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Steric Gating of Excited-State Channel: Controllable AIE/RTP Switching through Tuning π-Bond Twisting. 激发态通道的空间门控：通过调节π键扭转来控制AIE/RTP切换。
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-06-13 Epub Date: 2025-06-03 DOI: 10.1021/acs.orglett.5c01691
Hongli Xue, Changqing Ye, Haiyang Huang, Hongli Bao
{"title":"Steric Gating of Excited-State Channel: Controllable AIE/RTP Switching through Tuning π-Bond Twisting.","authors":"Hongli Xue, Changqing Ye, Haiyang Huang, Hongli Bao","doi":"10.1021/acs.orglett.5c01691","DOIUrl":"10.1021/acs.orglett.5c01691","url":null,"abstract":"<p><p>We demonstrate steric control of excited-state channel in π-conjugated 1,1'-bibenzo[<i>f</i>]isoindolylidenes through substituent-engineered C═C bond twisting. By tuning substituent bulkiness (R<sup>2</sup>), we achieve dynamic switching between aggregation-induced emission and dilute/dual-state fluorescence. The mechanical gating of biradicaloid isomerization channels was confirmed by variable-temperature NMR and EPR spectroscopy. The π-twisting activates low-energy CI pathways for AIE generation, while excessive bulkiness relocks molecular conformation, enabling solution-phase emission. This steric gating mechanism, validated by TD-DFT analysis, demonstrates controllable fluorescence and phosphorescence by modulating the π-twisting feasibility of the central C═C bond, offering a novel strategy for designing advanced aggregation-induced emission (AIE) and RTP-active molecules.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"6163-6169"},"PeriodicalIF":4.9,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144207196","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 Double 1,2-Carbon Migration toward All-Carbon Tetrasubstituted Olefins. 光诱导双1,2-碳向全碳四取代烯烃迁移。
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-06-13 Epub Date: 2025-06-04 DOI: 10.1021/acs.orglett.5c01982
Tianyu He, Chao Kong, Yukai Liu, Yu Zheng, Yanju Lu, Xiaoxiang Zhang, Shenlin Huang
{"title":"Photoinduced Double 1,2-Carbon Migration toward All-Carbon Tetrasubstituted Olefins.","authors":"Tianyu He, Chao Kong, Yukai Liu, Yu Zheng, Yanju Lu, Xiaoxiang Zhang, Shenlin Huang","doi":"10.1021/acs.orglett.5c01982","DOIUrl":"10.1021/acs.orglett.5c01982","url":null,"abstract":"<p><p>A photochemical double 1,2-carbon migration approach was achieved as an efficient entry into all-carbon tetrasubstituted olefins from allenols. Key to the success is the use of FSO<sub>2</sub>Cl, which plays a crucial triple role as an effective Cl<sup>+</sup> synthon to facilitate semipinacol rearrangement, an electron acceptor to form electron donor-acceptor complexes, and a FSO<sub>2</sub><sup>•</sup> precursor to trigger 1,2-carbonyl migration. The synthetic utility is further showcased by extending it to other radical precursors and diverse follow-up reactions.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"6244-6249"},"PeriodicalIF":4.9,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144214361","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
Strategic Acetylation of BODIPY Dyes: Tuning Excited-State Geometry for the Design of Fluorogenic Sensing Probes BODIPY染料的策略乙酰化：调整荧光传感探针设计的激发态几何
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-06-13 DOI: 10.1021/acs.orglett.5c01822
Yeri Kim, Youngmi Kim
{"title":"Strategic Acetylation of BODIPY Dyes: Tuning Excited-State Geometry for the Design of Fluorogenic Sensing Probes","authors":"Yeri Kim, Youngmi Kim","doi":"10.1021/acs.orglett.5c01822","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01822","url":null,"abstract":"Strategic acetylation and alkylation modulate the photophysical properties of BODIPY dyes. <i>Meso</i>-acetylated <b>D8COMe</b> exhibits a large Stokes shift through excited-state geometric reorganization, while C2-acetylated <b>D2COMe</b> preserves characteristic BODIPY spectral features. Introduction of methyl groups at the C1/C7 positions influences fluorescence efficiency, with <b>T8COMe</b> showing viscosity-dependent emission. Computational analyses confirm structural distortion as the primary mechanism for fluorescence modulation. These structure–property relationships enable the rational design of fluorogenic probes for nucleophilic species detection and viscosity sensing applications.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144278644","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
Total Synthesis of Pedopeptin C 培肽C的全合成
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-06-13 DOI: 10.1021/acs.orglett.5c01928
Michael J. Lambrecht, Ying Lu, Mary Kate Alexander, Daniel J. Burdick, Chen Cheng, Tommy Lai, Steven T. Rutherford, Qiuyue Wang, Jiao Xu, Michael F. T. Koehler
{"title":"Total Synthesis of Pedopeptin C","authors":"Michael J. Lambrecht, Ying Lu, Mary Kate Alexander, Daniel J. Burdick, Chen Cheng, Tommy Lai, Steven T. Rutherford, Qiuyue Wang, Jiao Xu, Michael F. T. Koehler","doi":"10.1021/acs.orglett.5c01928","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01928","url":null,"abstract":"The pedopeptins are a class of antibiotics that have been reported to retain activity against bacterial strains that are resistant to the polymyxins, a class of antibiotics of last resort. Despite this promising activity, the pedopeptins represent synthetically challenging targets due to the dehydroamino acid (<i>E</i>)-2-aminobut-2-enoic acid ((<i>E</i>)-ΔAbu) contained in their structure. Here we show an optimized synthesis of a lead member of this class, pedopeptin C, and describe its antibacterial activity.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"35 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144278475","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
Application of Indolyl Ynones in the Construction of Chiral Carbazoles and Pyrroloindolines by Organo and Metal Sequential Catalysis. 吲哚酮在手性咔唑和吡咯啉的有机和金属顺序催化合成中的应用。
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-06-13 Epub Date: 2025-06-04 DOI: 10.1021/acs.orglett.5c01900
Qing-Qing Li, Qian-Jun Lin, Yi Gao, Wen-Jing Xiao, Xue-Qing Song, Longfei Li, Wan Li, Ya-Li Song, Zhi-Hao You
{"title":"Application of Indolyl Ynones in the Construction of Chiral Carbazoles and Pyrroloindolines by Organo and Metal Sequential Catalysis.","authors":"Qing-Qing Li, Qian-Jun Lin, Yi Gao, Wen-Jing Xiao, Xue-Qing Song, Longfei Li, Wan Li, Ya-Li Song, Zhi-Hao You","doi":"10.1021/acs.orglett.5c01900","DOIUrl":"10.1021/acs.orglett.5c01900","url":null,"abstract":"<p><p>The enantioselective synthesis of carbazoles and pyrroloindolines has been achieved through organo-catalyzed and metal sequential-catalyzed one-pot reactions of indolyl ynones. Chiral carbazoles can be synthesized from the reactions of indolyl ynones and nitroolefins through an organo-catalyzed Michael addition followed by a gold-catalyzed Friedel-Crafts reaction/aromatization process. The reactions of indolyl ynones and N-tosyl imines lead to the generation of pyrroloindolines via an organo-catalyzed Mannich reaction and a silver-catalyzed dearomatizing spirocyclization/N,N-acetalization cascade reaction.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"6216-6221"},"PeriodicalIF":4.9,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144214359","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 Aminocarbonylation Using Nitroarenes under NMP-Mediated Photochemical Conditions 在nmp介导的光化学条件下钯催化硝基芳烃氨基羰基化
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-06-13 DOI: 10.1021/acs.orglett.5c01619
Minwoo Park, Karthik Rajan Rajamanickam, Sunwoo Lee
{"title":"Palladium-Catalyzed Aminocarbonylation Using Nitroarenes under NMP-Mediated Photochemical Conditions","authors":"Minwoo Park, Karthik Rajan Rajamanickam, Sunwoo Lee","doi":"10.1021/acs.orglett.5c01619","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01619","url":null,"abstract":"A photochemical approach enabling mild amide synthesis from aryl iodides, carbon monoxide, and nitroarenes at 25 °C under 1 atm of CO is disclosed. Under a PdCl<sub>2</sub>/Xantphos–FeCl<sub>3</sub> catalyst in <i>N</i>-methylpyrrolidone, broad functional group tolerance is observed. Mechanistic studies reveal that nitroarenes form a base-activated <i>N</i>-methylpyrrolidone-bound adduct, which generates an aniline-like intermediate that couples with the acyl–palladium complex to deliver the desired amides.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"4 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144278640","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
Mild Lewis-Acid-Promoted Cysteine-Tryptophan Conjugation Involving a Radical Process. 轻度lewis酸促进半胱氨酸-色氨酸偶联涉及自由基过程。
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-06-13 Epub Date: 2025-06-04 DOI: 10.1021/acs.orglett.5c01845
Qingqing Lu, Hongyan Wen, Qinshuo Zhang, Zhou Zhang, Shiping Wang, Ruo Wang, Chunfa Xu
{"title":"Mild Lewis-Acid-Promoted Cysteine-Tryptophan Conjugation Involving a Radical Process.","authors":"Qingqing Lu, Hongyan Wen, Qinshuo Zhang, Zhou Zhang, Shiping Wang, Ruo Wang, Chunfa Xu","doi":"10.1021/acs.orglett.5c01845","DOIUrl":"10.1021/acs.orglett.5c01845","url":null,"abstract":"<p><p>Numerous methods have been developed for peptide synthesis due to their great potential in drug discovery. However, the technique for tryptophan-cysteine conjugation is still underexplored. Herein, we present a TMSBr-promoted ligation of tryptophan and cysteine under mild conditions by using a sulfonate-modified cysteine substrate. This protocol features a broad scope and high site selectivity and is applicable for synthesis of cyclic peptide. Preliminary mechanistic studies reveal that the reaction proceeds via a radical process.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"6192-6197"},"PeriodicalIF":4.9,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144214360","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
Elucidation of a Parasitic Proton-Coupled Electron Transfer in a Photocatalytic Benzylic C-H Sulfonamidation. 光催化苄基C-H磺化反应中寄生质子耦合电子转移的研究。
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-06-13 Epub Date: 2025-06-03 DOI: 10.1021/acs.orglett.5c01637
Nicholas A Fitzpatrick, Anna M Howarth, Grzegorz J Skrzypek, Jisun Lee, Hatice G Yayla, Patricia Z Musacchio
{"title":"Elucidation of a Parasitic Proton-Coupled Electron Transfer in a Photocatalytic Benzylic C-H Sulfonamidation.","authors":"Nicholas A Fitzpatrick, Anna M Howarth, Grzegorz J Skrzypek, Jisun Lee, Hatice G Yayla, Patricia Z Musacchio","doi":"10.1021/acs.orglett.5c01637","DOIUrl":"10.1021/acs.orglett.5c01637","url":null,"abstract":"<p><p>Strategies for C-H amination with sulfonamides have been dominated by stoichiometric strategies or Rh/Cu catalysis using strong oxidants, elevated temperatures, or excess equivalents of C-H partner. We developed a photocatalytic C-H amination with a bench-stable <i>N</i>-methoxypyridinium salt that is amenable to late-stage functionalization efforts. We discovered a competitive proton-coupled electron transfer pathway between sulfonamide and a pyridine byproduct that inhibits the reaction. Catalysis was re-established with the introduction of ZnBr<sub>2</sub>.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"6065-6070"},"PeriodicalIF":4.9,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144207194","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
Base-Mediated Formal Denitrogenative Insertion of Nonactivated Triazoles into Aldehydes: Stereospecific Synthesis of Highly Substituted Acrylamides. 碱基介导的非活化三唑正式脱氮插入醛：立体定向合成高取代丙烯酰胺。
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-06-13 DOI: 10.1021/acs.orglett.5c02157
Liguo Teng, Shaofan Wang, Wenxiang Zhu, Xian Dong, Tiebo Xiao, Guiping Qin, Edward A Anderson, Yubo Jiang
{"title":"Base-Mediated Formal Denitrogenative Insertion of Nonactivated Triazoles into Aldehydes: Stereospecific Synthesis of Highly Substituted Acrylamides.","authors":"Liguo Teng, Shaofan Wang, Wenxiang Zhu, Xian Dong, Tiebo Xiao, Guiping Qin, Edward A Anderson, Yubo Jiang","doi":"10.1021/acs.orglett.5c02157","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c02157","url":null,"abstract":"<p><p>A base-mediated denitrogenative insertion of nonactivated <i>N(1)</i>-aryl-1,2,3-triazoles into aldehydes to construct trisubstituted (<i>E</i>)-acrylamides was developed. The reaction, which involves formal insertion of two atoms from the triazole into the aldehyde C═O bond with concomitant loss of nitrogen, proceeds at ambient temperature with complete stereocontrol. This method provides a highly efficient and straightforward means to construct functionalized acrylamides by employing readily available 1,2,3-triazoles and aldehydes as starting materials.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144281721","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
Phosphine-Catalyzed Asymmetric Dearomative Annulation of 4-Nitroisoxazoles with Allenoates: Construction of Isoxazoline-Fused Bicyclo[3.3.0]octenes. 膦催化4-硝基异恶唑与烯丙酸酯的不对称脱芳环化：异恶唑-融合双环[3.3.0]辛烯的构建
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-06-13 DOI: 10.1021/acs.orglett.5c01958
Huamin Wang, Hong-Ding Xie, Jun-Long Ding, Yanjun Xie, Ying-Wu Lin, Junliang Zhang
{"title":"Phosphine-Catalyzed Asymmetric Dearomative Annulation of 4-Nitroisoxazoles with Allenoates: Construction of Isoxazoline-Fused Bicyclo[3.3.0]octenes.","authors":"Huamin Wang, Hong-Ding Xie, Jun-Long Ding, Yanjun Xie, Ying-Wu Lin, Junliang Zhang","doi":"10.1021/acs.orglett.5c01958","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01958","url":null,"abstract":"<p><p>An intermolecular phosphine-catalyzed dearomatization reaction of 4-nitroisoxazoles with allenoates was realized through one-pot sequential [3 + 2]/[3 + 2] annulation. Various isoxazoline-fused bicyclo[3.3.0]octene derivatives were successfully synthesized in good to excellent yields (up to 98%). Under catalysis with <b>SadPhos P7</b>, enantioselective dearomative cyclization occurred, initiating the subsequent [3 + 2] cycloaddition process to afford valuable optically active cyclopentane-fused polycyclic scaffolds bearing a quaternary carbon stereocenter in 58-98% yields with 70-97% ee. The synthetic utility of this protocol was demonstrated by the gram-scale reaction and versatile transformations of the product.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144281724","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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