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Ruthenium-catalyzed Heck coupling of 3-arylidene-oxindoles with alkenes: a facile synthesis of 3-allylidene-2(3H)-oxindoles. 钌催化的 3-芳基亚烯-氧化吲哚与烯烃的 Heck 偶联：3-芳基亚烯-2(3H)-氧化吲哚的简便合成。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-29 DOI: 10.1039/d4ob01072h
Mohan Prabhakaran, Ramesh Sanjana, Kanniyappan Parthasarathy
{"title":"Ruthenium-catalyzed Heck coupling of 3-arylidene-oxindoles with alkenes: a facile synthesis of 3-allylidene-2(3<i>H</i>)-oxindoles.","authors":"Mohan Prabhakaran, Ramesh Sanjana, Kanniyappan Parthasarathy","doi":"10.1039/d4ob01072h","DOIUrl":"10.1039/d4ob01072h","url":null,"abstract":"<p><p>A simple and efficient Ru(II)-catalyzed olefination of 3-(arylbenzylidene)indolin-2-ones with alkenes is described. This is an atom and step-economical strategy with a wide substrate scope, good functional group tolerance, and suitability for gram scale synthesis. A plausible mechanism is also proposed for this synthetic transformation involving the formation of a 5-membered ruthenacycle and insertion of the alkene followed by β-hydride elimination to deliver the desired product.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142520387","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
Construction of fused heterocycles by visible-light induced dearomatization of nonactivated arenes. 通过可见光诱导非活化烷脱芳构建融合杂环。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-29 DOI: 10.1039/d4ob01530d
Tianyu Liu, Yong Luo, Yidong Liu
{"title":"Construction of fused heterocycles by visible-light induced dearomatization of nonactivated arenes.","authors":"Tianyu Liu, Yong Luo, Yidong Liu","doi":"10.1039/d4ob01530d","DOIUrl":"https://doi.org/10.1039/d4ob01530d","url":null,"abstract":"<p><p>A diverse array of fused [6-6-5] tricyclic heterocycles has been synthesized <i>via</i> the dimerization and dearomative cyclization of benzene derivatives under visible light irradiation. The initiation of the cascade process is likely from aryloxy radicals, engendered through proton-coupled electron transfer by the photoexcited vinylidene <i>ortho</i>-quinone methide (VQM) and a Brønsted base.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142520383","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
Visible-light photoredox-catalyzed three-component radical alkyl-acylation of [1.1.1]propellane. 可见光光氧化催化的 [1.1.1]propellane 三组分自由基烷基酰化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-28 DOI: 10.1039/d4ob01549e
Lanqin Liu, Shengkun Guo, Chengjun Chen, Xiaoyu Shen, Xiaoyun Chen, Huaguang Yu, Ying Han, Qiu Sun, Shaoqun Zhu, Hong Hou
{"title":"Visible-light photoredox-catalyzed three-component radical alkyl-acylation of [1.1.1]propellane.","authors":"Lanqin Liu, Shengkun Guo, Chengjun Chen, Xiaoyu Shen, Xiaoyun Chen, Huaguang Yu, Ying Han, Qiu Sun, Shaoqun Zhu, Hong Hou","doi":"10.1039/d4ob01549e","DOIUrl":"https://doi.org/10.1039/d4ob01549e","url":null,"abstract":"<p><p>We described herein a three-component radical alkyl-acylation of [1.1.1]propellane <i>via</i> a visible-light photoredox single electron transfer process, demonstrating an efficient approach for accessing a diverse array of 1,3-disubstituted BCP ketone derivatives. The synthetic utility of the present radical protocol was further demonstrated by the Baeyer-Villiger oxidation of the BCP ketone for BCP ester formation.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142520389","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
Tetraarylammonium salts – synthesis, properties and emerging use 四芳基铵盐--合成、特性和新兴用途。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-28 DOI: 10.1039/D4OB01386G
Alexander Marriott and Götz Bucher
{"title":"Tetraarylammonium salts – synthesis, properties and emerging use","authors":"Alexander Marriott and Götz Bucher","doi":"10.1039/D4OB01386G","DOIUrl":"10.1039/D4OB01386G","url":null,"abstract":"<p >The chemistry of tetraarylammonium salts, first explored in the 1960s Soviet Union, has long been a dormant field of research. This is owing to the inherent difficulty in adding a fourth benzene ring to the nitrogen atom of the sterically demanding and low-nucleophilicity triphenylamine molecule. Only recently have new developments in synthetic methodology made access to tetraarylammonium salts less of a <em>tour de force</em>, and first applications are beginning to emerge. As a consequence, the number of publications in this field of research is growing. The review covers the complete field of research, from the beginnings to the present day.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 46","pages":" 9021-9031"},"PeriodicalIF":2.9,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/ob/d4ob01386g?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142491289","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
Recent advances in the enantioselective synthesis of chiral sulfones via asymmetric hydrogenation. 通过不对称加氢法对映体选择性合成手性砜的最新进展。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-28 DOI: 10.1039/d4ob01515k
Xiaoxue Wu, Guohua Hou
{"title":"Recent advances in the enantioselective synthesis of chiral sulfones <i>via</i> asymmetric hydrogenation.","authors":"Xiaoxue Wu, Guohua Hou","doi":"10.1039/d4ob01515k","DOIUrl":"https://doi.org/10.1039/d4ob01515k","url":null,"abstract":"<p><p>Chiral sulfones are key structural motifs that extensively exist in natural products, drugs, and biologically active compounds. During the past few decades, rapid development has been made with respect to the highly enantioselective synthesis of chiral sulfones, in which the catalytic asymmetric hydrogenation of unsaturated sulfones provides an efficient and powerful methodology to construct chiral sulfones and their derivatives. This review highlights the progress achieved in transition metal (ruthenium, rhodium, iridium, and nickel) catalyzed direct asymmetric hydrogenation of a variety of unsaturated sulfones from the aspects of the substrate scope, catalytic mechanisms, and applications in the synthesis of biologically active molecules.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142520386","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
A mitochondria-targeted colorimetric and NIR ratiometric fluorescent probe for biothiols with large Stokes shift based on thiol–chromene click reaction† 一种基于硫醇-色素点击反应的线粒体靶向比色和近红外比色荧光探针，用于检测具有较大斯托克斯位移的生物硫醇。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-25 DOI: 10.1039/D4OB01324G
Dongjian Zhu, Aishan Ren and Lin Xue
{"title":"A mitochondria-targeted colorimetric and NIR ratiometric fluorescent probe for biothiols with large Stokes shift based on thiol–chromene click reaction†","authors":"Dongjian Zhu, Aishan Ren and Lin Xue","doi":"10.1039/D4OB01324G","DOIUrl":"10.1039/D4OB01324G","url":null,"abstract":"<p >In this study, a carbazole-based mitochondria-targeted colorimetric and NIR ratiometric fluorescent probe <strong>1</strong> for biothiols based on the thiol–chromene click reaction was subtly designed and synthesized. Upon interaction with biothiols (Cys, Hcy and GSH), the absorption of <strong>1</strong> shifted from 496 nm to 388 nm, while its fluorescence spectrum shifted from 650 nm to 530 nm. These transformations were accompanied by a visible color change from pink to colorless under visible light and from red to green when observed under a 365 nm UV lamp, which can be attributed to the click reaction of biothiols with the α,β-unsaturated ketone of the chromene moiety, subsequent pyran ring-opening and phenol formation as well as 1,6-elimination of a <em>p</em>-hydroxybenzyl moiety yielding <strong>2</strong>. These advancements in <strong>1</strong> have allowed us to ratiometrically detect biothiols with high sensitivity (LODs of 97 nM, 94 nM and 93 nM for Cys, GSH and Hcy, respectively), a large Stokes shift (154 nm) and excellent selectivity. In addition, <strong>1</strong> can target mitochondria and image the fluctuation of intracellular biothiols through fluorescence ratiometry. Furthermore, the novel design strategy of modifying chromene to the N atom of quinoline was proposed for the first time.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 46","pages":" 9113-9120"},"PeriodicalIF":2.9,"publicationDate":"2024-10-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142491283","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
Palladium-catalyzed C-H bond activation and decarboxylation for the assembly of indolo[1,2-f]phenanthridine. 钯催化 C-H 键活化和脱羧以组装吲哚并[1,2-f]菲啶。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-24 DOI: 10.1039/d4ob01383b
Xiaobing Liu, Yong-Liang Ban, Yanjie Liu, Mengdie Zhuang, Yao Zhou
{"title":"Palladium-catalyzed C-H bond activation and decarboxylation for the assembly of indolo[1,2-<i>f</i>]phenanthridine.","authors":"Xiaobing Liu, Yong-Liang Ban, Yanjie Liu, Mengdie Zhuang, Yao Zhou","doi":"10.1039/d4ob01383b","DOIUrl":"https://doi.org/10.1039/d4ob01383b","url":null,"abstract":"<p><p>A direct and convenient strategy for the assembly of indolo[1,2-<i>f</i>]phenanthridine <i>via</i> a Pd-catalyzed tandem cyclization reaction is presented. The current strategy delivers a range of indolo[1,2-<i>f</i>]phenanthridine derivatives by utilizing readily available 1-(2-iodophenyl)-1<i>H</i>-indole and commercially available <i>o</i>-bromobenzoic acids as the starting materials. The reaction features the formation of two C-C bonds through Pd-catalyzed C-H bond activation and decarboxylation.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142491285","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
Zn2+ ions improve the fidelity of metal-mediated primer extension while suppressing intrinsic and Mn2+-induced mutagenic effects by DNA polymerases† Zn2+ 离子提高了金属介导的引物延伸的保真度，同时抑制了 DNA 聚合酶的内在诱变效应和 Mn2+ 诱导的诱变效应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-24 DOI: 10.1039/D4OB01433B
Tatsuya Funai, Natsumi Tanaka, Riyo Sugimachi, Shun-ichi Wada and Hidehito Urata
{"title":"Zn2+ ions improve the fidelity of metal-mediated primer extension while suppressing intrinsic and Mn2+-induced mutagenic effects by DNA polymerases†","authors":"Tatsuya Funai, Natsumi Tanaka, Riyo Sugimachi, Shun-ichi Wada and Hidehito Urata","doi":"10.1039/D4OB01433B","DOIUrl":"10.1039/D4OB01433B","url":null,"abstract":"<p >While Mn<small><sup>2+</sup></small> ions are well-established for reducing the fidelity of DNA polymerases, leading to the misincorporation of nucleotides, our investigation of the effects of metal ions revealed a contrasting role of Zn<small><sup>2+</sup></small>. Here, we demonstrate that Zn<small><sup>2+</sup></small> ions enhance the fidelity of DNA polymerases (the 3′ → 5′ exonuclease-deficient Klenow fragment and Taq DNA polymerase) by suppressing misincorporation during primer extension reactions. Remarkably, Zn<small><sup>2+</sup></small> ions inhibit both intrinsic misincorporation and Mn<small><sup>2+</sup></small>-induced misincorporation of nucleotides. Furthermore, Zn<small><sup>2+</sup></small> ions also effectively suppressed misincorporation during metal-mediated primer extension reactions, which involved forming Ag<small><sup>+</sup></small> and Hg<small><sup>2+</sup></small> ion-mediated base pairs. These findings suggest that Zn<small><sup>2+</sup></small> ions inhibit both intrinsic and Mn<small><sup>2+</sup></small>-induced mismatched base pair formation. Consequently, the combined use of Mn<small><sup>2+</sup></small> and Zn<small><sup>2+</sup></small> ions may offer a strategy for precisely regulating the fidelity of DNA polymerases. Remarkably, Zn<small><sup>2+</sup></small> ions even suppress misincorporation in primer extension reactions that rely on metal-mediated base pairs, and conversely, this suggests that DNA polymerases recognize metal-mediated base pairs such as T-Hg<small><sup>2+</sup></small>-T, C-Ag<small><sup>+</sup></small>-A, and C-Ag<small><sup>+</sup></small>-T as relatively stable base pairs. These results imply that Zn<small><sup>2+</sup></small> ions may also enhance the fidelity of DNA polymerases when incorporating non-canonical nucleobases, potentially paving the way for the expansion of the genetic alphabet.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 46","pages":" 9094-9100"},"PeriodicalIF":2.9,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142491291","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
cisPro stabilization in prolyl carbamates influenced by tetrel bonding interactions† 受四键相互作用的影响，脯氨酰氨基甲酸酯中的顺式PR稳定。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-23 DOI: 10.1039/D4OB01539H
Shreya Banerjee, Shama Tumminakatti, Sudip Ghosh, Vamsee K. Voora and Erode N. Prabhakaran
{"title":"cisPro stabilization in prolyl carbamates influenced by tetrel bonding interactions†","authors":"Shreya Banerjee, Shama Tumminakatti, Sudip Ghosh, Vamsee K. Voora and Erode N. Prabhakaran","doi":"10.1039/D4OB01539H","DOIUrl":"10.1039/D4OB01539H","url":null,"abstract":"<p >NMR spectral and theoretical analyses of homologous prolyl carbamates reveal subtle charge transfer tetrel bonding interactions (TBIs), selectively stabilizing their <em>cis</em>Pro rotamers. These TBIs involve C-terminal-amide to N-terminal carbamate carbonyl–carbonyl (n → π* type) followed by intra-carbamate (n → σ* type) charge transfer interactions exclusively in the <em>cis</em>Pro motif. The number of TBIs and hence the <em>cis</em>Pro stability increase with increasing number of C<small><sup>β</sup></small> groups at the carbamate alcohol. Increasing solvent polarities also increase the relative <em>cis</em>Pro carbamate stabilities.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 46","pages":" 9125-9134"},"PeriodicalIF":2.9,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142491282","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
Radical alkylation of acrylamides with peroxides to access mono/dialkylated fused N-heterocycles. 用过氧化物对丙烯酰胺进行自由基烷基化，以获得单/二烷基化的融合 N-杂环。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-23 DOI: 10.1039/d4ob01555j
Jie Fan, Qinqin Yan, Xueli Wang, Lijun Li, Zejiang Li
{"title":"Radical alkylation of acrylamides with peroxides to access mono/dialkylated fused N-heterocycles.","authors":"Jie Fan, Qinqin Yan, Xueli Wang, Lijun Li, Zejiang Li","doi":"10.1039/d4ob01555j","DOIUrl":"https://doi.org/10.1039/d4ob01555j","url":null,"abstract":"<p><p>A simple mono/dialkylation of acrylamide derivatives was achieved, affording diverse mono/dialkylated benzo[4,5]imidazo[2,1-<i>a</i>]isoquinolines or polycyclic coumarins with good substrate scope. This system used common peroxides as alkylating reagents. Meanwhile, a series of scaled-up reactions and mechanistic explorations well demonstrated the application and reaction process of this cascade system.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142491286","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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