Organic & Biomolecular Chemistry最新文献

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Gold-catalyzed fluorination of alkynes/allenes: mechanistic explanations and reaction scope. 金催化的炔/烯氟化反应:机理解释和反应范围。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-08 DOI: 10.1039/d4ob01579g
Deblina Singha Roy, Yogesh Bhaskar Singh Tanwer, Snigdha Rani Patra, Shivam Kumar, Sabyasachi Bhunia, Debjit Das
{"title":"Gold-catalyzed fluorination of alkynes/allenes: mechanistic explanations and reaction scope.","authors":"Deblina Singha Roy, Yogesh Bhaskar Singh Tanwer, Snigdha Rani Patra, Shivam Kumar, Sabyasachi Bhunia, Debjit Das","doi":"10.1039/d4ob01579g","DOIUrl":"10.1039/d4ob01579g","url":null,"abstract":"<p><p>Since the beginning of this century, there has been a great deal of research on homogeneous gold-catalyzed alkyne fluorination due to the precious values of fluorinated scaffolds in many bioactive natural products, drugs, and agrochemicals. This area of research, which originally took advantage of gold's mild Lewis acidity and tendency to form π-complexes with alkynes, has gained new momentum after Sadighi's discovery in 2007 of Au-catalyzed hydrofluorination of internal alkynes. The methods have enabled direct access to valuable fluoroalkanes, fluoroalkenes, α-fluorocarbonyls, and fluorinated carbo- and hetero-cycles in one pot from readily available alkyne precursors. Both nucleophilic and electrophilic fluorination modes with versatile reactivity have been used to achieve several new cascade reactions. This study covers the literature reports published since 2007 and provides a comprehensive summary of the methods, applications, and mechanistic insights into gold-catalyzed alkyne fluorination using electrophilic and nucleophilic fluorinating reagents.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142602439","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Facile synthesis of functionalized quinolinones in a green reaction medium and their photophysical properties. 在绿色反应介质中轻松合成功能化喹啉酮及其光物理特性。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-07 DOI: 10.1039/d4ob01390e
Pari Keerthana, Sundararajan Suresh, Fazlur Rahman Nawaz Khan
{"title":"Facile synthesis of functionalized quinolinones in a green reaction medium and their photophysical properties.","authors":"Pari Keerthana, Sundararajan Suresh, Fazlur Rahman Nawaz Khan","doi":"10.1039/d4ob01390e","DOIUrl":"10.1039/d4ob01390e","url":null,"abstract":"<p><p>A facile and green chemical approach was successfully developed to construct functionalized quinolinones utilizing substituted alcohols, alkyl acetoacetate, and α-bromo ketones. Various quinolinones bearing either electron-rich or electron-deficient groups at different positions were synthesized in moderate to good yields under mild reaction conditions. The plausible mechanistic pathway for this transformation is supported by experimental evidence and control experiments. This simple approach for synthesizing quinolinones could open new avenues for discovering novel biological and pharmaceutical compounds. The use of affordable nickel catalysts, mild reaction conditions, operational simplicity, and high atom economy are attractive features of this method. Furthermore, the synthetic efficiency has been demonstrated through gram-scale experiments. Our research also provides valuable insights into the photophysical properties of the synthesized derivatives. Notably, compound 6n exhibited the highest Stokes shift (216 nm) in DCM solvent. Furthermore, compounds 5d and 6j showed positive solvatochromism, displaying a stronger emission as the solvent polarity increased. Additionally, compound 6j displayed aggregation-induced emission (AIE) properties in a DMSO : water mixture, making it suitable for use as a security ink, highlighting its potential applications in various fields.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142602437","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Size and shape matter for micellar catalysis using light-responsive azobenzene surfactants. 使用光响应偶氮苯表面活性剂进行胶束催化时的尺寸和形状问题。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-07 DOI: 10.1039/d4ob01587h
Camille Blayo, Beatrice E Jones, Michael J Bennison, Rachel C Evans
{"title":"Size and shape matter for micellar catalysis using light-responsive azobenzene surfactants.","authors":"Camille Blayo, Beatrice E Jones, Michael J Bennison, Rachel C Evans","doi":"10.1039/d4ob01587h","DOIUrl":"10.1039/d4ob01587h","url":null,"abstract":"<p><p>The micellar catalysis of a model Claisen-Schmidt aldol condensation reaction using heterogeneous nanoreactors based on cationic azobenzene trimethylammonium bromide (AzoTAB) photosurfactants is investigated. Under UV irradiation, AzoTABs undergo a <i>trans</i>-<i>cis</i> photoisomerisation, which changes not only the critical micelle concentration, but also the shape and size of the micelle. The effect of surfactant structure (tail and spacer lengths), concentration and temperature on the reaction yield were investigated. Monitoring of the zeta potential during the reaction indicated that it proceeds at the micelle/water interface for AzoTABs, with the enolate intermediate stabilised in micelle/water interface (<i>i.e.</i> the Stern layer). The reaction yield was found to correlate directly to micellar shape and size, with smaller, more spherical micelles typical of <i>cis</i>-AzoTABs favouring higher reaction efficiencies.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11563304/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142602445","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Paired electrocatalysis enabled oxidative coupling of styrenes with alkyl radicals. 成对电催化使苯乙烯与烷基自由基发生氧化偶联。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-07 DOI: 10.1039/d4ob01605j
Dong Li, Ling Zhang, Daixi Li, Peng Yu, Tao Shen
{"title":"Paired electrocatalysis enabled oxidative coupling of styrenes with alkyl radicals.","authors":"Dong Li, Ling Zhang, Daixi Li, Peng Yu, Tao Shen","doi":"10.1039/d4ob01605j","DOIUrl":"10.1039/d4ob01605j","url":null,"abstract":"<p><p>A paired electrocatalysis strategy for intermolecular oxidative cross-dehydrocoupling between styrenes and ethers or <i>p</i>-methylphenol derivatives using ketone as a mild oxidant is described. This approach enables the generation of Csp<sup>3</sup> carbon-centered radicals through anodic oxidation, followed by reductive coupling of ketones at the cathode, ultimately yielding valuable oxidative alkylation products.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142589638","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Interrogating the potential of helical aromatic foldamers for protein recognition. 探究螺旋芳香折叠器识别蛋白质的潜力。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-06 DOI: 10.1039/d4ob01436g
Sunbum Kwon, Vasily Morozov, Lingfei Wang, Pradeep K Mandal, Stéphane Chaignepain, Céline Douat, Ivan Huc
{"title":"Interrogating the potential of helical aromatic foldamers for protein recognition.","authors":"Sunbum Kwon, Vasily Morozov, Lingfei Wang, Pradeep K Mandal, Stéphane Chaignepain, Céline Douat, Ivan Huc","doi":"10.1039/d4ob01436g","DOIUrl":"https://doi.org/10.1039/d4ob01436g","url":null,"abstract":"<p><p>A biotinylated helical aromatic oligoamide foldamer equivalent in size to a 24mer peptide was designed without any prejudice other than to display various polar and hydrophobic side chains at its surface. It was synthesized on solid phase, its <i>P</i>- and <i>M</i>-helical conformers were separated by HPLC on a chiral stationary phase, and the solid state structure of a non-biotinylated analogue was elucidated by X-ray crystallography. Pull-down experiments from a yeast cell lysate using the foldamer as a bait followed by proteomic analysis revealed potential protein binding partners. Three of these proteins were recombinantly expressed. Biolayer interferometry showed submicromolar binding demonstrating the potential of a given foldamer to have affinity for certain proteins in the absence of design considerations. Yet, binding selectivity was low in all three cases since both <i>P</i>- and <i>M</i>-conformers bound to the proteins with similar affinities.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142581304","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 the 5/5-spiroindimicin alkaloids: development of a general synthetic approach and biological investigations. 5/5 螺吲哚生物碱的合成:通用合成方法的开发和生物学研究。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-06 DOI: 10.1039/d4ob01552e
Ankush Banerjee, Tiffany A Brisco, Sneha Ray, Arani Datta, Xiaoyu Zhang, Zhen Zhang, Alexander A Busse, Hanspeter Niederstrasser, Krissty Sumida, Bruce A Posner, Dawn M Wetzel, Margaret A Phillips, Myles W Smith
{"title":"Synthesis of the 5/5-spiroindimicin alkaloids: development of a general synthetic approach and biological investigations.","authors":"Ankush Banerjee, Tiffany A Brisco, Sneha Ray, Arani Datta, Xiaoyu Zhang, Zhen Zhang, Alexander A Busse, Hanspeter Niederstrasser, Krissty Sumida, Bruce A Posner, Dawn M Wetzel, Margaret A Phillips, Myles W Smith","doi":"10.1039/d4ob01552e","DOIUrl":"https://doi.org/10.1039/d4ob01552e","url":null,"abstract":"<p><p>We describe the development of a unified synthetic strategy for the preparation of all known 5/5-spirocyclic spiroindimicin (SPM) alkaloids, namely spiroindimicins B-G. The present synthetic route relies on four fundamental transformations: Grignard-based fragment coupling between halogenated pyrrolemetal and isatin partners, Suzuki coupling to generate a triaryl scaffold encompassing all requisite skeletal atoms of the natural products, Lewis acid-mediated spirocyclization to construct the 5/5-spirocyclic core, and chemoselective lactam reduction. The developed syntheses are step-economic (6-7 steps from commercial materials), scalable, and amenable to analogue synthesis. Preliminary investigations into a catalytic asymmetric spirocyclization towards an enantioselective SPM synthesis are also described. Further studies of the antiparasitic properties of this class have revealed promising activity against <i>T. brucei</i> for certain congeners. Together with our prior approach to the 6/5-family members, our work constitutes a synthetic solution to all known spiroindimicin natural products.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142581308","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Electrochemical one-pot cascade synthesis of thio(seleno)cyanato-substituted thiazolidine-2-imines without external electrolyte. 无外加电解质电化学一锅级联合成硫(硒)氰基取代的噻唑烷-2-亚胺。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-05 DOI: 10.1039/d4ob01626b
Xiao Yu, Liqiang Hao, Xian Liu, Shengkui Jin, Yangchen Li, Yiping Liu, Yafei Ji
{"title":"Electrochemical one-pot cascade synthesis of thio(seleno)cyanato-substituted thiazolidine-2-imines without external electrolyte.","authors":"Xiao Yu, Liqiang Hao, Xian Liu, Shengkui Jin, Yangchen Li, Yiping Liu, Yafei Ji","doi":"10.1039/d4ob01626b","DOIUrl":"https://doi.org/10.1039/d4ob01626b","url":null,"abstract":"<p><p>A novel synthetic method has been developed for generating thio(seleno)cyanato-substituted thiazolidine-2-imines <i>via</i> an electrochemical one-pot cascade reaction. This reaction employs isothiocyanates, <i>N</i>-2-en-1-amines, and KSCN (or KSeCN) under mild conditions, obviating the need for metals, chemical oxidants, and external electrolytes. The protocol is effective with unactivated alkenes and facilitates the synthesis of five- and six-membered thio(seleno)cyanato-substituted thiazolidine-2-imines. The versatility is demonstrated by its straightforward operation and scalability to gram-scale production, underscoring its potential for broader application.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142575500","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 electron donor-acceptor (EDA) complex promoted arylation of 2-oxo-2H-chromene-3-carbonitriles under visible light irradiation. 新型电子供体-受体(EDA)复合物在可见光照射下促进了 2-oxo-2H-chromene-3-carbonitriles 的芳基化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-05 DOI: 10.1039/d4ob01493f
Tanmoy Sahoo, Dasari Vijaya Prasanna, B Sridhar, B V Subba Reddy
{"title":"Novel electron donor-acceptor (EDA) complex promoted arylation of 2-oxo-2<i>H</i>-chromene-3-carbonitriles under visible light irradiation.","authors":"Tanmoy Sahoo, Dasari Vijaya Prasanna, B Sridhar, B V Subba Reddy","doi":"10.1039/d4ob01493f","DOIUrl":"https://doi.org/10.1039/d4ob01493f","url":null,"abstract":"<p><p>An efficient and operationally simple photochemical method has been demonstrated under transition metal-free, photocatalyst-free, and oxidant-free conditions. In recent times, diaryliodonium salts have become one of the most popular arylating sources under photoinduced conditions. Herein, we developed a visible light induced arylation of heterocycles using an EDA complex that is formed <i>in situ</i> from 2,6-lutidine and diaryliodonium triflate. Under light irradiation, the EDA complex generates the aryl radical that undergoes addition with 2-oxo-2<i>H</i>-chromene-3-carbonitriles <i>via</i> an SET process. This method serves as an effective tool to access biologically active and pharmaceutically relevant coumarin scaffolds.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142575503","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
[Au]/[Ag]-catalysed synthesis of non-hydrolysable C-glycosides. [金]/[银]催化的非水解 C-糖苷的合成。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-04 DOI: 10.1039/d4ob01339e
Saptashwa Chakraborty, Daksh Telang, Bijoyananda Mishra, Srinivas Hotha
{"title":"[Au]/[Ag]-catalysed synthesis of non-hydrolysable <i>C</i>-glycosides.","authors":"Saptashwa Chakraborty, Daksh Telang, Bijoyananda Mishra, Srinivas Hotha","doi":"10.1039/d4ob01339e","DOIUrl":"https://doi.org/10.1039/d4ob01339e","url":null,"abstract":"<p><p>Many <i>C</i>-glycosides are found in natural products, drugs and small molecular probes. Herein, we report the synthesis of <i>C</i>-glycosides by the [Au]/[Ag]-catalysed activation of ethynylcyclohexyl glycosyl carbonate donors. This mild, catalytic, fast and high yielding protocol enables the synthesis of a diverse array of <i>C</i>-glycosides that were otherwise challenging to synthesize.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142566523","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Silver-mediated radical cascade trifluoromethylthiolation/cyclization of benzimidazole derivatives with AgSCF3. 以 AgSCF3 为媒介的苯并咪唑衍生物的银介导自由基级联三氟甲基硫代化/环化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-04 DOI: 10.1039/d4ob01582g
Pan Liu, Yang Geng, Dapeng Zou, Yangjie Wu, Yusheng Wu
{"title":"Silver-mediated radical cascade trifluoromethylthiolation/cyclization of benzimidazole derivatives with AgSCF<sub>3</sub>.","authors":"Pan Liu, Yang Geng, Dapeng Zou, Yangjie Wu, Yusheng Wu","doi":"10.1039/d4ob01582g","DOIUrl":"https://doi.org/10.1039/d4ob01582g","url":null,"abstract":"<p><p>A silver-mediated cascade trifluoromethylthiolation/cyclization of unactivated alkenes has been investigated. This strategy employs AgSCF<sub>3</sub> as the trifluoromethylthiolating reagent to obtain a variety of useful trifluoromethylthiolated tricyclic imidazol derivatives in reasonable yields. Preliminary mechanistic studies indicate that the present reaction takes place <i>via</i> a radical process. This method is distinguished by its atom economy, wide functional group compatibility, operational simplicity and product diversity.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142566564","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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