of crinine-type alkaloids in high enantiopurity were accessible by this methodology. The formal synthesis of a wide range of <i>Amaryllidaceae</i> alkaloids is described, such as (+)-vitattine, (–)-<i>epi</i>-vitattine, (–)-elwesein, (–)-<i>epi</i>-elwesein, (–)-crinine, (–)-<i>epi</i>-crinine, (–)-buphanisine, (–)-flexinine, and (+)-gracilamine.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-08-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207456","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent Trends in Triarylborane Chemistry: Diversification of Structures and Reactivity via meta-Substitution of the Aryl Groups 三芳基硼烷化学的最新发展趋势：通过芳基的元取代实现结构和反应活性的多样化
Synthesis Pub Date : 2024-08-19 DOI: 10.1055/s-0043-1775394
Mahiro Sakuraba, Yoichi Hoshimoto
{"title":"Recent Trends in Triarylborane Chemistry: Diversification of Structures and Reactivity via meta-Substitution of the Aryl Groups","authors":"Mahiro Sakuraba, Yoichi Hoshimoto","doi":"10.1055/s-0043-1775394","DOIUrl":"https://doi.org/10.1055/s-0043-1775394","url":null,"abstract":"<p>This Short Review summarizes the synthesis and applications of triarylboranes (BAr<sub>3</sub>), including both homoleptic and heteroleptic species, with a focus on the modification of their electronic and structural properties via the introduction of <i>meta</i>-substituents with respect to the B atoms to their Ar groups. This approach constitutes a complementary alternative to conventional strategies for the design of BAr<sub>3</sub>, which are usually based on a modification of their <i>ortho</i>- and/or <i>para</i>-substituents. An initial analysis revealed that CH<sub>3</sub> and F are the most common <i>meta</i>-substituents in hitherto reported BAr<sub>3</sub> (apart from the H atom). Thus, an extensive exploration of other substituents, e.g., heavier halogens, longer or functionalized alkyl groups, and aryl groups, will increase our knowledge of the structure and reactivity of BAr<sub>3</sub> and eventually lead to a range of new applications.</p> <p>1 Introduction</p> <p>2 Scope of this Review</p> <p>2.1 The Electronic and Steric Influence of <i>meta</i>-Substituents</p> <p>2.2 Molecular Transformations Mediated by <i>meta</i>-Substituted Boranes</p> <p>2.3 Other Examples of <i>meta</i>-Functionalization of BAr<sub>3</sub>\u0000</p> <p>3 Conclusions and Perspectives</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-08-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207454","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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 (NHC)-Catalyzed Tail-to-Tail Dimerization of Acrylamides N-Heterocyclic Carbene (NHC) 催化的丙烯酰胺尾对尾二聚化反应
Synthesis Pub Date : 2024-08-14 DOI: 10.1055/s-0043-1775037
Chensheng Zhao, Bingwei Zhou
{"title":"N-Heterocyclic Carbene (NHC)-Catalyzed Tail-to-Tail Dimerization of Acrylamides","authors":"Chensheng Zhao, Bingwei Zhou","doi":"10.1055/s-0043-1775037","DOIUrl":"https://doi.org/10.1055/s-0043-1775037","url":null,"abstract":"<p>The tail-to-tail dimerization of acrylamides enables the formation of diamides. However, only one example of <i>N</i>,<i>N</i>-dimethylacrylamide has been described in the literature. Herein, an NHC-catalyzed tail-to-tail dimerization of acrylamides in moderate to excellent yields is presented. In this context, <i>N</i>-arylacrylamides are susceptible to the dimerization reaction, which features high reaction efficiency, good <i>E</i>-selectivity, and easy operation.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207455","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Catalytic Intermolecular [4+2]-Cycloaddition toward Stereoselective C2-C3 Annulation of Indoles 催化分子间 [4+2]- 环加成实现吲哚的立体选择性 C2-C3 嵌合反应
Synthesis Pub Date : 2024-08-09 DOI: 10.1055/a-2383-7416
Soumen Pandit, N. Majumdar
{"title":"Catalytic Intermolecular [4+2]-Cycloaddition toward Stereoselective C2-C3 Annulation of Indoles","authors":"Soumen Pandit, N. Majumdar","doi":"10.1055/a-2383-7416","DOIUrl":"https://doi.org/10.1055/a-2383-7416","url":null,"abstract":"Catalytic dearomative cycloaddition with C2-C3 bond of indoles is a powerful strategy for the synthesis of fused indoline scaffolds. By dearomative cycloaddition/annulation, planar indole substrates can be readily transformed into rigid, three-dimensional polycyclic complex structures in one step. Architectural complexity of molecules is generally considered as drug-like properties. Thus, the annulation products have tremendous potential in discovering therapeutic properties. This strategy has become an important part of the medicinal chemistry toolbox. Using appropriate catalyst control, desirable stereoselectivity can be achieved in the reaction. Previous literature reports indicate that [3+2]-cycloaddition of indoles has been extensively studied. On the contrary, catalytic [4+2]-cycloaddition/dearomatization of indoles has been much less investigated. In this review, we aim to focus specifically on the six- membered ring annulation via [4+2]-cycloaddition with C2-C3 bond of indoles and discuss on various catalytic methods that have been developed toward this direction.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-08-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141923011","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent advances in the chemistry and the application of SF5-compounds SF5 化合物化学和应用方面的最新进展
Synthesis Pub Date : 2024-08-09 DOI: 10.1055/a-2383-6620
Mariam Abd El Sater, Lucas Popek, Nicolas Blanchard, Vincent Bizet
{"title":"Recent advances in the chemistry and the application of SF5-compounds","authors":"Mariam Abd El Sater, Lucas Popek, Nicolas Blanchard, Vincent Bizet","doi":"10.1055/a-2383-6620","DOIUrl":"https://doi.org/10.1055/a-2383-6620","url":null,"abstract":"This review article outlines the literature covering last three years on the recent developments of the SF5 chemistry. Recent synthesis methodologies of SF5-containing building blocks are reported. These methods include the synthesis of SF5Cl, its use in pentafluorosulfanylation reactions, and oxidative fluorination reactions. Moreover, the reactivity of SF5-alkynes as versatile platform to access new SF5-compounds is described. Finally, effect of SF5 moiety is highlighted according to its application in different fields such as biological/medicinal chemistry, catalysis and material sciences.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-08-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141922441","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis and Reactivity of α-Diazo-β-keto Sulfonamides α-Diazo-β-keto 磺酰胺的合成与反应活性
Synthesis Pub Date : 2024-08-08 DOI: 10.1055/a-2348-5631
Evan R. Judge, Keith O’Shaughnessy, Simon E. Lawrence, Stuart G. Collins, Anita R. Maguire
{"title":"Synthesis and Reactivity of α-Diazo-β-keto Sulfonamides","authors":"Evan R. Judge, Keith O’Shaughnessy, Simon E. Lawrence, Stuart G. Collins, Anita R. Maguire","doi":"10.1055/a-2348-5631","DOIUrl":"https://doi.org/10.1055/a-2348-5631","url":null,"abstract":"<p>Copper-mediated reactions of α-diazo-β-keto sulfonamides led to a range of products, including alkynesulfonamides, enamines, and α-halosulfonamides, with no evidence for intramolecular C–H insertion in any of the reactions, in contrast to the reactivity of the comparable α-diazo-β-oxo sulfones. Use of copper(II) triflate (5 mol%) led to the isolation of a series of alkynesulfonamides (up to 12% yield) and enamines (up to 64% yield). Use of copper(II) chloride (5 mol%) led to the formation, in addition, of α-halosulfonamides; use of stoichiometric amounts of copper(II) chloride/bromide enabled facile halogenation of the β-keto sulfonamide to form α-halosulfonamides (up to 63% yield).</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141932948","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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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