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Facile One-pot Carboxylation and Ethoxycarbonylation of Aryl Halides and Thianthrenium Salts Using Difluorocarbene as CO Surrogate
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-11-10 DOI: 10.1039/d6qo01335j
Yan Li,Wenfei Hu,Tianbo Wang,Wai Chung Fu
{"title":"Facile One-pot Carboxylation and Ethoxycarbonylation of Aryl Halides and Thianthrenium Salts Using Difluorocarbene as CO Surrogate","authors":"Yan Li,Wenfei Hu,Tianbo Wang,Wai Chung Fu","doi":"10.1039/d6qo01335j","DOIUrl":"https://doi.org/10.1039/d6qo01335j","url":null,"abstract":"Straightforward and operationally simple Pd-catalyzed methods are developed for facile ethoxycarbonylation and one-pot carboxylation of aryl bromides. Easily available catalysts are used and cost-efficient BrCF2COOEt is employed as CO surrogate via the in situ hydrolysis of [PdII]=CF2 species. Our strategy provides a broad scope of aryl esters and carboxylic acids with ample functional group tolerance. Notably, aryl thianthrenium triflates are applicable substrates and a one-pot three-step synthesis is devised to chemoselectively carboxylate arene C-H bonds.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"16 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149374980","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
Electrochemical Ritter-Type Selenylation-Amination of -Difluoroalkenes
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-11-10 DOI: 10.1039/d6qo01413e
Kaihui Zhong,Jiawei Huang,Xin-Yue Fang,Zihong Liu,Mu Chen,Zhixiong Ruan,Xinwei Hu
{"title":"Electrochemical Ritter-Type Selenylation-Amination of -Difluoroalkenes","authors":"Kaihui Zhong,Jiawei Huang,Xin-Yue Fang,Zihong Liu,Mu Chen,Zhixiong Ruan,Xinwei Hu","doi":"10.1039/d6qo01413e","DOIUrl":"https://doi.org/10.1039/d6qo01413e","url":null,"abstract":"Herein, an electrochemical Ritter-type three-component tandem reaction has been developed to achieve the selenylationamination or selenylation-azolation difunctionalization of gem-difluoroalkenes. This synthetic system is compatible with numerous nitrogen-heterocyclic derivatives, enabling the facile and efficient construction of diverse fluorinated organic skeletons. The method features broad substrate tolerance and mild reaction conditions, and can be readily scaled up to gram-scale preparation. It offers an efficient and feasible synthetic strategy for the electrochemical C-Se/C-N dual functionalization of gem-difluoroalkenes.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"37 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149374940","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
Visible-Light-Induced Four-Component Radical Cascade for the Synthesis of α-Alkylsulfonyl Ketoximes
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-11-10 DOI: 10.1039/d6qo01415a
Wei Li,Tianfeng Cui,Huiquan Ji,Guoao Wang,Wen-Bo Zhang,Dong-Liang Mo,Lin He,Qing-Qing Liu,Huaifeng Li
{"title":"Visible-Light-Induced Four-Component Radical Cascade for the Synthesis of α-Alkylsulfonyl Ketoximes","authors":"Wei Li,Tianfeng Cui,Huiquan Ji,Guoao Wang,Wen-Bo Zhang,Dong-Liang Mo,Lin He,Qing-Qing Liu,Huaifeng Li","doi":"10.1039/d6qo01415a","DOIUrl":"https://doi.org/10.1039/d6qo01415a","url":null,"abstract":"α-Sulfonyl ketoximes are privileged scaffolds in drug design. Although α-arylsulfonyl ketoximes are well established synthetically, efficient methods for accessing α-alkylsulfonyl ketoximes remain underdeveloped. Herein, we report the first photocatalytic four-component radical cascade for the synthesis of α-alkylsulfonyl ketoximes from alkyl carboxylic acids, DABSO, alkenes, and tert-butyl nitrite. This method overcomes the limitations of existing approaches that require presynthesized alkylsulfonylating reagents, providing a direct and modular route to α-alkylsulfonyl ketoximes, offering advantages such as readily available starting materials without preactivation, broad substrate scope, and enabling gramscale synthesis and downstream derivatization. Preliminary mechanistic studies indicate that the key to the success of this reaction lies in the decarboxylation of the acridine-carboxylic acid complex via light-induced proton-coupled electron transfer (PCET), as well as the dual role of tert-butyl nitrite as an endogenous oxidant and a source of NO radicals following photolysis.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"19 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149374942","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
Modular Synthesis of δ-Keto Esters via Synergistic Photoredox/NHC-Catalyzed Three-Component 1,2-Alkylacylation of Alkenes
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-11-10 DOI: 10.1039/d6qo01148a
Wen-Lin Zou,Zhi Guan,Yan-Hong He
{"title":"Modular Synthesis of δ-Keto Esters via Synergistic Photoredox/NHC-Catalyzed Three-Component 1,2-Alkylacylation of Alkenes","authors":"Wen-Lin Zou,Zhi Guan,Yan-Hong He","doi":"10.1039/d6qo01148a","DOIUrl":"https://doi.org/10.1039/d6qo01148a","url":null,"abstract":"A general and mild strategy for the synthesis of δ‑keto esters via multicomponent 1,2-alkylacylation of alkenes has been developed using synergistic photoredox and N-heterocyclic carbene (NHC) dual catalysis. This transformation features high step economy, and is amenable to gram-scale synthesis, enabling the efficient and modular assembly of a range of styrenes, malonates, and acyl imidazoles. Collectively, this work provides a rapid and efficient route to structurally diverse δ‑keto esters.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"20 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149374944","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
Stoichiometric plasticity in supramolecular host-guest systems: insights from indicator displacement assays
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-11-10 DOI: 10.1039/d6qo01428c
Alba Pereira-Vilar,Angel Acuña,Manuel Martin-Pastor,Nuno Basilio,Belen Vaz,Moisés Pérez-Lorenzo,Luis Garcia Rio
{"title":"Stoichiometric plasticity in supramolecular host-guest systems: insights from indicator displacement assays","authors":"Alba Pereira-Vilar,Angel Acuña,Manuel Martin-Pastor,Nuno Basilio,Belen Vaz,Moisés Pérez-Lorenzo,Luis Garcia Rio","doi":"10.1039/d6qo01428c","DOIUrl":"https://doi.org/10.1039/d6qo01428c","url":null,"abstract":"Indicator Displacement Assays (IDAs) have long represented a cornerstone in supramolecular sensing, relying on the competitive exchange between an indicator dye and an analyte for access to a host cavity, with the analytical response typically arising upon release of the reporter. Here, a multicomponent host-guest system is shown to display a high degree of stoichiometric plasticity, with its supramolecular organization adapting to changes in composition beyond the classical binary host-indicator-analyte picture. This plasticity leads to the redistribution of supramolecular species and to a nonmonotonic response that cannot be accounted for by a simple competitive exchange model. Fluorescence and NMR spectroscopy, combined with quantitative equilibrium modelling, reveal the underlying reorganization and establish its relationship with the observed response. The results demonstrate that stoichiometric plasticity can profoundly influence the macroscopic properties of multicomponent supramolecular systems, extending the mechanistic picture of indicator displacement assays beyond simple binary competition. More broadly, this work highlights the importance of considering adaptable host-guest organization when describing complex supramolecular systems and illustrates how indicator displacement assays can provide insights into their underlying binding equilibria.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"23 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149374943","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
Direct access to sulfonimidoyl chlorides from aryl thiols an -chloro--fluoroarenesulfonamide-mediated cascade of oxidation, chlorination, and imidation 从芳基硫醇和-氯氟磺酰胺介导的级联氧化、氯化和酰化直接获得磺酰酰氯
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-11-09 DOI: 10.1039/d6qo01240j
Yi Xi,Xuan-Kai Chen,Zhi-Qiang Wang,Xian-Jin Yang
{"title":"Direct access to sulfonimidoyl chlorides from aryl thiols an -chloro--fluoroarenesulfonamide-mediated cascade of oxidation, chlorination, and imidation","authors":"Yi Xi,Xuan-Kai Chen,Zhi-Qiang Wang,Xian-Jin Yang","doi":"10.1039/d6qo01240j","DOIUrl":"https://doi.org/10.1039/d6qo01240j","url":null,"abstract":"A direct synthesis of sulfonimidoyl chlorides from aryl thiols has been developed under mild conditions through an N-chloro-N-fluoroarenesulfonamide-mediated cascade of oxidation, chlorination, and imidation. The transformation proceeds to completion within 1 s, and the subsequent addition of TBAF enables one-pot conversion of the sulfonimidoyl chlorides into the corresponding sulfonimidoyl fluorides within seconds.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"9 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149368242","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
Iron-Catalyzed Regioselective 1,2-Alkylboration of Alkenes and Alkynes 铁催化烯烃和炔烃的区域选择性1,2-烷基化反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-11-07 DOI: 10.1039/d6qo01378c
Rahul S Amberkhed,Subramaniyan Ramkumar,Ganesh Kisan Dhole,Sakar Mohan,Srinivasa Budagumpi,Shubhankar Kumar Bose
{"title":"Iron-Catalyzed Regioselective 1,2-Alkylboration of Alkenes and Alkynes","authors":"Rahul S Amberkhed,Subramaniyan Ramkumar,Ganesh Kisan Dhole,Sakar Mohan,Srinivasa Budagumpi,Shubhankar Kumar Bose","doi":"10.1039/d6qo01378c","DOIUrl":"https://doi.org/10.1039/d6qo01378c","url":null,"abstract":"Non-precious metal-catalyzed difunctionalization of readily available alkenes and alkynes has emerged as one of the most straightforward and powerful strategies for the synthesis of functionalized organoboron compounds. Herein, we report the first heterogeneous iron-catalyzed three-component synthesis of multi-substituted alkyl- and alkenyl-boronates from the cross-coupling of bis(pinacolato)diboron (B2pin2) and an alkyl halide electrophile with an alkene or alkyne. A wide range of alkenes and alkynes readily undergo coupling with various alkyl halides, affording the desired products with excellent functional-group tolerance. Mechanistic investigations support a non-radical reaction pathway. Catalyst recyclability, synthetic transformations, and gram-scale reaction further highlight the practical usefulness of the method.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"29 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149360257","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
In-Situ Generation of Cyanomethyl Anions Driven by Electrical Pulses for the Synthesis of β-Hydroxy/Ketone Nitriles 电脉冲驱动氰基阴离子原位生成用于合成β-羟基/酮腈
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-11-07 DOI: 10.1039/d6qo01236a
Zhizi Wang,Jintong Xie,Chenxi Gu,Yali He,Jie Sun,Jiadi Zhou,Jianjun Li
{"title":"In-Situ Generation of Cyanomethyl Anions Driven by Electrical Pulses for the Synthesis of β-Hydroxy/Ketone Nitriles","authors":"Zhizi Wang,Jintong Xie,Chenxi Gu,Yali He,Jie Sun,Jiadi Zhou,Jianjun Li","doi":"10.1039/d6qo01236a","DOIUrl":"https://doi.org/10.1039/d6qo01236a","url":null,"abstract":"Here, We report an electrochemical protocol for the synthesis of β‑hydroxy/ketonitriles, which relies on the in situ generation of cyanomethyl anions under pulsed electrical conditions. This method obviates the requirement for a divided cell, low‑temperature operations, and metal additives. In addition, we have systematically investigated the distinct influences of stirring and substituent effects on the reaction selectivity, and have established a set of general principles that govern the observed product distribution.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"110 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149360256","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
Triplet free carbene-initiated formal semipinacol rearrangement and cyclopropanation via energy transfer photocatalysis 能量转移光催化下三态游离碳引发的正规半品萘酚重排和环丙化反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-11-06 DOI: 10.1039/d6qo01438k
Xuliang Duan,Xi Chen,Ziyi Li,Abdulla Yusuf,Guohua Miao,Shanlaing Dong,Zhuofeng Ke,Xinfang Xu
{"title":"Triplet free carbene-initiated formal semipinacol rearrangement and cyclopropanation via energy transfer photocatalysis","authors":"Xuliang Duan,Xi Chen,Ziyi Li,Abdulla Yusuf,Guohua Miao,Shanlaing Dong,Zhuofeng Ke,Xinfang Xu","doi":"10.1039/d6qo01438k","DOIUrl":"https://doi.org/10.1039/d6qo01438k","url":null,"abstract":"In spite of the dramatic surge in visible-light-mediated free carbene transfer reactions of diazo compounds, the catalytic generation and transformation of triplet carbene species remain a formidable challenge due to the stepwise pathways, which involve highly reactive diradical intermediates whose reactivity is difficult to predictable. Herein, we report a visible-light-induced formal semipinacol rearrangement of allylic alcohols with triplet carbenes derived from diazoacetates through energy transfer photocatalysis under mild and redox neutral conditions. In this reaction, allylic alcohols serve as triplet carbene acceptors, which accept a single electron through addition to the π-bond at an early stage, and subsequently terminate the remaining carbon-centered radical via a hydrogen atom transfer (HAT) process with the tethered hydroxyl group at a later stage, accompanied by a synchronous Neophyl-type rearrangement. The resulting functionalized linear ketone products can be readily converted into structurally diverse heterocycles through downstream transformations. This energy transfer photocatalysis protocol for generating triplet carbene species is also effective for the stepwise cyclopropanation of various alkenes.Notably, electron-deficient olefins and pyridinyl-substituted diazo compounds are compatible with this photocatalytic [2+1]-cycloaddition, delivering cyclopropanes in synthetically useful yields. This method represents a fundamentally distinct and complementary strategy to established carbene transfer reactions via metal-catalysis or direct photolysis.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"110 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149360293","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
Syntheses and transformations of N-allenyl and N-prop-1-ynyl sulfoximines n -烯基和n -丙-1-炔基亚砜亚胺的合成与转化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2026-11-06 DOI: 10.1039/d6qo01060a
Benjamin J. Statham,Pola Hild,Kari Rissanen,Carsten Bolm
{"title":"Syntheses and transformations of N-allenyl and N-prop-1-ynyl sulfoximines","authors":"Benjamin J. Statham,Pola Hild,Kari Rissanen,Carsten Bolm","doi":"10.1039/d6qo01060a","DOIUrl":"https://doi.org/10.1039/d6qo01060a","url":null,"abstract":"In both academia and industry, interest in the sulfoximidoyl group has steadily increased over the years, driven by the prospect of applications in drug discovery and crop protection. Within the field, developing new N-functionalisations has remained an active research topic. In the current work, we prepared previously unreported N-allenyl and N-prop-1-ynyl sulfoximines. These molecules bear structural similarities to allenamines/ynamines and allenamides/ynamides, the latter being synthetically useful classes of compounds. A successful strategy for the preparation of the N-allenyl and N-prop-1-ynyl sulfoximines is disclosed, and some synthetic applications of the compounds are described.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"13 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149360258","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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