Organic Chemistry Frontiers最新文献_第3页

Synthesis of Cyclic Phosphonium-Borate Compounds through Reaction of Benzynes and Frustrated Lewis Pairs 通过苄基与受挫路易斯对的反应合成环状膦硼酸盐化合物

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2024-12-17 DOI: 10.1039/d4qo01852d

Pei Xie, Fang Zhang, Zhihua Cai, Yating Zheng, Leifang Wu, Lin He

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Ag(I)-linked Bis-calix[4]pyrrole Molecular Capsule and its Selective Recognition of Fluoride Anion Ag(I)-linked Bis-calix[4]pyrrole 分子胶囊及其对氟阴离子的选择性识别

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2024-12-17 DOI: 10.1039/d4qo02177k

Xiaolong Chen, Zhiye Zheng, Shunfeng Peng, Ying Guo, Ying Gao, Chenxing Guo, Jonathan L. Sessler, Hong-Yu Wang

{"title":"Ag(I)-linked Bis-calix[4]pyrrole Molecular Capsule and its Selective Recognition of Fluoride Anion","authors":"Xiaolong Chen, Zhiye Zheng, Shunfeng Peng, Ying Guo, Ying Gao, Chenxing Guo, Jonathan L. Sessler, Hong-Yu Wang","doi":"10.1039/d4qo02177k","DOIUrl":"https://doi.org/10.1039/d4qo02177k","url":null,"abstract":"A well-defined “four-wall” capsule (3) was constructed based on the coordination-driven self-assembly of a tetratopic pyridine-functionalized calix[4]pyrrole cavitand with four stabilizing pyridine···Ag+···pyridine coordination bonds in N,N-dimethylformamide (DMF). Capsule was 3 characterized by means of various techniques, including 1H nuclear magnetic resonance (NMR) spectroscopy, diffusion ordered NMR spectroscopy (DOSY), electrospray ionization mass spectrometry (ESI-MS), and single crystal X-ray diffraction analyses. The tetra-α-meso-pyridyl extended calix[4]pyrrole ligand 2 and the corresponding dimeric capsule 3 were found to recognize selectively the fluoride anion over other halide anions (chloride, bromide, and iodide anions) in DMF. Cavitand 2 was found to bind and release Ag+ via a fast equilibrium exchange process on the NMR timescale, whereas the ﬂuoride binding of both 2 and capsule 3 proved slow on the NMR timescale. The transformation among multiple molecular states, viz. monomeric form 2, capsule 3, and their corresponding fluoride-bound complexes F−⊂2 and 2F−⊂3, could be modulated by the addition of silver, fluoride, and chloride ions.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"40 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832167","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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In situ generated aza-π-allylpalladium zwitterions as nucleophilic triggers for enantioselective [4 + 2] cycloaddition with electron-deficient alkenes toward functionalized chiral piperidines 原位生成的杂氮-π-烯丙基钯齐聚物作为亲核触发器，与缺电子烯进行对映选择性[4 + 2]环加成，生成功能化手性哌啶

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2024-12-17 DOI: 10.1039/d4qo02058h

Han-Yang Zhong, Hong-Wei Xiao, Ji-Hong Liu, Zhen-Zhen Ge, Jian-Qiang Zhao, Ming-Qiang Zhou, Wei-Cheng Yuan

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Synthesis of Pyrrolo[1,2-a]quinoxalines via an Electrochemical C(sp3)-H Functionalization

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2024-12-17 DOI: 10.1039/d4qo01981d

Sijie Peng, Tong Li, Kai Li, Qi Sun, Zhiyong Wang

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Recent advances of calcium(II) triflimide in organic synthesis 三亚甲基钙（II）在有机合成中的最新进展

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2024-12-17 DOI: 10.1039/d4qo02164a

Haoran Li, Minyao Kuang, Yuwei Liu, Wei Yi, Shengdong Wang

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Tandem Synthesis of Enantioenriched Spirolactones via One-Pot Heck-Matsuda Reactions Directly from Nitroarenes 通过一锅 Heck-Matsuda 反应直接从硝基烯烃串联合成对映体丰富的螺内酯

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2024-12-17 DOI: 10.1039/d4qo01979b

Tomaz Chorro, Clemens Kaussler, Julia V. Kolodiazhnaia, Frank Jensen, Troels Skrydstrup, Carlos Roque Correia

{"title":"Tandem Synthesis of Enantioenriched Spirolactones via One-Pot Heck-Matsuda Reactions Directly from Nitroarenes","authors":"Tomaz Chorro, Clemens Kaussler, Julia V. Kolodiazhnaia, Frank Jensen, Troels Skrydstrup, Carlos Roque Correia","doi":"10.1039/d4qo01979b","DOIUrl":"https://doi.org/10.1039/d4qo01979b","url":null,"abstract":"We report herein a novel, efficient, and expeditious approach for enantioselective intramolecular carbonylative Heck-Matsuda reaction, employing highly accessible, stable, and cost-effective nitroarenes as masked electrophiles. This tandem process combines the one-pot reduction of nitroarenes to the respective anilines, diazotization, Heck-Matsuda, carbonylation, and cyclization, enabling the synthesis of enantioenriched spirolactones. The method achieves overall yields of up to 76% with excellent enantiomeric ratios of up to 96:4 under mild conditions. Isotopically labeled products are readily obtained with near stoichiometric 13C carbon monoxide. Importantly, nitroarenes are used as masked electrophiles, which serve as an advantageous alternative to anilines and aryldiazonium salts for the Heck-Matsuda reaction. This approach thereby avoids the isolation of sensitive aryldiazonium salt intermediates and, consequently, the dangers associated with them. Density Functional Theory (DFT) calculations provide precise insights into the enantioenrichment mechanism, highlighting the significance of Pd carbonyl complexes for efficient diastereoconvergence. Microkinetic modeling of the computationally obtained reaction network results in an enantioenrichment of sub-kcal-accuracy in comparison to the experiment. This work not only showcases the level of complexity achievable in the field of tandem reactions but also highlights the utility of nitroarenes in complex organic transformations, demonstrating their potential for both academic and industrial applications.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"23 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832217","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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Rhodium-Catalyzed [3 + 2] Cycloaddition of in situ Generated Nitrile Ylides with Alkenes: A Route to Quaternary 2-Trifluoromethyl-1-Pyrrolines 铑催化的原位生成腈酰与烯的[3 + 2]环加成反应：获得季 2-三氟甲基-1-吡咯烷的途径

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2024-12-17 DOI: 10.1039/d4qo01986e

Caicai He, Linxuan Li, Shuang Li, Hongzhu Chen, Hongru Zhang, Yong Wu, Xiaolong Zhang, Paramasivam Sivaguru, Karunanidhi Murali, Xihe Bi

{"title":"Rhodium-Catalyzed [3 + 2] Cycloaddition of in situ Generated Nitrile Ylides with Alkenes: A Route to Quaternary 2-Trifluoromethyl-1-Pyrrolines","authors":"Caicai He, Linxuan Li, Shuang Li, Hongzhu Chen, Hongru Zhang, Yong Wu, Xiaolong Zhang, Paramasivam Sivaguru, Karunanidhi Murali, Xihe Bi","doi":"10.1039/d4qo01986e","DOIUrl":"https://doi.org/10.1039/d4qo01986e","url":null,"abstract":"Trifluoromethylated heterocycles with a C−CF3 stereogenic center are prevalent scaffolds in many bioactive small molecules and pharmaceutical and agrochemical libraries. However, efficient methods for the construction of 2-trifluoromethyl-1-pyrroline scaffolds have remained elusive. Here we report the first rhodium-catalyzed three-component reaction of α-trifluoromethyl-N-triftosylhydrazones with nitriles and alkenes, providing rapid access to 2-trifluoromethyl-1-pyrrolines with a quaternary stereocenter from readily available starting materials. This method features mild reaction conditions, good functional group tolerance, high yields, and excellent diastereoselectivity. The synthetic utility has been further demonstrated by late-stage diversification of five complex bioactive molecules, scale-up reactions, and diverse post-synthetic transformations, yielding valuable trifluoromethylated pyrrolidine and pyrroline scaffolds. DFT calculation elucidates the origins of chemo- and diastereoselectivity and the mechanism that proceeds via the key nitrile ylide intermediate.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"253 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832218","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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Ag-Catalyzed and Difluorocarbene-Promoted Amide-Ylide Rearrangement: Synthesis of 3-Salicyloylpyridines 银催化和二氟化碳促进的酰胺-酰亚胺重排：合成 3-水杨酰吡啶

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2024-12-17 DOI: 10.1039/d4qo01961j

Xu Yuan, Tong Zhou, Qiaoqiao Wang, Yu Chen, Xiaohong Cheng, Yi Jin

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Access to Fluorinated Dienes through Hydrofluorination of 2-En-4-ynoates

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2024-12-17 DOI: 10.1039/d4qo02049a

Yue Xia, Aaron D. Charlack, Rui Guo, Nicholas W. Wade, Yiming Wang

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Modular Synthesis of β-Oxygen-containing Sulfones from Alkenes through Hexatungstate-catalyzed Cascade Hydroxysulfenylation/ Selective Oxidation

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2024-12-14 DOI: 10.1039/d4qo02151g

Xianghua Zeng, Jiaoxiong Li, Zhibin Zhou, Yongge Wei

{"title":"Modular Synthesis of β-Oxygen-containing Sulfones from Alkenes through Hexatungstate-catalyzed Cascade Hydroxysulfenylation/ Selective Oxidation","authors":"Xianghua Zeng, Jiaoxiong Li, Zhibin Zhou, Yongge Wei","doi":"10.1039/d4qo02151g","DOIUrl":"https://doi.org/10.1039/d4qo02151g","url":null,"abstract":"β-Oxygen-containing sulfones are versatile building blocks in pharmaceuticals and chemical industry. Despite notable advancements in reportedmethods, a sustainable and general catalytic method for the preparation of β-oxygen-containing sulfones remains elusive due to the inherent reactivity disparities and notorious metal-catalyst-poisoning capability of sulfur nucleophiles. Here, we present a distinct multifunctional hexatungstate catalytic strategy for the synthesis of β-hydroxy sulfones and β‑keto sulfones through a sequential hydroxysulfenylation of alkenes/selective oxidation process, utilizing a commerically available thiol and green hydrogen peroxide as the ‘oxy-sulfonylation reagent’. This method not only offers a practical route for delivering functionalized sulfones from readily available chemicals but also showcases its versatility through late-stage oxysulfonylation of complex substrates and concise syntheses of bioactive molecules. Moreover, this modular methodology features hydroperoxide reductant free, mild reaction conditions, water as the sole byproduct and new mechanism.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"22 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142820723","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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