Organic Chemistry Frontiers最新文献_第2页

Rh2(II)-catalyzed cyclization/gem-hydrosilylation of benzene-fused 1,6-enynones Rh2（II）催化苯融合1,6-烯酮的环化/宝石硅氢化反应

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-07-22 DOI: 10.1039/d5qo00835b

Zurong Xu, Jiajun Lu, Rui Wu, Shifa Zhu

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An umpolung of transient arylidene malonates via photoactivated one-electron reduction: the application to the catalyst-free multicomponent synthesis of imidazolinone malonic acids 光激活单电子还原法对瞬态丙二酸芳基芳基的研究：在咪唑啉酮丙二酸无催化剂多组分合成中的应用

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-07-21 DOI: 10.1039/d5qo00768b

Aidar Z. Kamaletdinov, Elizaveta A Kuznetsova, Andrey V Smolobochkin, Almir Gazizov, Tatyana Gerasimova, Aliya Saitova, Anna Strelnik, Victor Vasil'evich Syakaev, Sergey Efimov, Vladimir Klochkov, Olga Babaeva, Vasily Babaev, Lyubov V Frantsuzova, Daria P. Gerasimova, Mikhail Khrizanforov, Alexander Burilov, Michail Pudovik

{"title":"An umpolung of transient arylidene malonates via photoactivated one-electron reduction: the application to the catalyst-free multicomponent synthesis of imidazolinone malonic acids","authors":"Aidar Z. Kamaletdinov, Elizaveta A Kuznetsova, Andrey V Smolobochkin, Almir Gazizov, Tatyana Gerasimova, Aliya Saitova, Anna Strelnik, Victor Vasil'evich Syakaev, Sergey Efimov, Vladimir Klochkov, Olga Babaeva, Vasily Babaev, Lyubov V Frantsuzova, Daria P. Gerasimova, Mikhail Khrizanforov, Alexander Burilov, Michail Pudovik","doi":"10.1039/d5qo00768b","DOIUrl":"https://doi.org/10.1039/d5qo00768b","url":null,"abstract":"The Meldrum’s acid-based multi-component reactions have emerged as a highly versatile and valuable tool, offering a simple access to numerous classes of pharmaceutically and industrially valuable heterocyclic and acyclic organic compounds. The vast majority of these reactions employ a carbonyl compound as one of reagents and utilize the electrophilic reactivity of transient arylidene malonates. This necessarily requires a third nucleophilic reagent and represents the general limitation of these reactions. Herein we propose the approach to a reactivity umpolung of arylidene malonates via visible light-driven SET/PT sequence, which enables the radical chemistry in Meldrum’s acid-based MCRs. The viability of the proposed approach is demonstrated by the three-component synthesis of hitherto unknown imidazolinone malonic acids. The radical chain mechanism is evidenced for the disclosed transformation by mechanistic experiments and density functional calculations.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"37 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144678254","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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Quinoline-Substituted Excited-State Intramolecular Proton Transfer Fluorophores as Stimuli-Sensitive Dual-State Fluorophores 喹啉取代激发态分子内质子转移荧光团作为刺激敏感双态荧光团

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-07-21 DOI: 10.1039/d5qo00639b

Timothée Stoerkler, Gilles Ulrich, Adèle D Laurent, Denis Jacquemin, Julien Massue

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Zwitterionic triple- and quadruple hydrogen-bonding motifs 两性离子的三重和四重氢键基序

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-07-21 DOI: 10.1039/d5qo00874c

Qixun Shi, Kai Liu, Chuang Ye, Augustina Jozeliūnaitė, Vytautas Klimavičius, Jas S. Ward, Kari Rissanen, Edvinas Orentas

{"title":"Zwitterionic triple- and quadruple hydrogen-bonding motifs","authors":"Qixun Shi, Kai Liu, Chuang Ye, Augustina Jozeliūnaitė, Vytautas Klimavičius, Jas S. Ward, Kari Rissanen, Edvinas Orentas","doi":"10.1039/d5qo00874c","DOIUrl":"https://doi.org/10.1039/d5qo00874c","url":null,"abstract":"Zwitterionic triple and quadruple hydrogen-bonding heterocyclic modules based on an easily accessible deazapterin scaffold are reported. The solid-state structure of 3H-bonding zwitterionic molecules revealed the formation of various hydrogen-bonded 1D chains composed of water, methanol, or a chloride anion, depending on the extent of protonation. The association of newly designed AAD and AADA (D = hydrogen-bond donor, A = hydrogen-bond acceptor) zwitterionic monomers was studied in solution to identify complementary partners and to evaluate binding strength. Both AAD and AADA motifs form 3H-bonded dimers after the addition of half an equivalent of acid, representing a negatively-charged analogue of the C–C<small><sup>+</sup></small> pair in naturally occurring DNA i-motifs. The protonation of the AADA motif with hydrochloric acid converts it into a non-H-bonding form where the urea moiety is complexed with the chloride anion. The exchange of chloride with non-nucleophilic anions unlocks the rotation of the urea group, resulting in the formation of the ADDA–DAAD heterocomplex with 2,7-diamido-1,8-naphthyridine.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"118 Suppl 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144669973","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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Visible-light induced C(sp3)–S cross-coupling via electron donor–acceptor complexes and 1,2-hydrogen atom transfer 可见光诱导C(sp3) -S通过电子供体-受体配合物交叉偶联和1,2-氢原子转移

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-07-21 DOI: 10.1039/d5qo00824g

Xue Zhang, Liulin Jiao, Jian Chen, Hongying Fan, Jinyu Hou, Guanghui Lv, Zhongzhen Yang, Yong Wu

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Conversion of Phenols to Phosphamides and Sulfonamides through a Sequential Dearomative Functionalization followed by Reductive Coupling Strategy 通过顺序脱芳功能化和还原偶联策略将酚类转化为磷酰胺和磺胺类

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-07-19 DOI: 10.1039/d5qo00811e

Haripriya Bhumannagari, Nagaraju Rajana, Kiranmai Nayani

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Phosphorus Catalysis Enabling α-sp3-C-H Amination of 2-Alkylpyridines 磷催化使2-烷基吡啶α-sp3-C-H胺化

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-07-19 DOI: 10.1039/d5qo00960j

Yoshito Heike, Asa Tagata, Akira Yada, Kanako Nozawa-Kumada, Masaya Sawamura, Yohei Shimizu

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Exploring the intricacies of inverse hydride shuttle catalysis in azabicyclic scaffold construction with contiguous stereocenters 探索具有连续立体中心的氮杂环支架结构中反氢化物穿梭催化的复杂性

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-07-18 DOI: 10.1039/d5qo00627a

Damanpreet Kaur, Saurabh Vinod Parmar, Aniket Nigade, Vidya Avasare

{"title":"Exploring the intricacies of inverse hydride shuttle catalysis in azabicyclic scaffold construction with contiguous stereocenters","authors":"Damanpreet Kaur, Saurabh Vinod Parmar, Aniket Nigade, Vidya Avasare","doi":"10.1039/d5qo00627a","DOIUrl":"https://doi.org/10.1039/d5qo00627a","url":null,"abstract":"Asymmetric catalysis is crucial for synthetic organic chemistry, with significant implications in the synthesis of natural products and pharmaceuticals. Despite experimental advancements in the synthesis of chiral azabicyclic scaffolds using achiral organocatalysts and fluoro-aryl boranes, the fundamental mechanistic origins behind the introduction of three contiguous stereocenters remain largely unexplored. This study presents the first computational investigation into the intricacies of inverse hydride shuttle catalysis and the effect of electron-withdrawing groups in the asymmetric synthesis of azabicyclic frameworks. The condensed Fukui function analysis was employed to unravel the structure–activity relationship of five different fluoro-aryl boranes in the asymmetric synthesis of alkaloid scaffolds. The activation strain model analysis provided a quantitative assessment of contributions from interactions and deformations. The insights discovered align with experimental observations and could prove valuable in establishing efficient, selective, and sustainable methods for stereoselective synthesis without the need for any chiral source in the reaction.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"677 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144652624","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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Inorganic Reagents in photochemical Reactions 光化学反应中的无机试剂

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-07-18 DOI: 10.1039/d5qo00888c

Zhan-Yong Wang, Ziyan Zhang, Yang Liu, Yumeng Li, Xinyue Dong, Ran Xia

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Construction of Fused BN-Heterocycles via Boron Atom Insertion: DFT Insights into the Lewis Acid-Base (BBr3/NEt3) Cooperative Mechanism and Selectivity 通过硼原子插入构建融合bn -杂环：对Lewis酸碱（BBr3/NEt3）协同机制和选择性的DFT洞察

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-07-16 DOI: 10.1039/d5qo00870k

Jingxin Hu, Lin Zhang, Zexing Cao

{"title":"Construction of Fused BN-Heterocycles via Boron Atom Insertion: DFT Insights into the Lewis Acid-Base (BBr3/NEt3) Cooperative Mechanism and Selectivity","authors":"Jingxin Hu, Lin Zhang, Zexing Cao","doi":"10.1039/d5qo00870k","DOIUrl":"https://doi.org/10.1039/d5qo00870k","url":null,"abstract":"The BBr3-mediated N-heterocycle editing reaction through boron atom insertion strategy reported by Song et al. (Angew. Chem., Int. Ed. 2024, 63, e202318613), has been systematically explored by density functional theory (DFT) calculations. The present results reveal that, in addition to BBr3 acting as a boron source and nucleophile, the Lewis base NEt3 also plays a crucial role. Specifically, the Lewis acid-base cooperative interaction between BBr3 and NEt3 facilitates the ring-opening of the substrate 1-(2-vinylphenyl) azetidine, the rate-determining step of the overall cascade reaction. Notably, the organic base NEt3 facilitates the formation of the real nucleophilic species BBr4⁻, thereby promoting the progression of the reaction. Furthermore, the formation of an exceptionally stable C4NB π-ring intermediate and the difference in distortion and exchange-repulsion energies, caused by substrate structural characteristics, are responsible for chemoselectivity and regioselectivity of substrates bearing typical structural motifs and functional groups, respectively. These computational findings not only provide profound mechanistic insights into the tandem reactions involved in the construction of fused BN‐heterocycles, but also elucidate the underlying factors governing substrate preference.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"74 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144640529","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}

引用次数: 0