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Chiral Sulfones via Single-Electron Oxidation-Initiated Photoenzymatic Catalysis 通过单电子氧化引发的光酶催化手性砜
IF 2 4区 化学
Synlett Pub Date : 2024-06-18 DOI: 10.1055/s-0043-1775372
Pandaram Sakthivel, Qinglong Shi, Juntao Ye
{"title":"Chiral Sulfones via Single-Electron Oxidation-Initiated Photoenzymatic Catalysis","authors":"Pandaram Sakthivel, Qinglong Shi, Juntao Ye","doi":"10.1055/s-0043-1775372","DOIUrl":"https://doi.org/10.1055/s-0043-1775372","url":null,"abstract":"<p>We recently achieved an oxidation-initiated photoenzymatic enantioselective hydrosulfonylation of olefins through the utilization of a new Gluconobacter ene-reductase mutant (GluER-W100F-W342F). Our method simplifies the reaction system by eliminating the need for a cofactor regeneration mixture and, in contrast with previous photoenzymatic systems, does not depend on the formation of an electron donor–acceptor (EDA) complex between the substrates and enzyme cofactor. Moreover, the GluER variant exhibits good substrate compatibility and excellent enantioselectivity. Mechanistic investigations indicate that a tyrosine-mediated HAT process is involved and support the proposed oxidation-initiated mechanism. In this Synpacts article, we discuss the conceptual framework that led to the discovery of this reaction and reflect on the key aspects of its development.</p> <p>1 Introduction</p> <p>2 Conceptual Background</p> <p>2.1 Intramolecular Photoenzymatic Reactions <i>via</i> Single-Electron Reduction</p> <p>2.2 Intermolecular Photoenzymatic Reactions <i>via</i> Single-Electron Reduction</p> <p>3 The Development of the Process</p> <p>4 Conclusion</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"20 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141522807","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
Ni(OTf)2-Catalyzed Michael Addition Reactions of 4-Hydroxycoumarins to α,β-Unsaturated 2-Acyl Imidazoles Ni(OTf)2 催化的 4-羟基香豆素与 α、β-不饱和 2-酰基咪唑的迈克尔加成反应
IF 2 4区 化学
Synlett Pub Date : 2024-06-14 DOI: 10.1055/a-2310-0924
Honghong Wang, Fan Gong, Ping Xue, Helin Lu, Xiaobo Wang, Jun Gong
{"title":"Ni(OTf)2-Catalyzed Michael Addition Reactions of 4-Hydroxycoumarins to α,β-Unsaturated 2-Acyl Imidazoles","authors":"Honghong Wang, Fan Gong, Ping Xue, Helin Lu, Xiaobo Wang, Jun Gong","doi":"10.1055/a-2310-0924","DOIUrl":"https://doi.org/10.1055/a-2310-0924","url":null,"abstract":"<p>An efficient Michael addition of 4-hydroxycoumarins to α,β-unsaturated 2-acyl imidazoles catalyzed by Ni(OTf)<sub>2</sub> as a Lewis acid has been developed. A series of 4-hydroxycoumarin derivatives were obtained in excellent yields (up to 96%) with a 2 mol% catalyst loading under mild conditions. Additionally, when a chiral-at-metal rhodium complex was used as the catalyst, moderate enantioselectivity was observed (74% ee).</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"72 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141501830","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
Electrosynthesis of Quinoxalines via Intermolecular Cyclization/Dehydrogenation of Ketones with o-Phenylenediamines 通过酮与邻苯二胺的分子间环化/脱氢反应电合成喹喔啉类化合物
IF 2 4区 化学
Synlett Pub Date : 2024-06-14 DOI: 10.1055/a-2339-2832
Yi Tao, Jiahui Zhang, Yangyang Hu, Huiying Liu, Jingwen Sun, Lei Liu
{"title":"Electrosynthesis of Quinoxalines via Intermolecular Cyclization/Dehydrogenation of Ketones with o-Phenylenediamines","authors":"Yi Tao, Jiahui Zhang, Yangyang Hu, Huiying Liu, Jingwen Sun, Lei Liu","doi":"10.1055/a-2339-2832","DOIUrl":"https://doi.org/10.1055/a-2339-2832","url":null,"abstract":"<p>In this study, we proposed a novel electrochemical dehydrogenative synthetic method for preparing 2-substituted quinoxalines by intermolecular cyclization of aryl alkyl ketones and <i>o</i>-phenylenediamines. This method gave various quinoxalines in yields ranging from 35% to 71%. This novel protocol employs mild reaction conditions and offers moderate to excellent yields, a wide substrate scope, and broad functional-group compatibility. Furthermore, a late-stage functionalization and the wide substrate scope demonstrated the synthetic utility of this protocol.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"137 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141522813","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
Nickel-Catalyzed Regio- and Enantioselective Hydrofluorination in Unactivated Alkenes 镍催化未活化烯烃的区域和对映选择性氢氟化反应
IF 2 4区 化学
Synlett Pub Date : 2024-06-13 DOI: 10.1055/a-2334-6568
Minseok Kim, Seunghoon Han, Sungwoo Hong
{"title":"Nickel-Catalyzed Regio- and Enantioselective Hydrofluorination in Unactivated Alkenes","authors":"Minseok Kim, Seunghoon Han, Sungwoo Hong","doi":"10.1055/a-2334-6568","DOIUrl":"https://doi.org/10.1055/a-2334-6568","url":null,"abstract":"<p>While enantioselective hydrofluorination methods for activated alkenes represent a notable advance, the resultant enantiomeric excesses remain largely moderate, indicating the necessity for enhancements in precision, efficiency, and scope. We have recently developed an innovative nickel hydride catalytic system that enables regio- and enantioselective C–F bond formation with unactivated alkenes. By utilizing specially designed Bn-BOx ligands for improved selectivity, our approach demonstrates exceptional efficiency and selectivity with β,γ-alkenyl amide substrates. This breakthrough enhances the synthesis of organofluorine compounds, marking a significant advancement in organic synthesis.</p> <p>1 Introduction</p> <p>2 Reaction Design of Hydrofluorination</p> <p>3 Regio- and Enantioselective Hydrofluorination</p> <p>4 Asymmetric Amplification</p> <p>5 Conclusions</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"15 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141522810","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
Electromediated Alcohol-Based Passerini-Type Reaction 基于酒精的电促进帕塞里尼式反应
IF 2 4区 化学
Synlett Pub Date : 2024-06-12 DOI: 10.1055/a-2333-8596
Alexandre Simon, Sylvestre P. J. T. Bachollet, Na Pan, Laurence Grimaud, Maxime R. Vitale
{"title":"Electromediated Alcohol-Based Passerini-Type Reaction","authors":"Alexandre Simon, Sylvestre P. J. T. Bachollet, Na Pan, Laurence Grimaud, Maxime R. Vitale","doi":"10.1055/a-2333-8596","DOIUrl":"https://doi.org/10.1055/a-2333-8596","url":null,"abstract":"<p>An electrochemical variant of the alcohol-based oxidative Passerini reaction is reported here. It relies on an indirect anodic oxidation process followed by a three-component coupling, in which TEMPO serves as a key redox mediator. This electrochemical approach permits to operate without the need for a metal catalyst nor oxygen atmosphere and allows the use of nonactivated alcohols as reaction partners. It could be applied to the preparation of good variety of α-acyloxy-carboxamides in yields ranging from 24% to 80%.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"48 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141522809","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
Heterogenization of [Ru(bpy)3]Cl2 on Ordered Mesoporous Silica Materials for Photocatalytic Applications 有序介孔二氧化硅材料上的[Ru(py)3]Cl2异质化，用于光催化应用
IF 2 4区 化学
Synlett Pub Date : 2024-06-11 DOI: 10.1055/a-2317-3672
Malik Sebbat, Anish Lazar, Claire Laurent, Christelle Despas, Neus Vilà, Alain Walcarius, Nathan McClenaghan, Emmanuel Oheix, Bénédicte Lebeau, Morgan Cormier, Jean-Philippe Goddard
{"title":"Heterogenization of [Ru(bpy)3]Cl2 on Ordered Mesoporous Silica Materials for Photocatalytic Applications","authors":"Malik Sebbat, Anish Lazar, Claire Laurent, Christelle Despas, Neus Vilà, Alain Walcarius, Nathan McClenaghan, Emmanuel Oheix, Bénédicte Lebeau, Morgan Cormier, Jean-Philippe Goddard","doi":"10.1055/a-2317-3672","DOIUrl":"https://doi.org/10.1055/a-2317-3672","url":null,"abstract":"<p>Herein, the preparation and characterization of three Ru-based heterogeneous photocatalysts supported on ordered mesoporous silica materials are reported. The photocatalytic activity of these catalysts was evaluated through oxidation, reduction, cycloaddition, and carboxylation reactions and their efficiencies are comparable to the parent [Ru(bpy)<sub>3</sub>]Cl<sub>2</sub> under homogeneous conditions. These photocatalysts are efficiently recovered even after five reaction cycles offering new opportunities in sustainable chemistry.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"69 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141501831","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
Construction of Three Novel Oxygen-Containing Cagelike Frameworks and Synthesis of their Energetic Derivatives 构建三种新型含氧类囊体框架并合成其高能衍生物
IF 2 4区 化学
Synlett Pub Date : 2024-06-06 DOI: 10.1055/a-2333-8774
Huan Li, Qi Zhou, Jingjing Zhao, Tianjiao Hou, Guixiang Wang, Long Zhu, Bing Li, Yu Zhang, Jun Luo
{"title":"Construction of Three Novel Oxygen-Containing Cagelike Frameworks and Synthesis of their Energetic Derivatives","authors":"Huan Li, Qi Zhou, Jingjing Zhao, Tianjiao Hou, Guixiang Wang, Long Zhu, Bing Li, Yu Zhang, Jun Luo","doi":"10.1055/a-2333-8774","DOIUrl":"https://doi.org/10.1055/a-2333-8774","url":null,"abstract":"<p>Organic cagelike frameworks are important and versatile skeletons for developing prospective energetic compounds because of their high intrinsic density, symmetry, stability, and derivability. Herein, we show the construction of three novel cagelike frameworks including dioxaadamantane, dioxaproadamantane, and dioxatwistane from 9-oxabicyclo[3.3.1]nonane-2,6-diene. In addition, their energetic derivatives were also prepared and characterized. Compared with our previous works, the introduction of more oxygen atoms into the framework gives the corresponding energetic derivative a better oxygen balance, significantly higher density, and detonation properties. These results imply that the oxygen-containing framework has the potential to be used for preparing new 3D energetic compounds with superior energy performance.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"52 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-06-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141551714","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
Tandem Diboration–Protoboration of Terminal Alkynes: A Practical Route to α-Substituted Alkenyl Boronates 端基炔烃的串联二重化-硼化反应：制备 α-取代烯基硼酸盐的实用途径
IF 2 4区 化学
Synlett Pub Date : 2024-06-05 DOI: 10.1055/s-0043-1774906
Ziyin Kong, Jimin Park, Muchun Fei, Josephine Warfield, Dunwei Wang, James P. Morken
{"title":"Tandem Diboration–Protoboration of Terminal Alkynes: A Practical Route to α-Substituted Alkenyl Boronates","authors":"Ziyin Kong, Jimin Park, Muchun Fei, Josephine Warfield, Dunwei Wang, James P. Morken","doi":"10.1055/s-0043-1774906","DOIUrl":"https://doi.org/10.1055/s-0043-1774906","url":null,"abstract":"<p>A practical method is introduced for the catalytic conversion of terminal alkynes into α-substituted vinyl boronic esters. The process employs catalytic amounts of nanoparticle-supported gold catalysts and catalytic amounts of copper to effect the overall transformation.</p>","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"4 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141522812","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
Visible-Light-Driven Metal-Free and Photocatalyst-Free Intra­molecular Cyclization of Chalcones to Access Phenanthrenes 可见光驱动的无金属和无光催化剂查耳酮分子内环化反应生成菲
IF 2 4区 化学
Synlett Pub Date : 2024-06-05 DOI: 10.1055/a-2315-8320
Miaoyan Yi, Chen Zhang, Saihu Liao, Bing Sun
{"title":"Visible-Light-Driven Metal-Free and Photocatalyst-Free Intra­molecular Cyclization of Chalcones to Access Phenanthrenes","authors":"Miaoyan Yi, Chen Zhang, Saihu Liao, Bing Sun","doi":"10.1055/a-2315-8320","DOIUrl":"https://doi.org/10.1055/a-2315-8320","url":null,"abstract":"<p>We report a visible-light-driven metal-free and photocatalyst-free protocol for the synthesis of phenanthrenes through the intramolecular cyclization of chalcones. The transformation proceeds through light irradiation and base- and oxygen-based promotion, and enables the generation of a series of phenanthrenes. The further functionalization of an as-synthesized phenanthrene to afford a fluorescent molecule was explored.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"6 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141522811","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
His-Tagging: Exploring Precise Chemical Modification of Histidine-Containing Bioactive Peptide Sequences His-Tagging：探索对含组氨酸生物活性肽序列的精确化学修饰
IF 2 4区 化学
Synlett Pub Date : 2024-06-03 DOI: 10.1055/s-0043-1775364
Sourav Chatterjee, Bishwajit Paul, Govindaswamy Shanker
{"title":"His-Tagging: Exploring Precise Chemical Modification of Histidine-Containing Bioactive Peptide Sequences","authors":"Sourav Chatterjee, Bishwajit Paul, Govindaswamy Shanker","doi":"10.1055/s-0043-1775364","DOIUrl":"https://doi.org/10.1055/s-0043-1775364","url":null,"abstract":"<p>The modification of biomolecules, particularly peptides, has garnered considerable attention from researchers, effectively serving as a connection between chemistry and biology. The modification of peptides can facilitate, among others, the generation of peptide drugs, antibody–drug conjugates, and probes for molecular imaging. Herein, we have carefully curated reactions and chemical transformations of bioactive peptide sequences equipped with histidine amino acids that are conducive for biological applications. This Account also highlights strategies for the chemical modification of histidine that might capture the imagination of both peptide researchers and synthetic chemists.</p> <p>1 Introduction</p> <p>2 Histidine Modification in Bioactive Peptides and Proteins</p> <p>3 Remote Bioactive Peptides and Protein Modification Adjacent to Histidine</p> <p>4 Conclusions and Future Directions</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"120 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141253383","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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