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Photoredox-Catalyzed Stereoselective Synthesis of Allylic Amines via an Uncommon 1,2-Hydrogen Atom Transfer from Nitrogen-Centered Radicals 通过罕见的1,2-氢原子从氮中心自由基转移的光氧化还原催化立体选择性合成烯丙胺
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-14 DOI: 10.1039/d6qo01022a
Hang Wang,Sinuo Shi,Hui Song,Jing Tang,Meiling Ye,Tianle Huang,Li Hai,Jinhong Zhang,Guanghui Lv,Yong Wu
{"title":"Photoredox-Catalyzed Stereoselective Synthesis of Allylic Amines via an Uncommon 1,2-Hydrogen Atom Transfer from Nitrogen-Centered Radicals","authors":"Hang Wang,Sinuo Shi,Hui Song,Jing Tang,Meiling Ye,Tianle Huang,Li Hai,Jinhong Zhang,Guanghui Lv,Yong Wu","doi":"10.1039/d6qo01022a","DOIUrl":"https://doi.org/10.1039/d6qo01022a","url":null,"abstract":"We report a visible-light photoredox-catalyzed strategy for the stereoselective synthesis of allylic amines that proceeds via an uncommon 1,2-hydrogen atom transfer (1,2-HAT) of nitrogen-centered radicals. This approach employs readily accessible hydroxamic acid derivatives as radical precursors. Through a rare intramolecular 1,2-HAT process, these substrates generate α-amino carbon-centered radicals, which are subsequently trapped by vinyl sulfones to afford the corresponding allylic amines in moderate to excellent yields with exclusive E-selectivity. The synthetic utility of this transformation was demonstrated by a scale-up reaction. This protocol features broad substrate scope and excellent functional group tolerance.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"18 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149152787","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
Enantioselective Copper-Catalyzed Addition-Elimination to Disulfonylethenes: Access to Unnatural α-quaternary Amino Acids Bearing Vinyl Sulfones 铜催化的对映选择性加成-消除对二磺乙烯：获取含乙烯基砜的非天然α-季氨基酸
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-14 DOI: 10.1039/d6qo01234e
Tian Cao,Xing Shang,Xihong Wang,Min Wang,Jian Liao
{"title":"Enantioselective Copper-Catalyzed Addition-Elimination to Disulfonylethenes: Access to Unnatural α-quaternary Amino Acids Bearing Vinyl Sulfones","authors":"Tian Cao,Xing Shang,Xihong Wang,Min Wang,Jian Liao","doi":"10.1039/d6qo01234e","DOIUrl":"https://doi.org/10.1039/d6qo01234e","url":null,"abstract":"Chiral vinyl sulfones represent versatile building blocks in organic synthesis and privileged structural motifs in medicinal chemistry, yet most existing methods afford racemic products. Herein, we report a copper-catalyzed asymmetric addition-elimination of aldimine esters with 1-aryl-1,2-bis(sulfonyl)ethenes, enabling rapid construction of chiral ɑ-quaternary amino acid derivatives bearing a vinyl sulfone moiety in good yields and excellent enantioselectivity. Synthetic utility is highlighted by late-stage natural product functionalization, scale-up experiment, versatile derivatizations, and concise synthesis of K777 analogue.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"187 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149152788","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
Supramolecular dimerization of thioxanthone for reactive oxygen species regulation in divergent aromatization and lactam formation 硫杂蒽酮的超分子二聚化对不同芳构化和内酰胺形成的活性氧调控
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-13 DOI: 10.1039/d6qo01337f
Rui-Ting Zhang,Yi-Ping Cao,Kai-Kai Niu,Wenli Ma,Ling-Bao Xing
{"title":"Supramolecular dimerization of thioxanthone for reactive oxygen species regulation in divergent aromatization and lactam formation","authors":"Rui-Ting Zhang,Yi-Ping Cao,Kai-Kai Niu,Wenli Ma,Ling-Bao Xing","doi":"10.1039/d6qo01337f","DOIUrl":"https://doi.org/10.1039/d6qo01337f","url":null,"abstract":"Selective activation of molecular oxygen is central to aerobic photocatalysis but remains difficult because competing oxygen-centered reactive species can lead to divergent reaction pathways. Here, we develop a supramolecular thioxanthone photocatalyst (TXPy-CB[8]) by organizing two pyridinium-functionalized TX units within cucurbit[8]uril in water. The confined host-guest assembly modulates the excited-state properties of TXPy and promotes electron-transfer activation of O2, leading predominantly to superoxide anion radicals (O2•‒) generation. TXPy-CB[8] enables efficient aerobic oxidative dehydrogenation of diverse tetrahydroquinolines, tetrahydroisoquinolines, indolines, hydrazobenzenes, and dihydropyridines to the corresponding aromatic products. Notably, the same photocatalytic platform enables divergent reactivity: tetrahydroquinoline affords quinoline under additive-free conditions, whereas addition of N,N-diisopropylethylamine (DIPEA) redirects the reaction toward dihydroquinolinone formation. Mechanistic and computational studies support O2•‒-mediated electron-transfer chemistry in both pathways and indicate that DIPEA alters the initial electron-transfer event, promoting subsequent peroxide-mediated oxygenation. Thus, supramolecular organization does not merely enhance reactive oxygen species (ROS) production but couples O2 activation to reaction-pathway selection, providing a strategy for divergent aerobic photocatalysis without changing the catalyst structure.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"232 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149152786","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
An introduction to modern reaction optimization in Python: how to develop and code a closed-loop reaction optimization system with Bayesian optimization, continuous-flow chemistry, and in-line analysis 介绍Python中的现代反应优化：如何使用贝叶斯优化、连续流化学和在线分析开发和编码闭环反应优化系统
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-13 DOI: 10.1039/d6qo01040g
Thibaud Mabit,Vanessa Kairouz,André B. Charette
{"title":"An introduction to modern reaction optimization in Python: how to develop and code a closed-loop reaction optimization system with Bayesian optimization, continuous-flow chemistry, and in-line analysis","authors":"Thibaud Mabit,Vanessa Kairouz,André B. Charette","doi":"10.1039/d6qo01040g","DOIUrl":"https://doi.org/10.1039/d6qo01040g","url":null,"abstract":"The digital transformation of chemical sciences is redefining how reaction optimization is implemented. This article provides a step-by-step guide to closed-loop optimization of organic reactions using Python, Bayesian optimization, continuous-flow chemistry, and in-line spectroscopic analysis. A nucleophilic aromatic substitution case study illustrates how computational tools and experimental chemistry can be integrated for efficient exploration of chemical space and rapid identification of optimal conditions. Key concepts are introduced and fully illustrated in the SI, with Jupyter Notebooks offering both complete code implementations and partially filled exercises for training. It is assumed that the reader has fundamental knowledge of Python, including conditionals, loops, coding structures as functions, and basic libraries. By bridging coding and practical experimental knowledge, this work highlights Python literacy as a central requirement for the next generation of chemists.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"232 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149152799","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
Vinylene carbonate as the carbon-heteroatom synthons via skeletal editing of free anilines to construct N-Arylation 2-Oxazolidinones † 碳酸乙烯作为碳杂原子合子，通过游离苯胺的骨架编辑构建n-芳基化2-恶唑烷酮†
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-13 DOI: 10.1039/d6qo01072e
Shijun Hong,Zhongwen Sun,Ruilin Zhang,Qing-Sheng Zhao,Tong Wang,Qianyao Zhang,Wenxin Huang
{"title":"Vinylene carbonate as the carbon-heteroatom synthons via skeletal editing of free anilines to construct N-Arylation 2-Oxazolidinones †","authors":"Shijun Hong,Zhongwen Sun,Ruilin Zhang,Qing-Sheng Zhao,Tong Wang,Qianyao Zhang,Wenxin Huang","doi":"10.1039/d6qo01072e","DOIUrl":"https://doi.org/10.1039/d6qo01072e","url":null,"abstract":"Skeletal editing is a highly efficient strategy for modifying the core scaffolds of drug molecules, with single-atomic editing as an emergent approach. Herein, we present a protocol for constructing N-arylation 2-oxazolidinones via vinylene carbonate, which provides four carbon-heteroatom sources through fouratom editing to modify free aniline building blocks via a Rh(III)catalyzed [4+1] annulation reaction. Remarkably, in this reaction, vinylene carbonate eliminates only one oxygen rather than CO2. This reaction integrates sequential olefin coordination/migratory insertion/protonation/nucleophilic addition/ring-opening/ringclosing in the continuous one-pot synthesis. This protocol exhibits excellent functional group tolerance, high atom economy and step economy, a broad substrate scope, and scalability for gram-scale synthesis, showcasing its applicability to drug molecules and highlighting its utility in organic synthesis and pharmaceutical chemistry. In addition, control experiments were conducted to elucidate the plausible reaction mechanism.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"1 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149152785","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
Catalytic formation of vinylic isonitriles via a nucleophilic isocyanation and olefin isomerization sequence 通过亲核异氰化和烯烃异构化序列催化形成乙烯基异硝基
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-13 DOI: 10.1039/d6qo00256k
Taiga Yurino,Ryota Saeki,Asuka Hachiya,Takeshi Ohkuma
{"title":"Catalytic formation of vinylic isonitriles via a nucleophilic isocyanation and olefin isomerization sequence","authors":"Taiga Yurino,Ryota Saeki,Asuka Hachiya,Takeshi Ohkuma","doi":"10.1039/d6qo00256k","DOIUrl":"https://doi.org/10.1039/d6qo00256k","url":null,"abstract":"A sequential method for the synthesis of vinylic isonitriles was developed, consisting of (1) Pd-catalyzed γ-selective isocyanation of allylic phosphates and (2) olefin isomerization of the resulting allylic isonitriles to the vinylic products. The design of the substrate was crucial for achieving successful conversion. An electron-withdrawing ester group placed at the α position to the leaving phosphate induced γ-selective substitution, while introduction of an aryl group at the γ position stabilized the vinylic isonitrile structure. The vinyli isonitriles thus obtained were converted into 2,4-disubstituted pyrroles in high yield via AgTFA-catalyzed cyclization with NaH as base. Finally, these catalytic isocyanation and cyclization sequences were successfully applied as the key steps in the formal total synthesis of vonoprazan.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"1 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149151943","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
Cu–NHC catalysis for radical ring-opening chalcogenation of gem-difluorocyclopropanes Cu-NHC催化宝石-二氟环丙烷自由基开环硫代反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-12 DOI: 10.1039/d6qo01202g
Shi-Jiao Zhang,Yu Teng,Meng-Qiang Cai,Hong-Shuang Li
{"title":"Cu–NHC catalysis for radical ring-opening chalcogenation of gem-difluorocyclopropanes","authors":"Shi-Jiao Zhang,Yu Teng,Meng-Qiang Cai,Hong-Shuang Li","doi":"10.1039/d6qo01202g","DOIUrl":"https://doi.org/10.1039/d6qo01202g","url":null,"abstract":"Conventional approaches for achieving ring-opening functionalization of gem-difluorocyclopropanes (gem-F2CPs) predominantly rely on precious metal catalysts such as palladium and rhodium. Herein, we report a radical ring-opening defluorinative chalcogenation of gem-F2CPs with Ebselen and its derivatives (e.g., benzoselenazolones, benzoisothiazolones) as radicalophiles, enabled by cost-effective and readily available copper(I) and N-heterocyclic carbene (NHC) catalysts. Employing PhSiH3 as the reductant, this synergistic catalytic system accommodates a broad range of substrates bearing diverse functionalities, providing regio- and stereoselective access to structurally distinct amide-tethered 2-fluoroallylic chalcogenides. Notably, late-stage diversification of natural products and approved pharmaceuticals further underscores the synthetic potential of this transformation. Mechanistic experiments indicate that the 2-fluoroallylic radical, generated through metal-catalyzed hydrogen atom transfer (MHAT) followed by β-F elimination, might be involved as the key intermediate in the Cu(II)–Cu(I) catalytic cycle.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"46 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149151939","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
Correction: Dendron-mediated control over self-assembly of chlorophyll rosettes into columnar discrete aggregates 校正：树突介导的叶绿素莲座自组装成柱状离散聚集体的控制
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-12 DOI: 10.1039/d6qo90073a
Ryo Kudo,Hiroki Hanayama,Balaraman Vedhanarayanan,Hitoshi Tamiaki,Nobuyuki Hara,Sarah E. Rogers,Martin J. Hollamby,Biplab Manna,Koji Harano,Shiki Yagai
{"title":"Correction: Dendron-mediated control over self-assembly of chlorophyll rosettes into columnar discrete aggregates","authors":"Ryo Kudo,Hiroki Hanayama,Balaraman Vedhanarayanan,Hitoshi Tamiaki,Nobuyuki Hara,Sarah E. Rogers,Martin J. Hollamby,Biplab Manna,Koji Harano,Shiki Yagai","doi":"10.1039/d6qo90073a","DOIUrl":"https://doi.org/10.1039/d6qo90073a","url":null,"abstract":"Correction for ‘Dendron-mediated control over self-assembly of chlorophyll rosettes into columnar vs. discrete aggregates’ by Ryo Kudo et al., Org. Chem. Front., 2024, 11, 6304–6310, https://doi.org/10.1039/d4qo01629g.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"47 41 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149151945","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
Orthogonally Protected Amino Acid Imides via CBr 4 Catalysed Visible Light Activation of Halogen Bonded EDA Complex 正交保护氨基酸亚胺通过cbr4催化卤素键合EDA配合物的可见光活化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-12 DOI: 10.1039/d6qo01357k
BINDUJA KADAMANNIL,Sunandan Sarkar,Baby Viswambharan
{"title":"Orthogonally Protected Amino Acid Imides via CBr 4 Catalysed Visible Light Activation of Halogen Bonded EDA Complex","authors":"BINDUJA KADAMANNIL,Sunandan Sarkar,Baby Viswambharan","doi":"10.1039/d6qo01357k","DOIUrl":"https://doi.org/10.1039/d6qo01357k","url":null,"abstract":"The unique synergy between halogen bonded electron donor-acceptor (EDA) complex and photo-activation that forges selective oxidative sp 3 C-H imidation of amino acids and peptides under metal-free, sustainable, and operationally simple aerobic condition is reported. Spectroscopic and DFT studies revealed the establishment of halogen bond between the N-acyl amino acid ester and CBr₄. Control experiments confirm the light promoted oxygen sensitization, generating radical intermediates responsible for the oxidative transformation in presence of benzoic acid. This halogen bonded photoactivation approach not only broadens the scope to late-stage photochemical C-H functionalization but also highlights the growing role of noncovalent interactions in efficient synthetic transformations.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"92 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149151940","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
Copper-catalyzed highly selective Ullmann-type indole-α--glycosylation 铜催化高选择性ullmann型吲哚-α-糖基化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-10-12 DOI: 10.1039/d6qo01221c
Junrui Wang,Jie Lv,Zhibin Huang,Yingsheng Zhao
{"title":"Copper-catalyzed highly selective Ullmann-type indole-α--glycosylation","authors":"Junrui Wang,Jie Lv,Zhibin Huang,Yingsheng Zhao","doi":"10.1039/d6qo01221c","DOIUrl":"https://doi.org/10.1039/d6qo01221c","url":null,"abstract":"Conventional approaches for the N-glycosylation of indoles typically depend on multi-step synthesis or Mitsunobu reactions and are limited by tedious procedures and poor stereocontrol. This study reports an efficient copper-catalyzed N-glycosylation using inexpensive, readily available glycosyl chlorides as donors for the selective N-glycosylation of indoles and various N-heterocycles. This approach exhibits a broad substrate scope and excellent stereoselectivity and is extendable to amines, amino acids, and complex bioactive molecules, broadening the scope of Ullmann coupling and offering a simple, practical route for efficient and selective synthesis of indole N-glycosides.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"23 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149151946","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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