发布求助
文献互助 智能选刊 最新文献

Organic & Biomolecular Chemistry最新文献

筛选
英文 中文
Assembly of functionalized gem-difluoroalkenes via photocatalytic defluorocyanoalkylation and defluoroacylation of α-CF3 styrenes with oxime esters. 通过光催化α-CF3 苯乙烯与肟酯的脱氟氰基烷基化和脱氟酰基化组装官能化 gem-二氟烯烃。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-29 DOI: 10.1039/d4ob01496k
Chan Ai, Tao Wang, Yu Bao, Shenghu Yan, Yue Zhang, Jia-Yin Wang
{"title":"Assembly of functionalized <i>gem</i>-difluoroalkenes <i>via</i> photocatalytic defluorocyanoalkylation and defluoroacylation of α-CF<sub>3</sub> styrenes with oxime esters.","authors":"Chan Ai, Tao Wang, Yu Bao, Shenghu Yan, Yue Zhang, Jia-Yin Wang","doi":"10.1039/d4ob01496k","DOIUrl":"https://doi.org/10.1039/d4ob01496k","url":null,"abstract":"<p><p>We report an efficient photocatalytic protocol for the defluorocyanoalkylation and defluoroacylation of α-trifluoromethyl styrenes by utilizing oxime esters as radical donors, allowing for the preparation of diverse <i>gem</i>-difluoroalkenes. The treatment of α-trifluoromethyl styrenes with cyclobutanone oxime esters led to the formation of distal cyano group-anchored <i>gem</i>-difluoroalkenes. Notably, adding K<sub>2</sub>CO<sub>3</sub> as an inorganic base to the photocatalytic system afforded γ,γ-difluoroallylic ketones by utilizing acyl oxime esters as the acylating agents. Preliminary mechanistic investigations into this reaction pathway revealed the involvement of single-electron reduction, C-C bond cleavage initiated by iminyl radicals, radical addition, and β-fluoride elimination steps.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142520382","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 chlorine-free microwave-assisted, ionic liquid-catalyzed esterification of arylsulfonic acids with alcohols: an experimental and theoretical study. 无氯微波辅助离子液体催化的芳基磺酸与醇的酯化反应：实验和理论研究。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-29 DOI: 10.1039/d4ob01516a
Bianka Huszár, Zoltán Mucsi, György Keglevich
{"title":"A chlorine-free microwave-assisted, ionic liquid-catalyzed esterification of arylsulfonic acids with alcohols: an experimental and theoretical study.","authors":"Bianka Huszár, Zoltán Mucsi, György Keglevich","doi":"10.1039/d4ob01516a","DOIUrl":"https://doi.org/10.1039/d4ob01516a","url":null,"abstract":"<p><p>In the area of esterification of heteroatomic acids, after the microwave-assisted ionic liquid-catalyzed esterification of phosphinic acids, the esterification of arylsulfonic acids was also developed applying a 14-fold excess of alcohols at 200 °C in the presence of 10% butyl-methylimidazolium hexafluorophosphate as an additive. The esterifications were optimized, and the effect of the substituents in the aromatic ring was evaluated. At the same time, a similar procedure described by Mandal <i>et al.</i> using only one equivalent of alcohol at 120 °C for 5 min in toluene was refuted. The mechanism and energetics of the reaction of benzenesulfonic acid and butyl alcohol were determined at the B3LYPD3/def2TZVP[PCM(BuOH)] level of theory using the explicit-implicit solvent model, and, as a comparison, the implicit solvent model. Three possible reaction pathways were explored: the direct esterification of benzenesulfonic acid through an S<sub>N</sub>2 protocol including the nucleophilic addition of butyl alcohol to the SO function of the sulfonic acid <i>via</i> an intermediate with a hexavalent-pentacoordinated S atom (<b><i>Route I</i></b>), <i>via</i> protonation of the alcohol by the arenesulfonic acid followed by the recombination of the sulfonate anion and the alkyl cation formed by dehydration (<b><i>Route II</i></b>), and an S<sub>N</sub>1 route involving the initial formation of a sulfonium cation by dehydration of the protonated sulfonic acid followed by the nucleophilic attack of the alcohol (<b><i>Route III</i></b>). Judging from the energetics of the three potential pathways, the alkylating esterification (<b><i>Route II</i></b>) seems to be the predominant route. Microwave irradiation may overcome the enthalpy of activation of 132 kJ mol<sup>-1</sup> required for this protocol. The addition-elimination (S<sub>N</sub>2) sequence (<b><i>Route I</i></b>) may also be operative as a minor reaction component.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142520381","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
Synthetic studies towards naturally occurring aporpinones: asymmetric synthesis of 1'-deshydroxymethyl analogues of aporpinone A, aporpinone B and 4'-hydroxyaporpinone A. 天然芹菜酮的合成研究：芹菜酮 A、芹菜酮 B 和 4'-hydroxyaporpinone A 的 1'-deshydroxymethyl 类似物的不对称合成。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-29 DOI: 10.1039/d4ob01517g
Kishor Kumar Mandal, Swagata Das, Samik Nanda
{"title":"Synthetic studies towards naturally occurring aporpinones: asymmetric synthesis of 1'-deshydroxymethyl analogues of aporpinone A, aporpinone B and 4'-hydroxyaporpinone A.","authors":"Kishor Kumar Mandal, Swagata Das, Samik Nanda","doi":"10.1039/d4ob01517g","DOIUrl":"https://doi.org/10.1039/d4ob01517g","url":null,"abstract":"<p><p>Herein, we disclose the asymmetric total synthesis of 1'-deshydroxymethyl analogues of naturally occurring aporpinone A, aporpinone B, and 4'-hydroxyaporpinone A, featuring a γ-<i>Z</i>-alkylidene butenolide framework. Bimetallic (Pd-Cu) cascade cyclization on a properly functionalized bis-alkyne with <i>Z</i>-2-bromoacrylic acid was employed to construct the butenolide framework with an alkyne appendage. Late-stage enzymatic kinetic resolution (EKR) was adopted for the synthesis of (<i>R</i>)-1'-deshydroxymethyl aporpinone A and (<i>S</i>)-1'-deshydroxymethyl acetyl aporpinone A. The enantiopure bis-alkyne required for the synthesis of (<i>S</i>)-1'-deshydroxymethyl aporpinone B and (<i>R</i>)-1'-deshydroxymethyl 4'-hydroxyaporpinone A was constructed through the Sonogashira cross-coupling reaction.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142520388","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
Highly selective synthesis of selenium-containing (E)-N-propenolquinazolinones via FeCl3-mediated cascade reaction of propargyl quinazoline-4-yl ethers with diselenides. 通过 FeCl3 介导的丙炔基喹唑啉-4-基醚与二硒化物的级联反应，高选择性合成含硒的 (E)-N-丙烯醇喹唑啉酮。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-29 DOI: 10.1039/d4ob01498g
Xinqin Zhang, Qin Yang, Xiaofeng Zeng, Yang Fu, Qiuping Ding, Yiyuan Peng
{"title":"Highly selective synthesis of selenium-containing (<i>E</i>)-<i>N</i>-propenolquinazolinones <i>via</i> FeCl<sub>3</sub>-mediated cascade reaction of propargyl quinazoline-4-yl ethers with diselenides.","authors":"Xinqin Zhang, Qin Yang, Xiaofeng Zeng, Yang Fu, Qiuping Ding, Yiyuan Peng","doi":"10.1039/d4ob01498g","DOIUrl":"https://doi.org/10.1039/d4ob01498g","url":null,"abstract":"<p><p>An effective approach for the highly selective synthesis of selenium-containing (<i>E</i>)-<i>N</i>-propenolquinazolinones <i>via</i> an FeCl<sub>3</sub>·6H<sub>2</sub>O mediated cascade reaction of propargyl quinazoline-4-yl ethers and diselenides has been developed. Mechanistic investigations revealed that the reaction of FeCl<sub>3</sub> and (PhSe)<sub>2</sub> generates, <i>in situ</i>, the electrophilic species PhSe[FeCl<sub>4</sub>]·6H<sub>2</sub>O, which triggers the cascade reaction.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142520384","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
Pushing a bistable [2]rotaxane out of equilibrium and isolation of the metastable-state co-conformation. 将双稳态 [2]rotaxane 推离平衡状态并分离出蜕变态共构象。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-29 DOI: 10.1039/d4ob01419g
Mathias S Neumann, Sofie K Jensen, Rikke Frederiksen, Sissel S Andersen, Kasper M Beck, Jan O Jeppesen
{"title":"Pushing a bistable [2]rotaxane out of equilibrium and isolation of the metastable-state co-conformation.","authors":"Mathias S Neumann, Sofie K Jensen, Rikke Frederiksen, Sissel S Andersen, Kasper M Beck, Jan O Jeppesen","doi":"10.1039/d4ob01419g","DOIUrl":"https://doi.org/10.1039/d4ob01419g","url":null,"abstract":"<p><p>Incorporating a steric barrier between the two stations in a bistable [2]rotaxane based on monopyrrolotetrathiafulvalene and cyclobis(paraquat-<i>p</i>-phenylene) allows the high-energy metastable-state co-conformation to be physically isolated following a single redox cycle, thus making it possible to store energy (4.4 J L<sup>-1</sup>) and to follow its interconversion back to the ground-state co-conformation.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142520385","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
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":null,"pages":null},"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":null,"pages":null},"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
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 : 2024-10-28 DOI: 10.1039/d4ob01539h
Shreya Banerjee, Shama Tumminakatti, Sudip Ghosh, Vamsee K Voora, Erode N Prabhakaran
{"title":"<i>cis</i>Pro stabilization in prolyl carbamates influenced by tetrel bonding interactions.","authors":"Shreya Banerjee, Shama Tumminakatti, Sudip Ghosh, Vamsee K Voora, Erode N Prabhakaran","doi":"10.1039/d4ob01539h","DOIUrl":"https://doi.org/10.1039/d4ob01539h","url":null,"abstract":"<p><p>NMR spectral and theoretical analyses of homologous prolyl carbamates reveal subtle charge transfer tetrel bonding interactions (TBIs), selectively stabilizing their <i>cis</i>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 <i>cis</i>Pro motif. The number of TBIs and hence the <i>cis</i>Pro stability increase with increasing number of C<sup>β</sup> groups at the carbamate alcohol. Increasing solvent polarities also increase the relative <i>cis</i>Pro carbamate stabilities.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-28","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
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":null,"pages":null},"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, Götz Bucher
{"title":"Tetraarylammonium salts - synthesis, properties and emerging use.","authors":"Alexander Marriott, Götz Bucher","doi":"10.1039/d4ob01386g","DOIUrl":"https://doi.org/10.1039/d4ob01386g","url":null,"abstract":"<p><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 <i>tour de force</i>, 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":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","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":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
首页 上一页 下一页 尾页
0
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整，为了账户安全，请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
请完成安全验证×
相关产品
×
本文献相关产品
联系我们：info@booksci.cn Book学术提供免费学术资源搜索服务，方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号：481959085
Book学术官方微信