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Sc(OTf)3-Catalyzed Construction of Fused Bisindolylmethanes: Unified Access to 1,2- and 1,7-Linked Indole Frameworks. Sc(OTf)3催化合成融合双吲哚甲烷：1,2-和1,7-连接吲哚框架的统一获取。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-30 DOI: 10.1021/acs.orglett.5c03698
Peng Long,Kang Dong,Xiaomeng Gong,Ruipeng Li,Huiwen Yang,Weiwei Zhang,Shouchu Tang
{"title":"Sc(OTf)3-Catalyzed Construction of Fused Bisindolylmethanes: Unified Access to 1,2- and 1,7-Linked Indole Frameworks.","authors":"Peng Long,Kang Dong,Xiaomeng Gong,Ruipeng Li,Huiwen Yang,Weiwei Zhang,Shouchu Tang","doi":"10.1021/acs.orglett.5c03698","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03698","url":null,"abstract":"We report a concise, efficient, and scalable synthetic strategy for the construction of fused bisindolylmethanes (BIMs) via Sc(OTf)3-catalyzed Friedel-Crafts cyclization of N-alkyl acetal indoles. This protocol enables regioselective access to both 1,2- and previously unexplored 1,7-fused BIMs under mild and operationally simple conditions. The transformation demonstrates broad substrate tolerance and excellent functional group compatibility, delivering structurally diverse fused indole architectures with potential relevance in medicinal chemistry, complex molecule synthesis, and late-stage peptide modification.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"221 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145194612","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
Introducing N-Carboxyethyl-Ynamides, Precursors of Metalated Ketenimines: Protecting Group Swap in Ynamides and Olefination of Aldehydes. 介绍n -羧基乙基酰胺、金属化氯胺胺前体：酰胺中的保护基团交换和醛的烯烃化。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-30 DOI: 10.1021/acs.orglett.5c03692
Phidéline Gérard,Yohann Landrain,Thibault Heymans,Gwilherm Evano
{"title":"Introducing N-Carboxyethyl-Ynamides, Precursors of Metalated Ketenimines: Protecting Group Swap in Ynamides and Olefination of Aldehydes.","authors":"Phidéline Gérard,Yohann Landrain,Thibault Heymans,Gwilherm Evano","doi":"10.1021/acs.orglett.5c03692","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03692","url":null,"abstract":"N-Carboxyethyl-ynamides are shown to be useful and versatile precursors of metalated ketenimines. Upon simple treatment with a strong base, a retro-Michael addition indeed affords these highly reactive ambident electrophilic intermediates that can hardly be generated otherwise. Their reaction with chloroformates, acyl chlorides, chlorophosphates, and chlorosilanes regioselectively occurs at the nitrogen atom and provides a useful entry to novel ynamides possessing two electron-withdrawing groups on the nitrogen atom by an unprecedented protecting group swap. In sharp contrast, their condensation with aldehydes exclusively takes place on the distal carbon atom, resulting in an efficient and stereoselective olefination.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"99 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145194610","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 Direct Photolysis of Phosphorus Iodide Salts for Difluoroalkylation of C(sp2)-H by an Intramolecular Charge-Transfer Complex. 用分子内电荷转移配合物对C(sp2)-H的二氟烷基化进行可见光诱导的碘化磷盐直接光解。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-30 DOI: 10.1021/acs.orglett.5c03255
Jie Sun,Jintong Xie,Wen Lin,Jianjun Li
{"title":"Visible-Light-Induced Direct Photolysis of Phosphorus Iodide Salts for Difluoroalkylation of C(sp2)-H by an Intramolecular Charge-Transfer Complex.","authors":"Jie Sun,Jintong Xie,Wen Lin,Jianjun Li","doi":"10.1021/acs.orglett.5c03255","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03255","url":null,"abstract":"Green, safe, simple, and efficient strategies for generating fluoroalkyls are an ongoing challenge for the synthetic community. Generally, the main form of synthesizing difluoroalkylated heteroaromatic compounds is to use catalysts, oxidants, and a high temperature to generate difluoroalkyl radicals and react with heteroaromatic hydrocarbons. In contrast, the strategy of using intramolecular charge-transfer complexes (ICTCs) to generate difluoroalkylated heteroaromatic compounds remains an unexplored challenge. Here, for the first time, we carried out a difluoromethylation reaction between various difluoroalkyl radicals generated in the form of photoactivated ICTCs and heteroaromatic C(sp2)-H compounds (with high stability and multiple active sites) to obtain various fluorine-containing compounds. This method only depends on the substrate in the reaction, avoiding the need for a metal, exogenous photocatalyst, and oxidant. In addition, this metal-free approach provides controlled synthetic conditions, employs a scalable flow technique with high temporal and spatial efficiency, and demonstrates successful gram-scale applications, thus proving the usefulness and versatility of this new scheme.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"148 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145189236","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
Chemodivergent Synthesis of Multiborylalkanes via Deoxygenative Polyborylation of Silyl Enol Ethers. 硅烯醚脱氧多硼化反应合成多硼烷的化学发散性研究。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-30 DOI: 10.1021/acs.orglett.5c03751
Wenke Dong,Honghui Ma,Wanxiang Zhao
{"title":"Chemodivergent Synthesis of Multiborylalkanes via Deoxygenative Polyborylation of Silyl Enol Ethers.","authors":"Wenke Dong,Honghui Ma,Wanxiang Zhao","doi":"10.1021/acs.orglett.5c03751","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03751","url":null,"abstract":"A cobalt-catalyzed, chemodivergent deoxygenative polyborylation strategy for silyl enol ethers has been developed, enabling selective synthesis of 1,1,1-triborylalkanes, 1,1,3-triborylalkanes, 1,1-diborylalkenes, and 1,1-diborylalkanes. Specifically, deoxygenative borylation with B2pin2 affords 1,1,1-triborylalkanes, 1,1,3-triborylalkanes, and 1,1-diborylalkenes, while the use of HBpin favors 1,1-diborylalkane formation. This protocol offers mild reaction conditions, a broad substrate scope, and high functional group tolerance. The utility and practicality of this method were demonstrated through gram-scale reactions and various product transformations. Mechanistic investigations revealed that all processes are initiated via the cobalt-catalyzed dehydrogenative and deoxygenative borylation of silyl enol ethers.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"39 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145189233","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
Cobalt-Catalyzed Intramolecular Fluoroalkylative Carbonylation of Unactivated Alkenes. 钴催化非活化烯烃的分子内氟烷基羰基化。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-30 DOI: 10.1021/acs.orglett.5c03691
Donghao Jiang,Zhudi He,Wei Li,Li-Jie Cheng
{"title":"Cobalt-Catalyzed Intramolecular Fluoroalkylative Carbonylation of Unactivated Alkenes.","authors":"Donghao Jiang,Zhudi He,Wei Li,Li-Jie Cheng","doi":"10.1021/acs.orglett.5c03691","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03691","url":null,"abstract":"A cobalt-catalyzed intramolecular fluoroalkylative carbonylation of unactivated alkenes has been developed, enabling the highly regioselective synthesis of fluoroalkylated γ-lactones in good yields. The mild reaction conditions exhibit good functional group tolerance, and the reaction can be performed on a large scale. Preliminary mechanistic investigations support a radical pathway in which a cationic acylcobalt(IV) complex is proposed as the key intermediate.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"53 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145194609","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 Densely Functionalized Pyrroles via Photoinduced C-Insertion into N-Alkylenamines: Sequential C(sp2)-H/C(sp3)-H Activation with Bromine Radicals. 光诱导C插入n -烷基胺合成密集功能化吡咯：C(sp2)-H/C(sp3)-H与溴自由基的顺序活化。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-30 DOI: 10.1021/acs.orglett.5c03559
Chuan-Hua Qu,Su-Ya Liu,Shan-Shan Chen,Nian Wang,Ying Cheng,Shi-You Xue,Xue-Ying Yang,Wen-Bin Zong,Yuan Zhou,Li-Min Zhang,Xiang-Yi Zeng,Qin-Mao Li,Lan-Bin He,Xiao Yan,Gui-Ting Song
{"title":"Synthesis of Densely Functionalized Pyrroles via Photoinduced C-Insertion into N-Alkylenamines: Sequential C(sp2)-H/C(sp3)-H Activation with Bromine Radicals.","authors":"Chuan-Hua Qu,Su-Ya Liu,Shan-Shan Chen,Nian Wang,Ying Cheng,Shi-You Xue,Xue-Ying Yang,Wen-Bin Zong,Yuan Zhou,Li-Min Zhang,Xiang-Yi Zeng,Qin-Mao Li,Lan-Bin He,Xiao Yan,Gui-Ting Song","doi":"10.1021/acs.orglett.5c03559","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03559","url":null,"abstract":"Photoinduced Csp3-Br bond homolysis of ArCOCF2Br using triethylamine as the halogen bonding (XB) acceptor was a key step for the [2 + 2 + 1] cyclization. An unprecedented strategy for assembling privileged pyrroles and their fused scaffolds via metal-, oxidant-free C-incorporation into N-alkylenamines through a triple-cleavage process has been disclosed. This method uses readily available alkyl amines, alkynes, or CF3-containing N-benzylenamines as the starting material and features two consecutive C-C-forming reactions with ArCOCF2Br as the carbon source. The transformation exploits the dual reactivity of bromine radicals─hydrogen-atom transfer (HAT) and reversible radical addition (RRA)─to coactivate the N-alkylenamines, and the resulting open-shell intermediates are then intercepted by in situ-generated difluoroalkyl radicals to deliver the target heterocycles.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"31 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145194917","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
From Refrigerant to Reagent: Repurposing HFC-125 into Inorganic and Organic Fluorinating Agents. 从制冷剂到试剂：将HFC-125重新用于无机和有机氟化剂。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-29 DOI: 10.1021/acs.orglett.5c03605
Hiroto Iwasaki,Zhengyu Zhao,Syunsuke Nanya,Naoyuki Hoshiya,Yosuke Kishikawa,Norio Shibata
{"title":"From Refrigerant to Reagent: Repurposing HFC-125 into Inorganic and Organic Fluorinating Agents.","authors":"Hiroto Iwasaki,Zhengyu Zhao,Syunsuke Nanya,Naoyuki Hoshiya,Yosuke Kishikawa,Norio Shibata","doi":"10.1021/acs.orglett.5c03605","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03605","url":null,"abstract":"We report a sustainable and atom-economical strategy to repurpose the refrigerant HFC-125 (CF3CF2H) into two valuable fluorinating agents: potassium fluoride (KF) and 1,1,2,2-tetrafluoro-N,N-dimethylethylamine (TFEDMA). Treatment of HFC-125 with KHMDS in toluene at low temperature induces deprotonation and β-fluoride elimination, quantitatively generating KF. The resulting crude KF, designated as KF125, efficiently promotes a range of nucleophilic fluorination reactions. Simultaneously, the cogenerated tetrafluoroethylene (TFE) is converted into TFEDMA, achieving complete utilization of HFC-125. This dual-reagent platform represents a practical and scalable approach to upcycling fluorinated industrial feedstocks for synthetic applications.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"89 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145188828","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
Ion-Pairing Assemblies of Oxacorrole AgIII Complex. Oxacorrole AgIII配合物的离子配对组合。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-29 DOI: 10.1021/acs.orglett.5c03523
Rima Sengupta,Kohei Kawami,Yukihide Ishibashi,Tsuyoshi Asahi,Hiromitsu Maeda
{"title":"Ion-Pairing Assemblies of Oxacorrole AgIII Complex.","authors":"Rima Sengupta,Kohei Kawami,Yukihide Ishibashi,Tsuyoshi Asahi,Hiromitsu Maeda","doi":"10.1021/acs.orglett.5c03523","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03523","url":null,"abstract":"In this study, ion pairs of 10-oxacorrole AgIII complex as an aromatic [17]oxaannulene were synthesized, leveraging its small inner cavity. The cation formed solid-state ion-pairing assemblies whose packing structures were governed by the stacking of π-planes along with dipole-dipole, hydrogen-bonding, and C-H···π interactions, depending on the counteranions. The 10-oxacorrole AgIII complex deviated from planarity due to the insertion of a relatively large AgIII into the confined cavity. Theoretical studies of packing structures have revealed that ion-pairing assemblies can be constructed by combining electrostatic and dispersion forces controlled by the location and spatial arrangement of the constituent charged species.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"12 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145188830","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
Photoinduced Pd-Catalyzed Carbonylative Formal [2 + 2] Cycloaddition of Alkylarenes and Imines 光诱导pd催化烷基烯和亚胺羰基化形式[2 + 2]环加成
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-29 DOI: 10.1021/acs.orglett.5c03465
Yi-Cong Liu, Wen-Ao Li, Mostafa Sayed, Zhi-Yong Han, Liu-Zhu Gong
{"title":"Photoinduced Pd-Catalyzed Carbonylative Formal [2 + 2] Cycloaddition of Alkylarenes and Imines","authors":"Yi-Cong Liu, Wen-Ao Li, Mostafa Sayed, Zhi-Yong Han, Liu-Zhu Gong","doi":"10.1021/acs.orglett.5c03465","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03465","url":null,"abstract":"A photoinduced palladium-catalyzed carbonylative formal [2 + 2] cycloaddition of toluene derivatives and imines provides a direct access to β-lactams under mild conditions (35 °C, 455 nm LED, 2 bar CO) with up to 99% yields. This three-component reaction accommodates both aldimines and ketimines as well as diverse aryl substrates, including ethylbenzene derivatives. Mechanistic studies reveal a sequential process consisting of C–H bond activation, carbonylation, and in situ ketene formation. This atom-economical protocol offers a valuable synthetic route to pharmaceutically important β-lactam scaffolds directly from readily available starting materials.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"29 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145183065","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 Domino Bis-[3 + 2]-Annulation of Ethynyl Cyclic Carbonates with Trifluoromethyl Azlactones. 铜催化的多米诺双-[3 + 2]-环碳酸乙酯与三氟甲基阿兹内酯的环化。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-29 DOI: 10.1021/acs.orglett.5c03716
Chada Raji Reddy,Sana Fatima,Nagender Punna,Balasubramanian Sridhar
{"title":"Copper-Catalyzed Domino Bis-[3 + 2]-Annulation of Ethynyl Cyclic Carbonates with Trifluoromethyl Azlactones.","authors":"Chada Raji Reddy,Sana Fatima,Nagender Punna,Balasubramanian Sridhar","doi":"10.1021/acs.orglett.5c03716","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03716","url":null,"abstract":"Herein, we introduce a novel bis-annulation of ethynyl cyclic carbonates with trifluoromethyl azlactones, enabling the assembly of a pyrrolidine-fused lactone containing two quaternary-bridged stereocenters. The reaction proceeds through two [3 + 2]-annulations in a domino mode involving decarboxylative propargylation/lactone formation/aza-annulation reactions with high diastereoselectivity. Interestingly, the scope was extended to ethynyl cyclic carbamates to construct pyrrolidine-fused lactams. This protocol reveals the utility of three reactive sites of both precursors in a single operation for the first time. Further, the scale-up and diverse transformations of the product highlighted its synthetic utility.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"68 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145188854","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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