Organic Chemistry Frontiers最新文献

{"title":"Acceptor-Driven Structural Modulation of Tetraphenylphenylenediamine-Based Donor-Acceptor Architectures for Non-Volatile Resistive Memory Devices","authors":"Senthilkumar V Swetha,Murali Ardra,P. K. M. Imran,Samuthira Nagarajan","doi":"10.1039/d6qo01154c","DOIUrl":"https://doi.org/10.1039/d6qo01154c","url":null,"abstract":"Building upon the donor-acceptor design principle, a series of six new compounds was designed and synthesised by integrating a tetraphenylphenylenediamine (TPPA) electron donor moiety coupled with the structurally diverse quinoxalinebased electron acceptor moiety to probe the impact of structural modulation on resistive memory device performance. A comprehensive structure-property relationship was established through photophysical studies, thin-film morphology, density functional theory (DFT) calculations, and memory characteristics. The synthesised compounds exhibited pronounced intramolecular charge transfer with broad visible absorption and a narrow optical band gap of 2.6-2.9 eV, demonstrating the efficient nature of D-A segments. FESEM and AFM analyses revealed continuous, homogeneous thin films with interconnected molecular packing, providing favorable pathways for charge transport. The fabricated devices exhibited excellent non-volatile resistive switching characteristics, including low operating voltages (-1.19 to -1.49 V), an ON/OFF current ratio of 10 3 -10 4 , stable data retention exceeding 5 s, and reliable endurance over 10² switching cycles, with negligible device-to-device variation. Remarkably, the dimethoxydiphenyl-substituted quinoxaline derivative exhibited ternary writeonce-read-many (WORM) memory behaviour, whereas the remaining derivatives demonstrated binary WORM characteristics. The results were further substantiated by DFT calculations, which revealed efficient intramolecular charge transfer between the donor TPPA and acceptor quinoxaline moiety. By systematically tailoring the quinoxaline acceptor unit, this work demonstrates how subtle molecular modifications can precisely regulate structural and memory properties. The insights provided a fundamental framework for the rational design of D-A molecular systems for efficient, stable, and low operating-voltage organic non-volatile memory devices.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"42 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149225873","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}

{"title":"Chemoselective three-component biheterocyclization-chalcogenation of two distinct isocyanides with chalcogen nucleophiles for modular synthesis of 4-chalcogenylated pyrrolo[2,3-c]quinolines","authors":"Jinhuan Dong,Shangying Qiao,Lianshun Zhang,Wei Yang,Xianxiu Xu","doi":"10.1039/d6qo01195k","DOIUrl":"https://doi.org/10.1039/d6qo01195k","url":null,"abstract":"The two-component cross-heterocyclization of α-acidic isocyanides has proven to be an efficient method for constructing various mono- or bi-heterocyclic scaffolds. However, the multicomponent biheterocyclization of two different isocyanides remains challenging due to their propensity for side reactions. Herein, we report the first example of a highly chemoselective three-component biheterocyclization-chalcogenation of two distinct isocyanides and readily available chalcogen nucleophiles, providing straightforward access to diverse 4-chalcogenylated pyrrolo[2,3-c]quinolines. Furthermore, gram-scale synthesis and several transformations of the resulting product underscore the synthetic utility of the developed methodology.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"64 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149225918","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}

{"title":"Synthesis of α‑BCP carbonyls through visible‑light‑driven hydroalkylation of [1.1.1]propellane","authors":"Yating Du,Xinchang Wang,Xiaoyang Yao,An Chen,Pengfei Zhang,Jun Xu","doi":"10.1039/d6qo01153e","DOIUrl":"https://doi.org/10.1039/d6qo01153e","url":null,"abstract":"Herein, we report a visible-light-mediated hydroalkylation of [1.1.1]propellane with α-bromocarbonyl compounds using a metal-free photoredox catalytic system. This protocol operates under exceptionally mild conditions and accommodates a broad range of esters, amides, and ketones, delivering the corresponding BCP adducts in moderate to excellent yields. Experimental and computational mechanistic studies support a radical pathway initiated by single-electron transfer from the photocatalyst, followed by radical addition to [1.1.1]propellane and subsequent hydrogen atom transfer from the solvent. The synthetic utility of this approach is further underscored by its scalability and its compatibility with complex molecular scaffolds. This strategy provides a modular and efficient entry to structurally diverse BCP derivatives, offering promising opportunities for drug discovery and advanced synthesis.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"2 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149225872","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}

{"title":"Recent advances in electrocatalytic multicomponent reactions for synthesizing organic chalcogenide compounds","authors":"Miao-Ying Wang,Fei-Hu Cui,Hai-Tao Tang,Ying-Ming Pan","doi":"10.1039/d6qo01329e","DOIUrl":"https://doi.org/10.1039/d6qo01329e","url":null,"abstract":"Chalcogen-containing compounds serve as essential scaffolds in drugs and natural products. Electrocatalytic multicomponent reactions offer a sustainable strategy for constructing organosulfur, organoselenium, and organotellurium compounds. By leveraging electrons as clean reactants, this method eliminates the need for additional chemical oxidants, reducing waste generation and environmental footprint. Precise regulation of reaction potential and current density enables adjustable reaction pathways, which improves reaction selectivity, efficiency and product purity. This review focuses on electrocatalytic multicomponent reactions for the synthesis of organic chalcogenide compounds, with emphasis on reaction design, process optimization, substrate scope and the mechanism of selectivity. It also discusses catalyst development and stability for sulfur, selenium and tellurium-based reaction systems. Current challenges, including limited substrate compatibility, catalyst deactivation and large-scale synthesis difficulties, are also analyzed. Future research directions include developing more efficient electrocatalysts, expanding applications in pharmaceutical synthesis, and integrating the method with renewable energy sources. The insights presented in this review are intended to guide the green and efficient synthesis of valuable organochalcogen compounds, and contribute to the development of sustainable organic chemistry.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"12 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149218265","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}

{"title":"Organophotocatalytic cascade reaction of 3-aza-1,5-dienes for the synthesis of α,β-unsaturated γ-lactams","authors":"Ziyu Jin,Yuping Xiong,Jian-Qiang Chen,Jie Wu","doi":"10.1039/d6qo01226d","DOIUrl":"https://doi.org/10.1039/d6qo01226d","url":null,"abstract":"We report an efficient and facile synthetic protocol for the synthesis of various α,β-unsaturated γ-lactams via photocatalyzed radical addition/cyclization/isomerization under metal-free conditions. This cascade reaction is compatible with various radical precursors, including alkyl chlorooxoacetates, aroyl chlorides, sulfonyl chlorides, and α-bromocarbonyl compounds, enabling the facile access to ester-, aroyl-, sulfonyl-, and alkyl-substituted α,β-unsaturated γ-lactams. This method features mild reaction conditions, inexpensive organic photocatalyst, and operational simplicity.Nitrogen-containing heterocycles are undoubtedly among the most important structural motifs, as they are widely applied in the fields of pharmaceuticals, 1 agrochemicals, 2 functional materials, 3 ligands, 4 and homogeneous organic catalysts. 5 Approximately 60% of small-molecule drugs contain one or more N-heterocyclic moieties. 1 Moreover, statistical analysis indicates that this structural motif is present in 90% of the top 50 best-selling small-molecule drugs in 2024. 6 As an important subset of these nitrogen-containing heterocycles, α,β-unsaturated γ-lactams serve as a privileged structural scaffold in numerous bioactive compounds and also find widespread applications in pharmaceuticals. Several representative examples are illustrated in Fig. 1a. 7 For instance, palmyrrolinone, a metabolite isolated from cyanobacterial extracts, exhibits significant toxicity against Biomphalaria glabrata. 7a Denigrin F is an alkaloid isolated from a marine sponge and features a highly substituted α,β-unsaturated γlactam as its core structural motif. 7b Imrecoxib and glimepiride are clinically approved anti-inflammatory and antidiabetic agents, respectively. 7d Furthermore, α,β-unsaturated γ-lactams are versatile synthons for the synthesis of saturated γ-lactams, which are important structural elements in both natural products and bioactive molecules. 8 Therefore, numerous strategies have been developed for the synthesis of α,βunsaturated γ-lactams, 9 including the classical aza-Pauson-Khand reaction, 9a,b single-carbon atom doping cyclization of acrylamides, 9c and reductive carboxylation of propargyl amines. 9d Despite these advances, most of these methods still require transition-metal catalysts, high reaction temperature, or strong acid/base conditions, which limits their large-scale synthesis and industrial applications.Recently, aza-1,5-dienes have been found to be suitable substrates for the construction of various nitrogen-containing heterocycles. 10 Murarka, 10a Wu, 10b Liang, 10c Wu, 10d,e Selvakumar, 10f and their coworkers have reported the radical addition/cyclization of the corresponding aza-1,5-dienes for the","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"33 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149225874","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}

{"title":"Photoinduced Selective Perfluoroalkylation of Aldehyde for the Synthesis of Perfluoroalkylated Alkenes","authors":"Yi Chen,Zhen Liang,Sudan Tong,Jianwei Yan,Aifang Wang,Chao Shen,Min Wang,Jiabin Shen","doi":"10.1039/d6qo01266c","DOIUrl":"https://doi.org/10.1039/d6qo01266c","url":null,"abstract":"A new photocatalytic radical addition-elimination reaction has been described that allows readily accessible aldehyde, dimethyl sulfoxide and perfluoroalkyl iodides to provide perfluoroalkylated alkenes with good E-stereoselectivities. This protocol features mild and green conditions, operational simplicity, broad substrate scope and appreciable functional group tolerance, thus providing a sustainable and environment-friendly means of directly installing fluoroalkyl groups (-C4F9, -C10F21, -C6F12I, -CF2COOR, etc.) in organic frameworks.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"3 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149225879","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}

{"title":"A Difluorocarbene Activated Dearomatization-Rearomatization Platform for Late-Stage C4-Functionalization of Pyridine Skeleton","authors":"Zheng-Wen Liang,Xingwei Xun,Xi-Cun Wang,Dong-ping Chen,Zheng-Jun Quan","doi":"10.1039/d6qo01372d","DOIUrl":"https://doi.org/10.1039/d6qo01372d","url":null,"abstract":"C4-Functionalized pyridine skeletons are privileged structures in pharmaceuticals and materials, yet direct, highly selective C4-functionalization remains challenging due to poor selectivity and limited substrate scope. Herein, we describe a difluorocarbene (DFC)-activated strategy that enables direct and tunable C4-functionalization under mild, metal-free conditions. The method relies on in situ formation of N-difluoromethylpyridinium ylides, wherein the strong electronwithdrawing effect of DFC directs nucleophilic addition exclusively to the C4 position. The resulting N-formyl-1,4dihydropyridines (N-CHO-1,4-DHPs) are stable and serve as versatile intermediates for subsequent reactions with diverse P-, N-, S-, and C-based nucleophiles, exhibiting broad functional group tolerance and excellent regioselectivity across a wide range of pyridine and quinoline substrates, including drug-molecule post-modifications. Acid-mediated hydrolysis of the N-CHO-1,4-DHP intermediates, without isolation, directly provides C4-functionalized aromatic products. Control experiments and DFT calculations shed light on the reaction mechanism.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"15 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149225875","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}

{"title":"Rh(III)-Catalyzed Synthesis of Benzotriazinone-Peptide Conjugates via C(sp²)-H Alkenylation of Alkenyl-Tethered Peptides","authors":"Ting-Ting Feng,Lin Dong,Lin Xiao,Xingxing Ding","doi":"10.1039/d6qo01245k","DOIUrl":"https://doi.org/10.1039/d6qo01245k","url":null,"abstract":"This paper describes a Rh(III)-catalyzed C(sp²)-H alkenylation of 1,2,3-benzotriazinones with acryloyl amino acids, long-chain unsaturated amino acids, and peptides, enabled by the benzotriazinone directing group. The protocol features broad substrate scope and complete stereochemical retention. Notably, this work represents the first direct coupling of benzotriazinones with amino acids and peptides bearing alkenyl side chains. Furthermore, alkylated alanine derivative and denitrogenated benzamide product can be selectively obtained by tuning the reaction conditions.1,2,3-Benzotriazinones represent a privileged class of heterocyclic scaffolds, which have attracted tremendous research interest by diverse biological activities and extensive synthetic applicability. Derivatives of 3-phenylbenzo [d][1,2,3]triazin-4(3H)-one display a broad spectrum of biological activities including diuretic, 1 anticancer, 2 antidepressant, 3 antiviral, 4 antituberculous 5 and anesthetic 6 effects, making them highly valuable for research in the field of medicinal chemistry (Figure 1a). It is evident that these appealing properties have prompted substantial efforts to modify the structure of benzotriazinones, with the objective of generating versatile derivatives that improved performance and structural diversity.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"67 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149225913","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}

{"title":"Rapid construction of the Tetracyclic Skeleton of Cephalocyclidin A","authors":"Yangtian Yan,Xu Yan,Zhaoyang Li,Yiwei Xu,Xiaohan Xu,Fang Wang,Yang Yang","doi":"10.1039/d6qo01319h","DOIUrl":"https://doi.org/10.1039/d6qo01319h","url":null,"abstract":"The stereoselective synthesis of the tetracyclic skeleton of cephalocyclidin A, an alkaloid with a fused-pentacyclic ring system, is reported. The key to the synthesis of the skeleton is a Cu-catalyzed [3 + 2] cycloaddition that enables the convergent assembly of functionalized fragments. The core skeleton of cephalocyclidin A was constructed via Pd-catalyzed intramolecular direct arylation.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"34 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149225870","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}

{"title":"Yb(OTf)3 -Catalyzed Double Ring-Opening of Bicyclo[1.1.0]butanes with N-Vinyl Nitrones to Prepare N-Cyclobutyl 2-Oxa-3-azabicyclo[3.1.1]heptanes","authors":"Yao-Yao Liang,Shi-Yu Deng,Yang Chen,Xin-Yin Liang,Guo-Ao Wang,Wen-Bo Zhang,Xiao-Hua Li,Qing-Qing Liu,Xue-Ling Mo,Dong-Liang Mo","doi":"10.1039/d6qo01267a","DOIUrl":"https://doi.org/10.1039/d6qo01267a","url":null,"abstract":"Herein, a variety of N-cyclobutyl 2-oxa-3-azabicyclo[3.1.1]heptanes were prepared in moderate to good yields (21%-84%) and high diastereoselectivity (2.7:1 to >20:1) through Yb(OTf)3-catalyzed double ring-opening of bicyclo[1.1.0]butanes with cinnamaldehyde-derived N-vinyl nitrones under mild reaction conditions. Mechanistic studies revealed that the reaction underwent a cascade of (3+3) cycloaddition, deolefination, and second ring-opening of BCBs. More importantly, chiral N-cyclobutyl 2-oxa-3-azabicyclo[3.1.1]heptanes could be achieved by Lewis acid and chiral phosphoric acid catalysts, respectively. The present method features double ring-opening of BCBs in a one pot, imidazole group-directed (3+3) cycloaddition, and novel N-cyclobutyl 2-oxa-3-azabicyclo[3.1.1]heptane scaffolds.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"8 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149225914","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}