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Photochemically Induced Approaches to the Syntheses of β‐Lactams 光化学诱导的 β-内酰胺合成方法
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-08 DOI: 10.1002/adsc.202400715
Vijay Das, Imtiaz Ahmed, Nikita Gupta, Ajit Gupta
{"title":"Photochemically Induced Approaches to the Syntheses of β‐Lactams","authors":"Vijay Das, Imtiaz Ahmed, Nikita Gupta, Ajit Gupta","doi":"10.1002/adsc.202400715","DOIUrl":"https://doi.org/10.1002/adsc.202400715","url":null,"abstract":"The synthesis of β‐lactam scaffolds is of paramount importance due to their extensive applications in pharmaceuticals, particularly as antibiotics. Visible light photocatalysis has emerged as a revolutionary approach in this domain, providing a sustainable and efficient pathway for β‐lactam construction. In this review, we meticulously discuss the recent developments in the synthesis of photocatalysed β‐lactam frameworks.A key focus is the Staudinger reaction, traditionally a cornerstone in β‐lactam synthesis, and its adaptation to visible light photocatalysis. We explore the mechanistic intricacies of the Staudinger reaction under photochemical conditions, along with other pivotal cyclization strategies enabled by visible light. By illuminating the novel photocatalytic routes to β‐lactams, this review provides a thorough understanding of the state‐of‐the‐art techniques and sets the stage for future innovations in the green synthesis of these critical compounds.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"206 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142384390","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
On the Functionalization of C60 with Vinylallenes Generated in situ by Rhodium Catalysis 铑催化原位生成的乙烯基烯烃对 C60 的官能化作用
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-06 DOI: 10.1002/adsc.202401163
Cristina Castanyer, Albert Artigas, Miquel Solà, Anna Pla-Quintana, Anna Roglans
{"title":"On the Functionalization of C60 with Vinylallenes Generated in situ by Rhodium Catalysis","authors":"Cristina Castanyer, Albert Artigas, Miquel Solà, Anna Pla-Quintana, Anna Roglans","doi":"10.1002/adsc.202401163","DOIUrl":"https://doi.org/10.1002/adsc.202401163","url":null,"abstract":"The functionalization of fullerenes is important for several reasons, primarily related to enhancing their chemical reactivity, solubility, and potential of applications in optoelectronics and biomedicine. In this study, we present a novel approach to functionalize C60 through a cascade process encompassing an unprecedented Rh-catalyzed cycloisomerization of 1,6-allenynes to in situ generate a vinylallene that is followed by a Diels-Alder reaction with pristine fullerene, resulting in the formation of 6,6-fused bicyclic fullerene derivatives. The mechanism governing this process was elucidated by DFT calculations and confirmed by deuterium labelling and control experiments, demonstrating the critical role of traces of water in the reaction medium to mediate the observed reactivity.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"7 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142379362","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-Mediated Cascade Reaction of CF3-Imidoyl Sulfoxonium Ylides and Diimides for the Synthesis of Functionalized Amidines 以碱为介质的 CF3-酰亚胺基磺氧化鎓酰化物和二亚胺的级联反应合成功能化脒类化合物
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-06 DOI: 10.1002/adsc.202400996
Sihao Ling, Qihua Chen, Zhengkai Chen
{"title":"Base-Mediated Cascade Reaction of CF3-Imidoyl Sulfoxonium Ylides and Diimides for the Synthesis of Functionalized Amidines","authors":"Sihao Ling, Qihua Chen, Zhengkai Chen","doi":"10.1002/adsc.202400996","DOIUrl":"https://doi.org/10.1002/adsc.202400996","url":null,"abstract":"A base-mediated cascade reaction of CF3-imidoyl sulfoxonium ylides (TFISYs) and diimides has been developed for the preparation of functionalized amidines. In the transformation, a cascade nucleophilic addition and subsequent [2,3]-sigmatropic rearrangement of sulfoxonium ylide occur to enable an intramolecular migration of dimethyl sulfoxide (DMSO). The unexpected result of the developed protocol demonstrates the chameleonic reactivity of TFISYs.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"224 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142383838","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
NHC-Catalyzed Synthesis of 2-Aroylchromones and Their Application in the Synthesis of Wrightiadione Analogues NHC 催化合成 2-Aroylchromones 及其在合成赖皮二酮类似物中的应用
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-04 DOI: 10.1002/adsc.202400955
Futa Koyama, Justin Lamb, Moena Hirao, Noriyuki Suzuki, Masahiro Yoshizawa-Fujita, Toyonobu Usuki, Yumiko Suzuki
{"title":"NHC-Catalyzed Synthesis of 2-Aroylchromones and Their Application in the Synthesis of Wrightiadione Analogues","authors":"Futa Koyama, Justin Lamb, Moena Hirao, Noriyuki Suzuki, Masahiro Yoshizawa-Fujita, Toyonobu Usuki, Yumiko Suzuki","doi":"10.1002/adsc.202400955","DOIUrl":"https://doi.org/10.1002/adsc.202400955","url":null,"abstract":"With a number of biologically active members, 2-aroylchromones are valuable synthetic targets. A direct route towards 2-aroylchromones from 2-(methylsulfonyl)chromones and aldehydes via NHC-catalyzed C-C bond formation was developed. Yields of the synthesized 2-aroylchromones were up to 85%. Chromones with angioprotective or antibacterial properties were easily synthesized using the method developed. Additionally, the synthetic utility of the afforded chromones was demonstrated by using them to synthesize the anticancer compound wrightiadione and analogues of it.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"223 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142374548","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
One-pot Synthesis of Sulfonylated 5-Aroyl-2-arylpyridines via Ruthenium-Catalyzed and K2S2O8-Mediated Domino Annulation of β-Ketosulfones with DMF 通过钌催化和 K2S2O8 介导的 β-酮砜与 DMF 的多米诺环化反应，一步法合成磺酰化 5-丙酰基-2-芳基吡啶
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-04 DOI: 10.1002/adsc.202401116
Meng-Yang Chang, Chi-Ru Yang, Yeh-Long Chen
{"title":"One-pot Synthesis of Sulfonylated 5-Aroyl-2-arylpyridines via Ruthenium-Catalyzed and K2S2O8-Mediated Domino Annulation of β-Ketosulfones with DMF","authors":"Meng-Yang Chang, Chi-Ru Yang, Yeh-Long Chen","doi":"10.1002/adsc.202401116","DOIUrl":"https://doi.org/10.1002/adsc.202401116","url":null,"abstract":"Ruthenium-catalyzed and K2S2O8-mediated synthesis of diverse sulfonylated 5-aroyl-2-arylpyridines was developed through one-pot stepwise annulation of two molecules of β-ketosulfones and N,N-dimethylformamide (DMF) under the sealed tube conditions. In the overall process, DMF acts as the synthon of one carbon and one imino moiety in the construction of pyridine skeleton via cascade formation of single (C-C/C-N) and double (C=C/C=N) bonds under refluxing DMF conditions. Plausible reaction mechanism is proposed and discussed.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"13 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142374547","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
Pyridine‐Boryl Radical‐Catalyzed [3 + 2] Cycloadditions of Alkyne‐Tethered Cyclopropyl Ketones 吡啶-硼基自由基催化的炔拴环丙基酮 [3 + 2] 环加成反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-04 DOI: 10.1002/adsc.202401015
Hua Huang, Xiao-Die An, Yi-Fan Wang, Yun-Xuan Tan, Ping Tian
{"title":"Pyridine‐Boryl Radical‐Catalyzed [3 + 2] Cycloadditions of Alkyne‐Tethered Cyclopropyl Ketones","authors":"Hua Huang, Xiao-Die An, Yi-Fan Wang, Yun-Xuan Tan, Ping Tian","doi":"10.1002/adsc.202401015","DOIUrl":"https://doi.org/10.1002/adsc.202401015","url":null,"abstract":"Bicyclo[3.3.0]octanes represent crucial structural motifs found in various bioactive natural compounds. In this study, we present the first metal‐free formal [3 + 2] cycloadditions of alkyne‐tethered cyclopropyl ketones via pyridine‐boryl radical catalysis, affording bicyclo[3.3.0]octanes with high efficiency and broad substrate scope. This reaction features the generation of ketyl radical by pyridine‐boryl radical and a consecutive 5‐exo‐dig and 5‐exo‐trig radical cascade process.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"63 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142374249","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
Catalyst-Controlled Regiodivergent C–H Alkynylation of 2-Pyridylthiophenes 催化剂控制的 2-吡啶基噻吩的 C-H 炔基化反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-04 DOI: 10.1002/adsc.202400856
Yuting Gui, Yaokun Zhao, Xingchi Li, Taoyuan Liang, Shuangliang Zhao, Zhuan Zhang
{"title":"Catalyst-Controlled Regiodivergent C–H Alkynylation of 2-Pyridylthiophenes","authors":"Yuting Gui, Yaokun Zhao, Xingchi Li, Taoyuan Liang, Shuangliang Zhao, Zhuan Zhang","doi":"10.1002/adsc.202400856","DOIUrl":"https://doi.org/10.1002/adsc.202400856","url":null,"abstract":"Different catalysts are presented to overcome or augment a substrate’s innate regioselectivity. Rhodium was found to overcome the innate C3-selectivity <i>via</i> chelation-assisted rhodation. Conversely, palladium was found to enhance the innate C5-selectivity <i>via </i>electrophilic palladation. These reactions allow for the formation of a diverse range of synthetically versatile C3- and C5-alkynylated products from 2-pyridylthiophenes. Notably, this strategy was successfully employed in the straightforward synthesis of π-extended functionalized 2-pyridylthiophenes, which could be converted into more valuable compounds.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"192 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142374470","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 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 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-04 DOI: 10.1002/adsc.202400456
Delin Tang, Fang Zhang, Jinyun Luo, Zhihua Cai, Lin He, Guang-Fen Du
{"title":"Synthesis of Vinyl Sulfones and Benzoxathiins via Base-Catalyzed Reactions of o-Hydroxyaryl Thiosulfonates and Ynones","authors":"Delin Tang, Fang Zhang, Jinyun Luo, Zhihua Cai, Lin He, Guang-Fen Du","doi":"10.1002/adsc.202400456","DOIUrl":"https://doi.org/10.1002/adsc.202400456","url":null,"abstract":"The cyclization reaction and hydrosulfonylation reaction of ynones have been simultaneously realized through a single operation. Under the mediation of cesium carbonate, different S-(α-hydroxyaryl) aryl thiosulfonates reacted with various ynones to produce functionalized vinyl sulfones in 37%-83% yields with E-selectivity. At the same time, a variety of benzoxathiins were formed in 42%-97% yields.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"51 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-04","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
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 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-04 DOI: 10.1002/adsc.202401007
Ravikumar Ladumor, Sourav Samanta, Sermadurai Selvakumar
{"title":"Photocatalytic Silylation of Aryl Alkynoates: Synthesis of Silylated Coumarins","authors":"Ravikumar Ladumor, Sourav Samanta, Sermadurai Selvakumar","doi":"10.1002/adsc.202401007","DOIUrl":"https://doi.org/10.1002/adsc.202401007","url":null,"abstract":"Herein, we reported the photocatalytic synthesis of 3‐silyl coumarins using hydrosilanes as the silyl radical source with aryl alkynoates. Readily prepared N‐aminopyridinium salts act as hydrogen atom transfer reagents for generating silyl radicals under photoredox catalysis. The reaction proceeds through silyl radical addition to alkyne followed by radical cascade cyclization/migration with subsequent oxidation and aromatization to give desired 3‐silyl coumarins in 34% to 89% yield.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"23 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-04","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
Visible-Light Photoredox-Catalyzed Trifunctionalization of Unactivated Alkenes via Diamidation and Cyano Migration 通过二胺化和氰迁移实现可见光光氧化催化未活化烯烃的三官能化
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-04 DOI: 10.1002/adsc.202400987
Abuthayir Mohamathu Ghouse, Bathula Maheswari, Srirama Murthy Akondi
{"title":"Visible-Light Photoredox-Catalyzed Trifunctionalization of Unactivated Alkenes via Diamidation and Cyano Migration","authors":"Abuthayir Mohamathu Ghouse, Bathula Maheswari, Srirama Murthy Akondi","doi":"10.1002/adsc.202400987","DOIUrl":"https://doi.org/10.1002/adsc.202400987","url":null,"abstract":"A visible-light-promoted, nitrogen-centered radical-initiated trifunctionalization of 5-hexenenitriles via diamidation and 1,4-cyano migration, using 1 mol% fac-Ir(ppy)₃ as the photoredox catalyst, is reported. In this protocol, the O-acylhydroxylamine derivative acts as a bifunctional reagent, and the carbonitrile solvent also participates in the reaction. This transformation proceeds at room temperature without the need for an external oxidant or reductant, yielding a wide range of functionalized β-amino nitriles, including the derivatives of natural products and pharmaceuticals.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"1 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142374450","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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