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Correction: Nitrogen migration for amino acid synthesis: enzymes take control 修正：氨基酸合成的氮迁移：酶起控制作用
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-19 DOI: 10.1039/d6qo90077a
Lilu Zhang,Eric Meggers
{"title":"Correction: Nitrogen migration for amino acid synthesis: enzymes take control","authors":"Lilu Zhang,Eric Meggers","doi":"10.1039/d6qo90077a","DOIUrl":"https://doi.org/10.1039/d6qo90077a","url":null,"abstract":"Correction for ‘Nitrogen migration for amino acid synthesis: enzymes take control’ by Lilu Zhang et al., Org. Chem. Front., 2026, https://doi.org/10.1039/d6qo01348a.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"11 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149218267","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
Theoretical Insights into Lewis Acid-Promoted C-C Bond Cleavage in Ni-Catalyzed Cyclobutanone Activation via Sequential Insertion/β-Carbon Elimination 通过顺序插入/β-碳消除，Lewis酸促进的C-C键切割在ni催化环丁酮活化中的理论见解
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-19 DOI: 10.1039/d6qo01279e
Li-Li Liao,Hui-Lin Luo,Yu-Fu Gao,Li-Cai Liu,Chuan-Kun Ran,Chuan-Xi Nie,Yi-Fei Chen,Zhen Zhang,Xiangge Zhou,Da-Gang Yu
{"title":"Theoretical Insights into Lewis Acid-Promoted C-C Bond Cleavage in Ni-Catalyzed Cyclobutanone Activation via Sequential Insertion/β-Carbon Elimination","authors":"Li-Li Liao,Hui-Lin Luo,Yu-Fu Gao,Li-Cai Liu,Chuan-Kun Ran,Chuan-Xi Nie,Yi-Fei Chen,Zhen Zhang,Xiangge Zhou,Da-Gang Yu","doi":"10.1039/d6qo01279e","DOIUrl":"https://doi.org/10.1039/d6qo01279e","url":null,"abstract":"Direct oxidative addition and β-carbon elimination are the two fundamental pathways for the transition metal (TM)-catalyzed carbon-carbon (C–C) bond activation. Despite significant progress, how cyclobutanone frameworks switch between the distinct C–C bond activation modes remains insufficiently understood. Herein, density functional theory (DFT) calculations were performed to elucidate the mechanistic role of Lewis acid in modulating activation pathways and promoting C–C bond cleavage during the Ni-catalyzed ring-opening/reductive carboxylation of ortho-bromo-3-phenylcyclobutanones with CO2. This reaction initiates via C–Br bond oxidative addition to Ni(0) center followed by reduction to give the aryl-Ni(I) species. For the subsequent C–C bond activation, coordination of a Lewis acid to the carbonyl oxygen of cyclobutanone shifts the mechanistic preference from conventional C–C bond oxidative addition to a sequential migratory insertion/β-carbon elimination pathway. Frontier molecular orbital (FMO) analysis and global reactivity index (GRI) analysis indicate that Lewis acid coordination significantly lowers the LUMO energy of the carbonyl (C=O) moiety, markedly enhancing its electrophilicity. Further geometry analysis, interaction region indicator (IRI) analysis, and energy decomposition analysis (EDA) reveal that the Lewis acid stabilizes the key insertion transition state through favorable non-covalent interactions specifically involving C–H•••Cl and lone pair•••π interactions, dominated primarily by electrostatic and orbital interactions. Subsequent Lewis acid-promoted CO2 insertion and reduction take place, affording final carboxylated product and regenerating Ni(0) complex. These findings not only elucidate the pivotal role of Lewis acid in cyclobutanone activation but also offer valuable guidelines for designing Lewis-acid-assisted C–C bond cleavage and cross-coupling reactions.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"37 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149218263","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
Diastereodivergent azetidine synthesis anion-relay-chemistry-enabled [2 + 2] cycloaddition of alkynes with -aryl imines 非对映发散氮杂啶的合成阴离子接力化学使[2 + 2]炔与-芳基亚胺的环加成
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-19 DOI: 10.1039/d6qo01012a
Xiaomeng Gong,Yingying Xue,Zhuzhu Zhang,Guohong Tang,Xiangrong Xu,Liang Li,Ruipeng Li,Shouchu Tang
{"title":"Diastereodivergent azetidine synthesis anion-relay-chemistry-enabled [2 + 2] cycloaddition of alkynes with -aryl imines","authors":"Xiaomeng Gong,Yingying Xue,Zhuzhu Zhang,Guohong Tang,Xiangrong Xu,Liang Li,Ruipeng Li,Shouchu Tang","doi":"10.1039/d6qo01012a","DOIUrl":"https://doi.org/10.1039/d6qo01012a","url":null,"abstract":"Azetidines are privileged structural motifs in medicinal chemistry, yet diastereodivergent synthesis of highly substituted variants from simple precursors remains elusive. Herein, we report an anion-relay-chemistry (ARC)-enabled [2 + 2] cycloaddition of alkynyl 1,3-dithianes with N-aryl imines. Crucially, the 1,3-dithiane unit serves as an anion-stabilizing structural element that enables the carbanionic relay process while remaining a synthetically versatile sulfur-containing handle. This strategy bypasses the limitations of conventional photocycloadditions and enables access to a previously inaccessible reactivity mode. Notably, base loading precisely controls diastereochemical outcomes, allowing programmable synthesis of either cis- or trans-azetidines from identical substrates. The protocol proceeds under mild conditions, exhibits a broad substrate scope, and delivers densely functionalized products in good yields with excellent selectivity. The resulting azetidines serve as versatile intermediates for rapid access to β-lactams and β-aminoketones. This work establishes a general platform for stereodivergent azetidine synthesis.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"4 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149218264","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
Electrosynthesis of 1H-and 2H-Indazoles by Reduction of o-Nitrobenzylamines, a Versatile and Sustainable Access 邻硝基苄胺还原电合成1h -和2h -吲哚，一种通用和可持续的方法
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-19 DOI: 10.1039/d6qo01360k
Eric F. R. Pertermann,Daniel Doellerer,Claudia M Kammler,Thomas Weyhermueller,Sebastian Beil,Bernd Werner,Siegfried R. Waldvogel
{"title":"Electrosynthesis of 1H-and 2H-Indazoles by Reduction of o-Nitrobenzylamines, a Versatile and Sustainable Access","authors":"Eric F. R. Pertermann,Daniel Doellerer,Claudia M Kammler,Thomas Weyhermueller,Sebastian Beil,Bernd Werner,Siegfried R. Waldvogel","doi":"10.1039/d6qo01360k","DOIUrl":"https://doi.org/10.1039/d6qo01360k","url":null,"abstract":"Indazoles represent an important pharmacologically active class of compounds. However, reliable and sustainable pathways from simple substrates remain scarce. We report an easily applicable and sustainable electrochemical synthesis of various 1H-and 2H-indazoles via direct reduction of o-nitrobenzylamines, avoiding stoichiometric reagents and elevated temperatures. The protocol enables access to 50 distinct structures with isolated yields up to 96% and a broad tolerance for functional groups and heterocycles. Additionally, we demonstrate electrochemical post-functionalization, access to APIs and their precursors, as well as robust scalability.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"1 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149218266","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
Palladium-Catalyzed Multi-Fold Domino Cyclization for Access to N-Doped PAHs; Recyclable [Pd]-System, Light Emitting Applications 钯催化多重多米诺环化制备n掺杂多环芳烃可回收[Pd]-系统，发光应用
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-16 DOI: 10.1039/d6qo01172a
Jakkula Naveen,Satyanarayana Gedu
{"title":"Palladium-Catalyzed Multi-Fold Domino Cyclization for Access to N-Doped PAHs; Recyclable [Pd]-System, Light Emitting Applications","authors":"Jakkula Naveen,Satyanarayana Gedu","doi":"10.1039/d6qo01172a","DOIUrl":"https://doi.org/10.1039/d6qo01172a","url":null,"abstract":"Herein, we report an efficient, sustainable, and green domino strategy for the divergent synthesis of N-doped indeno[1,2-c]pyrrolo[3,2,1-ij]quinoline derivatives, first of their kind from 2,6-bis(arylethynyl)anilines under PEG-400/palladium-recyclable conditions via four to five new chemical bonds in a single process. The Pd-catalyst/PEG-400 was recycled and reused for up to four consecutive cycles. The protocol demonstrates excellent functional-group tolerance and a broad substrate scope, while its synthetic utility is highlighted by successful scale-up reactions and the incorporation of drug-derived substrates. Importantly, the resulting compounds display strong orange-red fluorescence, as evidenced by UV-visible absorption, fluorescence, lifetime, and quantum yield analyses. Notably, LED-coating experiments revealed that blue LEDs coated with these compounds emit orange-red light, underscoring their promising potential as orange-red light-emitting materials.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"27 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149173214","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
Synthesis of Polyhydroxyalkyl Oxazoles from Unprotected Aldoses and Tetramethylguanidine 无保护醛糖和四甲基胍合成多羟基烷基恶唑
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-16 DOI: 10.1039/d6qo01251e
Mian Liu,Lianyou Zheng,Junxiang Bai,Qiansong Gao,Zhuoqi Zhang,Lingling Shi,Jinbao Xiang
{"title":"Synthesis of Polyhydroxyalkyl Oxazoles from Unprotected Aldoses and Tetramethylguanidine","authors":"Mian Liu,Lianyou Zheng,Junxiang Bai,Qiansong Gao,Zhuoqi Zhang,Lingling Shi,Jinbao Xiang","doi":"10.1039/d6qo01251e","DOIUrl":"https://doi.org/10.1039/d6qo01251e","url":null,"abstract":"A facile one-pot approach has been developed for the synthesis of polyhydroxyalkyl oxazoles directly from unprotected aldoses and tetramethylguanidine (TMG), using n-Bu₄NOAc as the additive under mild heating. The protecting-group-free process features operational simplicity and broad substrate scope. This method provides direct access to valuable polyhydroxyalkyl oxazoles and offers a practical strategy for the direct derivatization of carbohydrate feedstocks.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"15 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149173212","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
Mechanistic Origin of TBAI-Controlled Regioselectivity Reversal in the Palladium-Catalyzed Hydrocarboxylation of Terminal Aryl Alkynes with Oxalic Acid 钯催化末端芳基炔与草酸羟基化反应中tbai控制区域选择性逆转的机理
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-16 DOI: 10.1039/d6qo01302c
Yishi Li,Jianqi Chen,Xuyu Qin,Juan Li
{"title":"Mechanistic Origin of TBAI-Controlled Regioselectivity Reversal in the Palladium-Catalyzed Hydrocarboxylation of Terminal Aryl Alkynes with Oxalic Acid","authors":"Yishi Li,Jianqi Chen,Xuyu Qin,Juan Li","doi":"10.1039/d6qo01302c","DOIUrl":"https://doi.org/10.1039/d6qo01302c","url":null,"abstract":"Regiodivergent hydrocarboxylation of terminal alkynes provides efficient access to branched and linear α,β-unsaturated carboxylic acids, yet the mechanistic origin of additive-controlled regioselectivity remains unclear. Here, density functional theory calculations reveal how tetrabutylammonium iodide (TBAI) reverses the regioselectivity of Pd/Xantphos-catalyzed hydrocarboxylation of terminal aryl alkynes with oxalic acid. In the absence of TBAI, oxalic acid directly protonates the terminal carbon of the Pd-bound alkyne in concert with Pd–C bond formation, whereas pathways involving water as the immediate proton donor or a discrete Pd–H intermediate are disfavored. This distortion-controlled proton-transfer/palladation pathway selectively generates the branched alkenylpalladium intermediate. In the presence of TBAI, iodide coordination alters the catalyst speciation and enables formation of an iodide-ligated Pd–H species followed by regioselective hydropalladation, thereby producing the linear alkenylpalladium intermediate. In both cases, subsequent carbonylation proceeds preferentially through direct migratory CO insertion, followed by hydrogen oxalate-assisted hydrolysis. The calculated hydrolysis barriers qualitatively reproduce the experimental substrate- and ligand-dependent yield trends. Distortion–interaction and noncovalent-interaction analyses further associate the substrate effects primarily with structural distortion and the superior performance of Xantphos with its rigid, preorganized coordination environment. These findings establish iodide-induced catalyst speciation and pathway switching as the origin of the regioselectivity reversal and provide mechanistic guidance for controlling Pd-catalyzed regiodivergent hydrocarboxylation.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"107 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149173213","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
Expression of concern: Dithiocarbamate mediated thioamidation C–C single bond cleavage of styrene: study of the protocol in decarbonylative and decarboxylative thioamidations 关注表达：二硫代氨基甲酸酯介导的硫胺化：苯乙烯的C-C单键裂解：脱羰和脱羧硫胺化的协议研究
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-15 DOI: 10.1039/d6qo90072k
Debabrata Patra,Amit Saha
{"title":"Expression of concern: Dithiocarbamate mediated thioamidation C–C single bond cleavage of styrene: study of the protocol in decarbonylative and decarboxylative thioamidations","authors":"Debabrata Patra,Amit Saha","doi":"10.1039/d6qo90072k","DOIUrl":"https://doi.org/10.1039/d6qo90072k","url":null,"abstract":"Expression of concern for ‘Dithiocarbamate mediated thioamidation via C–C single bond cleavage of styrene: study of the protocol in decarbonylative and decarboxylative thioamidations’ by Debabrata Patra et al., Org. Chem. Front., 2024, 11, 1150–1156, https://doi.org/10.1039/D3QO01921G.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"408 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149173215","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
Construction of Supramolecular Polymers and Structural Transformation Based on Multiple Noncovalent Interactions 基于多重非共价相互作用的超分子聚合物的构建与结构转化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-14 DOI: 10.1039/d6qo01188h
Linlin Liu,Yan Zhang,Yuzhen Wang,Tiantian Miao,Zhihao Xu,Hui Li
{"title":"Construction of Supramolecular Polymers and Structural Transformation Based on Multiple Noncovalent Interactions","authors":"Linlin Liu,Yan Zhang,Yuzhen Wang,Tiantian Miao,Zhihao Xu,Hui Li","doi":"10.1039/d6qo01188h","DOIUrl":"https://doi.org/10.1039/d6qo01188h","url":null,"abstract":"In this work, we report the construction and structural transformation of new supramolecular polymers. Four monomers, M1, M2, M3 and M4, were designed and synthesized. M1, M3, M4 and Zn(OTf)2 can self-assemble into supramolecular linear polymers (SLP) through pillararene-based host–guest interaction and terpyridine-based complementary metal coordination. Upon addition of monomer M2 to the SLP solution, the SLP further transformed into supramolecular cross-linked polymers (SCP) via crown ether-based host–guest interaction. Furthermore, the obtained SCP formed a supramolecular polymer gel at high concentrations, and the reversible gel–sol transformation could be realized in response to multiple stimuli. This research provides inspiration for the design and preparation of supramolecular polymers with different topological structures.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"10 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149173210","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
Pressure-induced dearomative cycloadditions of trialkylsilyloxy-substituted dienes to nitroheteroarenes 压力诱导三烷基硅氧基取代二烯对硝基杂芳烃的脱芳环加成
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-14 DOI: 10.1039/d6qo01106c
Nathan Noël,Yun Liu,Tianyu Zhang,Laëtitia Chausset-Boissarie,Armin R. Ofial,Isabelle Chataigner
{"title":"Pressure-induced dearomative cycloadditions of trialkylsilyloxy-substituted dienes to nitroheteroarenes","authors":"Nathan Noël,Yun Liu,Tianyu Zhang,Laëtitia Chausset-Boissarie,Armin R. Ofial,Isabelle Chataigner","doi":"10.1039/d6qo01106c","DOIUrl":"https://doi.org/10.1039/d6qo01106c","url":null,"abstract":"Complex polycyclic structures can rapidly be constructed by dearomative (4 + 2) cycloadditions. We show that combining electron-rich (nucleophilic) trialkylsiloxy-activated dienes with electron-poor (electrophilic) indoles, azaindoles, benzofurans, and benzothiophenes at high pressure (16 kbar) is a versatile approach to construct products with bi-, tri-, and tetracarbo- or heterocyclic scaffolds diastereoselectively in one step and without the use of catalysts. The reactivity descriptors N, sN and E as defined by the Mayr–Patz equation, lg k20°C = sN(N + E), were determined for the trialkylsiloxy-dienes (N and sN) and dienophiles (E) by using (stopped-flow) photometric techniques to follow the kinetics of their reactions with reference compounds. The cycloaddition performance in reactions of the trimethylsiloxy-dienes follows the trend of their nucleophilicity (N). The mechanism of the cycloaddition of the prototypical dienophile N-Boc-7-aza-3-nitroindole with 2-(trimethylsiloxy)-buta-1,3-diene was further scrutinized by quantum-chemical methods.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"15 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149173216","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
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