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Cu-Catalyzed Cyanoalkyl-Alkynylation of gem-Disubstituted Alkenes to Construct All-Carbon Quaternary Center 铜催化宝石二取代烯烃的氰基烷基烷基化构造全碳季中心
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-11 DOI: 10.1039/d5qo01138h
Yuhang Luo, Xiangxiang Li, Xinjie Zhao, Baomin Yang, Yubo Wei, Guiping Qin
{"title":"Cu-Catalyzed Cyanoalkyl-Alkynylation of gem-Disubstituted Alkenes to Construct All-Carbon Quaternary Center","authors":"Yuhang Luo, Xiangxiang Li, Xinjie Zhao, Baomin Yang, Yubo Wei, Guiping Qin","doi":"10.1039/d5qo01138h","DOIUrl":"https://doi.org/10.1039/d5qo01138h","url":null,"abstract":"A copper-catalyzed cyanoalkyl-alkynylation of gem-disubstituted alkenes for the construction of the alkynyl all-carbon quaternary center is reported herein. This protocol enables the efficient synthesis of various cyano compounds with an alkynyl all-carbon quaternary center in good yields and overcomes the challenges posed by large steric hindrance and unstable alkylmetal species through using pyridine as a directing group. Preliminary mechanism studies indicated that a radical pathway might potentially be involved in this reaction.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"35 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145035571","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
1,6-Hydrosulfonylation of p-Quinone Methides Enabled via Strain-Release-/Aromaticity-Driven Alkyl Radical Generation and SO2-Capture: Synthesis and Antiproliferative Studies of Sulfonylated Diarylmethanes 通过释放/芳香驱动的烷基自由基生成和so2捕获实现对醌类化合物的1,6-氢磺化：磺化二芳基甲烷的合成和抗增殖研究
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-10 DOI: 10.1039/d5qo00981b
Dipun Kumar Penthi, Tonish Kumar Sahu, Rahimuddin Khan, Shanti Gopal Patra, Tabrez Khan
{"title":"1,6-Hydrosulfonylation of p-Quinone Methides Enabled via Strain-Release-/Aromaticity-Driven Alkyl Radical Generation and SO2-Capture: Synthesis and Antiproliferative Studies of Sulfonylated Diarylmethanes","authors":"Dipun Kumar Penthi, Tonish Kumar Sahu, Rahimuddin Khan, Shanti Gopal Patra, Tabrez Khan","doi":"10.1039/d5qo00981b","DOIUrl":"https://doi.org/10.1039/d5qo00981b","url":null,"abstract":"The integration of γ-keto sulfones, despite being a medicinally relevant building block with the bioactive diarylmethane motif, remains elusive. On the other hand, the fixation of SO2 in organic molecules for accessing value-added products is gaining wide attention in organic synthesis. Herein, we disclose the 1,6-hydrosulfonylation of p-quinomethides via the strain-release driven ring-scission of strained 3°-cyclopropanols in the presence of a SO2-surrogate like K2S2O5 and a Bronsted acid under visible-light photoredox catalysis to access a library of γ-keto alkylsulfonylated diarylmethanes in moderate to good yields. Also, the 1,6-hydrosulfonylation of p-quinone methides is developed via the aromaticity-driven bond-scission in pro-aromatics like 4-alkyl-1,4-DHPs in the presence of K2S2O5 and a Bronsted acid under visible-light photoredox catalysis to access a library of alkylsulfonylated diarylmethanes. The efficiency of the developed reactions has been established through broad substrate-scope studies, and the mechanistic probing studies have been complemented with DFT calculations to support the proposed mechanisms. In addition, antiproliferative studies revealed oral cancer activity for some of the synthesized sulfonylated diarylmethane derivatives.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"53 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145025278","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
AgOTf-Promoted Transetherification of p-Methoxybenzyl Ethers with Allyl and Benzyl Bromides agotf促进对甲氧基苄基醚与烯丙基和苄基溴醚的转醚化反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-09 DOI: 10.1039/d5qo00945f
Yufan Yang, Dongyang Jiang, Xuan Li, Juxi Wang, Lu Gao, Wanshu Wang, Zhenlei Song
{"title":"AgOTf-Promoted Transetherification of p-Methoxybenzyl Ethers with Allyl and Benzyl Bromides","authors":"Yufan Yang, Dongyang Jiang, Xuan Li, Juxi Wang, Lu Gao, Wanshu Wang, Zhenlei Song","doi":"10.1039/d5qo00945f","DOIUrl":"https://doi.org/10.1039/d5qo00945f","url":null,"abstract":"Conventional transetherification involves activation of the ether C-O bond, enabling either C-O/O-H bond metathesis with alcohols or C-O/C-O metathesis with other ethers. Here, we report an alternative approach based on an unusual C-O/C-Br bond metathesis. Silver triflate (AgOTf) promotes the transetherification of p-methoxybenzyl ethers (PMB-OR2 ) with allyl or benzyl bromides (R 1 -Br), selectively affording unsymmetrical ethers (R 1 -O-R 2 ). The reaction tolerates a wide range of functional groups that are incompatible with the strong bases required for Williamson ether synthesis. Furthermore, the method enables a three-component process involving R¹-Br, R²-Br, and PMBOH, where PMBOH acts as an \"oxygen linker\" through a sequential etherification/transetherification process. Mechanistic studies indicate a cationic pathway proceeding via a trialkyl oxonium intermediate.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"14 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145017826","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 water activation for the oxidative cleavage of alkenes 烯烃氧化裂解的电化学水活化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-09 DOI: 10.1039/d5qo00944h
Ning Zhang, Hui Zhou, Guojuan Liang, Gaochen Liu, Xing Liu, Pengfei Zhou, Dong Zhang, Jing Zhou
{"title":"Electrochemical water activation for the oxidative cleavage of alkenes","authors":"Ning Zhang, Hui Zhou, Guojuan Liang, Gaochen Liu, Xing Liu, Pengfei Zhou, Dong Zhang, Jing Zhou","doi":"10.1039/d5qo00944h","DOIUrl":"https://doi.org/10.1039/d5qo00944h","url":null,"abstract":"Oxidative cleavage of alkenes allows rapid access to valuable products, starting from simple petrochemicals. Water is an ideal carrier of oxygen. Here, we report a novel electrochemical water activation for the oxidative cleavage of alkenes. Water was used as an abundant and economical oxygen source, with no additional oxidants or complex workups. A wide range of alkenes such as activated alkenes and unactivated alkenes were tolerated. Additionally, we observed oxidative cleavage of the allylic C-C(vinyl) σ-bond and a unique linear paired electrolysis mode, which are not observed in existing methods for the oxidative cleavage of olefins.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"8 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145017825","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
Highly stereoselective synthesis of N-sulfonyl amidines with calcium carbide as an acetylene source 以电石为乙炔源合成n -磺酰脒的高立体选择性
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-09 DOI: 10.1039/d5qo01010a
Rui An, Weihao Cui, Peiming Gu, Meng-Xue Wei
{"title":"Highly stereoselective synthesis of N-sulfonyl amidines with calcium carbide as an acetylene source","authors":"Rui An, Weihao Cui, Peiming Gu, Meng-Xue Wei","doi":"10.1039/d5qo01010a","DOIUrl":"https://doi.org/10.1039/d5qo01010a","url":null,"abstract":"A practical and convenient approach for the highly stereoselective synthesis of <em>N</em>-sulfonyl amidines <em>via</em> a one-pot multi-component cascade reaction of sulfonyl azides, amines, water, and calcium carbide as an acetylene source has been developed, in which C–N and C<img alt=\"[double bond, length as m-dash]\" border=\"0\" src=\"https://www.rsc.org/images/entities/char_e001.gif\"/>N bonds are constructed simultaneously. The method exhibits a broad substrate scope (35 examples) with up to 93% yield and <em>E</em>/<em>Z</em> &gt; 99 : 1. Some deuterated products are readily prepared when deuterium water is used as a reagent. This protocol features mild reaction conditions, simple operation, and ready scalability.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"24 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145017824","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
Electrophilic insertion and ring growth in 1,2,5-azadiborolidines: theoretical evidence for boron-driven expansion 1,2,5-偶氮硼烷的亲电插入和环生长：硼驱动膨胀的理论证据
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-08 DOI: 10.1039/d5qo01081k
Victor A. Lucas-Rosales, Miguel A. Vázquez, Gabriel Merino, Albert Poater, J. Oscar C. Jiménez-Halla
{"title":"Electrophilic insertion and ring growth in 1,2,5-azadiborolidines: theoretical evidence for boron-driven expansion","authors":"Victor A. Lucas-Rosales, Miguel A. Vázquez, Gabriel Merino, Albert Poater, J. Oscar C. Jiménez-Halla","doi":"10.1039/d5qo01081k","DOIUrl":"https://doi.org/10.1039/d5qo01081k","url":null,"abstract":"This study computationally investigates the reactivity of 1,2,5-azadiborolidine derivatives toward carbon monoxide (CO), extending ring-expansion mechanisms from borole chemistry. Establishing structural and electronic analogies through isosterism, we propose that endocyclic CO insertion operates in this new class of boron heterocycles. 1,2,5-Tri-<em>tert</em>-butyl-1,2,5-azadiborolidine emerged as the optimal candidate, exhibiting a favourable three-step pathway: CO insertion, dimerization of the ring-expanded intermediate, and subsequent double [1,2]-migration. Thermochemical analysis confirms viability under mild conditions, with solvents (DCM, <em>n</em>-pentane, THF) providing similar barriers and reaction Gibbs energies. Key reactivity indicators include B–C(O) and C–O bond lengths, while correlations between kinetic barriers and σ → π*(CO) backdonation energies provide predictive insight. This work broadens boron-based reactivity by proposing a fourth class of CO-inserting boracycles and highlights 1,2,5-azadiborolidines as versatile, metal-free frameworks for small-molecule activation.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"24 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145009354","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
Site Selective Heck Arylation of N-Vinyl-7-Azaindole Engineered by N-Oxide Activation: Scope and Mechanistic Studies n -氧化活化工程n -乙烯基-7-叠氮树脂的位点选择性芳基化：范围和机制研究
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-05 DOI: 10.1039/d5qo00976f
Susanta Patra, Arunava Sengupta, Parthasarathi Das
{"title":"Site Selective Heck Arylation of N-Vinyl-7-Azaindole Engineered by N-Oxide Activation: Scope and Mechanistic Studies","authors":"Susanta Patra, Arunava Sengupta, Parthasarathi Das","doi":"10.1039/d5qo00976f","DOIUrl":"https://doi.org/10.1039/d5qo00976f","url":null,"abstract":"The palladium-catalyzed site-selective arylation of N-vinyl-7-azaindole (AI) derivatives using (hetero)iodoarenes is reported. While N-vinyl-7-azaindole displays moderate regioselectivity, predominantly favoring α-arylation, N-oxide activation (AINO) induces a complete switch to exclusive β-arylation with high E-selectivity. Control experiments and DFT studies support the mechanistic basis of this switch, which arises from the formation of distinct metallocyclic π-complexes: a five-membered complex for α-arylation and a six-membered complex for β-arylation. These findings highlight N-oxide activation as a powerful strategy to control regioselectivity in Heck-type arylations of N-vinyl-7-azaindoles. The transformation proceeds under ligand-free conditions and showcases broad substrate scope and excellent functional group tolerance.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"31 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145002973","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
Wavelength-tuned, photocatalytic chemoselective hydrodefluorination 波长调谐，光催化化学选择性加氢除氟
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-05 DOI: 10.1039/d5qo01012h
Meng Guo, Zhi-Peng Ye, Yong-Qing Ye, Xiao-Qing Chen, Kai Chen, Hua Yang
{"title":"Wavelength-tuned, photocatalytic chemoselective hydrodefluorination","authors":"Meng Guo, Zhi-Peng Ye, Yong-Qing Ye, Xiao-Qing Chen, Kai Chen, Hua Yang","doi":"10.1039/d5qo01012h","DOIUrl":"https://doi.org/10.1039/d5qo01012h","url":null,"abstract":"Selective hydrodefluorination of trifluoromethyl-bearing scaffolds remains challenging due to the unexpected over-defluorination. Herein, we report a photocatalytic chemoselective hydrodefluorination of trifluoromethyl acetamides enabled by readily tuning the wavelength of light irradiation, in which formate serves as both a hydrogen atom transfer (HAT) reagent and an electron donor for the EDA complex. This strategy enables the selective monohydrodefluorination and dihydrodefluorination of the trifluoromethyl unit under mild conditions, accommodating a variety of trifluoroacetamides. Mechanistic investigations disclosed that a wavelength-dependent SET/EDA manipulation is crucial to the chemoselectivity of this defluorination platform.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"15 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144995804","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
Streamlined synthesis of meta- or para-substituted triphenylamine[3]arenes and their hierarchical assembly into polyhedral cages 间或对取代三苯胺[3]芳烃的流线型合成及其在多面体笼中的分层组装
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-05 DOI: 10.1039/d5qo01089f
Wangjian Fang, Xin Li, Audrey Nathania, Yimin Zhang, Guoqiang Jiang, Andrew C.-H. Sue
{"title":"Streamlined synthesis of meta- or para-substituted triphenylamine[3]arenes and their hierarchical assembly into polyhedral cages","authors":"Wangjian Fang, Xin Li, Audrey Nathania, Yimin Zhang, Guoqiang Jiang, Andrew C.-H. Sue","doi":"10.1039/d5qo01089f","DOIUrl":"https://doi.org/10.1039/d5qo01089f","url":null,"abstract":"Triphenylamine[3]arenes (TPA[3]s) are a novel class of macrocyclic scaffolds with remarkable potential in supramolecular chemistry. In this study, we present a streamlined synthesis of TPA[3]s featuring meta or para-substituted bromophenyl or ester moieties on the nitrogen-bridging units via a BF3 •Et2O-catalysed one-pot Friedel-Crafts reaction, achieving up to nearquantitative yields within five minutes. These labile substituents at the equatorial positions enable efficient post-cyclisation functionalisation under mild conditions, facilitating the introduction of diverse functional groups, including nitrophenyl, pyrene, terpyridine, and carboxylic acid units. These meta-functionalised TPA[3]s exhibit exceptional structural flexibility, enabling their use as tri-topic building blocks for the construction of metal-organic cages (MOCs) through a subcomponent self-assembly strategy. By precisely tuning ligand denticity and metal coordination, we synthesised a diverse range of MOCs, including tetrahedral M4L4 cages, dimeric M3L2 assemblies, and octahedral M6L4 architectures. These results demonstrate the versatility of TPA[3] scaffolds in advancing hierarchical supramolecular assembly and highlight their potential for creating structurally diverse and well-defined supramolecular architectures.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"33 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144995653","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
Facile N-directed Ru-catalyzed C(3)-H acylation of heterocyclopentadienes with acyl chlorides 易氮定向钌催化的C(3)-H与酰基氯化物的酰化反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-05 DOI: 10.1039/d5qo00965k
Konstantin Shepelenko, Irina Gnatiuk, Andrey Aleksandrov, Mikhail Evgenevich Minyaev, Victor Chernyshev, Valentine P. Ananikov
{"title":"Facile N-directed Ru-catalyzed C(3)-H acylation of heterocyclopentadienes with acyl chlorides","authors":"Konstantin Shepelenko, Irina Gnatiuk, Andrey Aleksandrov, Mikhail Evgenevich Minyaev, Victor Chernyshev, Valentine P. Ananikov","doi":"10.1039/d5qo00965k","DOIUrl":"https://doi.org/10.1039/d5qo00965k","url":null,"abstract":"The selective C3‒H functionalization of 2-substituted heterocyclopentadienes (furan, thiophene and pyrrole) remains challenging owing to the typically higher reactivity of the C5‒H and C4‒H bonds. In this study, we report a facile method for the selective C3-H arylation of pharmaceutically and agrochemically relevant heterocyclopentadienes bearing N-donor directing groups at the 2-position. This approach utilizes readily available aliphatic, aromatic and heteroaromatic acyl chlorides under catalysis by a Ru/PPh₃ system generated in situ from commercially available, bench-stable precursors. The method exhibits broad tolerance toward various N-donor directing groups, including those with unprotected NH moieties potentially susceptible to N-acylation. Preliminary mechanistic studies suggest that a reaction pathway involving rate-limiting C-H activation assisted by the carboxylate anion generated via partial solvolysis of the acyl chloride.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"30 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144995652","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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