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Synthesis ofα-Cyano-β-naphthylaminesvia Tandem Selective Hydrocyanation of Unactivated Alkynes and ThorpeReaction 非活化炔烃串联选择性氢化反应合成α-氰基-β-萘胺
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-14 DOI: 10.1021/acs.orglett.6c04271
Weiming Chen,Teng Liu,Tao Zhu,Lechi Zhang,Qilinjing Li,Yiwen Wang,Zishuo Li,Rongxin Su,Junyuan Hu,Jiuzhong Huang
{"title":"Synthesis of\u0000α-Cyano-β-naphthylamines\u0000via Tandem Selective Hydrocyanation of Unactivated Alkynes and Thorpe\u0000Reaction","authors":"Weiming Chen,Teng Liu,Tao Zhu,Lechi Zhang,Qilinjing Li,Yiwen Wang,Zishuo Li,Rongxin Su,Junyuan Hu,Jiuzhong Huang","doi":"10.1021/acs.orglett.6c04271","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04271","url":null,"abstract":"Abstract An unprecedented nickel-catalyzed tandem reaction involving alkyne hydrocyanation and sequential Thorpe reaction has been developed. By employing readily available and less toxic Zn(CN)2 as the cyanide source, both selective alkyne hydrocyanation and tandem cyclization are achieved in a substrate-controlled manner. Mechanistic studies and DFT calculations confirm that the alkenyl nitrile serves as a key intermediate, and hydrogen transfer is identified as the rate-determining step in the Thorpe reaction. This work offers a novel strategy for the construction of α-cyano-β-naphthylamine via a cascade reaction mode.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"63 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209533","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
MultidimensionalInvolvement of Tris(4-methoxyphenyl)aminein Electrolytic Sulfonylation of Alkenes 三（4-甲氧基苯基）胺在烯烃电解磺化反应中的多维参与
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-14 DOI: 10.1021/acs.orglett.6c04101
Yangkai Dong,Yuchen Li,Yutong Wang,Jichao Yu,Baoshun Huang,Jiabo Wang,Yuan-Ye Jiang,Yulei Zhao
{"title":"Multidimensional\u0000Involvement of Tris(4-methoxyphenyl)amine\u0000in Electrolytic Sulfonylation of Alkenes","authors":"Yangkai Dong,Yuchen Li,Yutong Wang,Jichao Yu,Baoshun Huang,Jiabo Wang,Yuan-Ye Jiang,Yulei Zhao","doi":"10.1021/acs.orglett.6c04101","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04101","url":null,"abstract":"Abstract A tris(4-methoxyphenyl)amine (TMPA)-catalyzed paired-electrolysis sulfonylation is reported. TMPA first serves as the electron donor, thereby facilitating the reduction of sulfonyl chloride; subsequently, the resulting TMPA•+ oxidizes the benzyl radical intermediate. TMPA and the chloride anion also act as a Brønsted base to promote deprotonation at the α-carbon of the sulfonyl group. The current results elucidate a novel paradigm of triarylamine multiple activation, which may stimulate continuous exploration of multiple action modes of other mediators.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"4 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209534","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
Controlled Generationof Unstabilized N -Alkyl Nitrile Imines EnablesRegioselective (3 + 2) Cycloadditionswith Diverse Dipolarophiles 控制生成不稳定的N -烷基腈亚胺使区域选择性（3 + 2）环加成物具有不同的亲偶极试剂
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-14 DOI: 10.1021/acs.orglett.6c03912
Matthew C. Lamb,Tristan H. Lambert
{"title":"Controlled Generation\u0000of Unstabilized\u0000 N\u0000 -Alkyl Nitrile Imines Enables\u0000Regioselective (3 + 2) Cycloadditions\u0000with Diverse Dipolarophiles","authors":"Matthew C. Lamb,Tristan H. Lambert","doi":"10.1021/acs.orglett.6c03912","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03912","url":null,"abstract":"Abstract N-Alkyl nitrile imines remain underdeveloped as intermediates for intermolecular cycloadditions. Here, we report their in situ generation and regioselective (3 + 2) cycloaddition with activated and unactivated alkenes and alkynes, affording N-alkyl pyrazolines and pyrazoles in good to excellent yields. The method accommodates broad variation in both reaction partners and enables gram-scale preparation of a key pyrazole fragment used in the synthesis of lenacapavir in a 79% yield over two steps.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"48 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209561","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
PhotocatalyticScaffold Hopping of Cyclobutanols toCyclopentanols via Single-Carbon Insertion into C–C σ-Bonds 通过C-C σ-键单碳插入环丁醇到环戊醇的光催化支架跳变
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-14 DOI: 10.1021/acs.orglett.6c04162
Xuyang Wang,Can Wang,Yongmin Ma,Peng Zhao
{"title":"Photocatalytic\u0000Scaffold Hopping of Cyclobutanols to\u0000Cyclopentanols via Single-Carbon Insertion into C–C σ-Bonds","authors":"Xuyang Wang,Can Wang,Yongmin Ma,Peng Zhao","doi":"10.1021/acs.orglett.6c04162","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04162","url":null,"abstract":"Abstract A method for skeletal editing of C–C σ-bonds in strained alicycles via single-carbon insertion is reported. This skeletal editing method for cyclobutanols differs from well-established semipinacol rearrangement pathways, offering an efficient route to cyclopentanols by direct scaffold hopping of cyclobutanols. This transformation proceeds under mild conditions in good yields, expanding the toolkit for single-atom insertion into C–C σ-bonds.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"40 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209560","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
StereoselectiveSynthesis of Linustedastat Via Deoxy-AromatizationStrategy 用脱氧芳构化策略立体选择性合成linusteastat
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-14 DOI: 10.1021/acs.orglett.6c03795
Santhosh Reddy Naini,Tony Hudgens,Luis Sierra,Leena Hirvelä,Anji Chen,Chengfeng Ye,Huiping Zhao,Xueyi Zhang,Madhusudhan Reddy Gadi,Mohammed Sharique,Jiezhen Li,Rahul D. Shingare,Praveen Gajula,Nageswara Kalikinidi,Manasa Mamunooru,Jonathan Bietsch,Zhirui Wang,Rajender Reddy Leleti,Bo Qu,Chris H. Senanayake
{"title":"Stereoselective\u0000Synthesis of Linustedastat Via Deoxy-Aromatization\u0000Strategy","authors":"Santhosh Reddy Naini,Tony Hudgens,Luis Sierra,Leena Hirvelä,Anji Chen,Chengfeng Ye,Huiping Zhao,Xueyi Zhang,Madhusudhan Reddy Gadi,Mohammed Sharique,Jiezhen Li,Rahul D. Shingare,Praveen Gajula,Nageswara Kalikinidi,Manasa Mamunooru,Jonathan Bietsch,Zhirui Wang,Rajender Reddy Leleti,Bo Qu,Chris H. Senanayake","doi":"10.1021/acs.orglett.6c03795","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03795","url":null,"abstract":"Abstract An efficient and stereoselective synthesis of Linustedastat (1) is reported, commencing from inexpensive and commercially available sitolactone. The route features a highly chemoselective Grignard addition, followed by sequential double aldol condensations to construct the core steroidal framework. A key step involves a novel deoxy-aromatization of a fluorinated steroid intermediate, setting the stage for a stereoselective hydrogenation and a 1,4-conjugate addition to further elaborate the molecule. This strategically designed sequence delivers the complex and electron-deficient fluorinated steroidal architecture in 16 steps with an 11.0% overall yield.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"10 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209556","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
Pd-CatalyzedFreon-Enabled Aminocarbonylation of ArylIodides 钯催化的芳烷酰化的氟利昂使能氨基羰基化
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-14 DOI: 10.1021/acs.orglett.6c03872
Yu Guo,Shuai Su,Yixue Lei,Jianke Su,Qiuling Song
{"title":"Pd-Catalyzed\u0000Freon-Enabled Aminocarbonylation of Aryl\u0000Iodides","authors":"Yu Guo,Shuai Su,Yixue Lei,Jianke Su,Qiuling Song","doi":"10.1021/acs.orglett.6c03872","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03872","url":null,"abstract":"Abstract A palladium-catalyzed Freon-to-carbonyl transfer strategy has been developed for the CO-free aminocarbonylation of aryl and heteroaryl iodides with amines. Using chlorodifluoromethane (Freon-22) as both a difluorocarbene precursor and a carbonyl source, this protocol enables direct access to diverse benzamide derivatives without external CO gas or conventional CO-releasing reagents. The reaction exhibits a broad substrate scope and good functional-group tolerance, accommodating electronically diverse aryl iodides, polycyclic and heteroaryl iodides, and primary and secondary amines. Its synthetic utility is demonstrated by late-stage benzamidation of bioactive-molecule-derived substrates and concise synthesis of pharmaceutically relevant benzamide scaffolds, including trimethobenzamide and methyl tamibarotene. Mechanistic experiments involving benzimidazole trapping and H218O labeling support a difluorocarbene-derived carbonyl-transfer process in which water contributes to the oxygen atom of the amide carbonyl group. This work establishes Freon-22 as a practical carbonyl surrogate for CO-free amide synthesis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"292 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209555","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
Solid-PhaseSynthesis of Enteropeptin A Analogues 肠肽A类似物的固相合成
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-14 DOI: 10.1021/acs.orglett.6c04116
Karen D. Milewska,Fletcher M. Sharp,Lara R. Malins
{"title":"Solid-Phase\u0000Synthesis of Enteropeptin A Analogues","authors":"Karen D. Milewska,Fletcher M. Sharp,Lara R. Malins","doi":"10.1021/acs.orglett.6c04116","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04116","url":null,"abstract":"Abstract Enteropeptin A is a sactipeptide natural product featuring a unique six-membered thiomorpholine core. Herein, we describe a solid-phase peptide synthesis (SPPS)-compatible approach to enteropeptin A analogues featuring a simplified sactionine motif. The strategy employs a readily accessible building block and efficient on-resin assembly. A “N to C” variant, differing in the directionality of the sactionine linkage was also readily accessible. Collectively, this work accelerates access to analogues of this important class of natural products.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"51 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209558","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
Planar Bis(1,3,4-Oxadiazole)Bridging toward High-Energyand Low-Sensitivity Tetracyclic Compounds 平面双（1,3,4-恶二唑）桥接高能量低灵敏度四环化合物
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-14 DOI: 10.1021/acs.orglett.6c03949
Jing Liu,Miao Li,Zhiwei Zeng,Wei Huang,Guangbin Cheng,Yuji Liu,Chuan Xiao,Yongxing Tang
{"title":"Planar Bis(1,3,4-Oxadiazole)\u0000Bridging toward High-Energy\u0000and Low-Sensitivity Tetracyclic Compounds","authors":"Jing Liu,Miao Li,Zhiwei Zeng,Wei Huang,Guangbin Cheng,Yuji Liu,Chuan Xiao,Yongxing Tang","doi":"10.1021/acs.orglett.6c03949","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03949","url":null,"abstract":"Abstract A planar bis(1,3,4-oxadiazole) bridging strategy was developed to access rigid, extended-conjugated tetracyclic energetic compounds. Incorporation of this bridge into two distinct energetic scaffolds afforded 4 and 7. Single-crystal X-ray diffraction revealed a nearly planar bis(1,3,4-oxadiazole) bridge in both compounds, accompanied by extended π-electron delocalization across the molecular frameworks. Compound 4 showed enhanced thermal and mechanical stability, while 7 combined improved energetic performance with increased stability.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"160 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209562","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
Dihydrogen PhosphateAnion-Templated Synthesis ofUrethane-Based Macrocycle Containing Perfluoroalkyl Chain 磷酸二氢阴离子模板法合成含全氟烷基链呋喃基大环
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-14 DOI: 10.1021/acs.orglett.6c03944
Xiao Zhang,Fengying Liang,Yanqing Du,Mixia Hu,Chaolong Bi,Wenwang Wang,Chunxia Liu,Mingxue Bai,Chaolu Eerdun,Akihiko Tsuda
{"title":"Dihydrogen Phosphate\u0000Anion-Templated Synthesis of\u0000Urethane-Based Macrocycle Containing Perfluoroalkyl Chain","authors":"Xiao Zhang,Fengying Liang,Yanqing Du,Mixia Hu,Chaolong Bi,Wenwang Wang,Chunxia Liu,Mingxue Bai,Chaolu Eerdun,Akihiko Tsuda","doi":"10.1021/acs.orglett.6c03944","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03944","url":null,"abstract":"Abstract The efficient synthesis of macrocycles has been a challenging subject in supramolecular chemistry. This study shows that H2PO4– acts as a template in the synthesis of novel macrocycles containing a long perfluoroalkyl chain in their backbone. Density functional theory (DFT) calculations indicate that H2PO4– preorganizes the reaction intermediate in the transition state through multiple hydrogen-bonding interactions, promoting the cyclization reaction and increasing the yield of the macrocycle. The introduction of the fluoroalkyl chain increases the acidity of the neighboring CH2 group, thereby enhancing the hydrogen-bonding interactions in the intermediate complex.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"1 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209564","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
Scaffold Hoppingof Pyrimidines into 2-Acylpyrroles 嘧啶支架跳跃成2-酰基吡咯
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-14 DOI: 10.1021/acs.orglett.6c03859
Enxian Li,Cong Lv,Shunyao Huang,Yonglin Shi,Shenxiang Wang,Weichao Xue,Xueli Zheng,Hua Chen,Ruixiang Li,Haiyan Fu
{"title":"Scaffold Hopping\u0000of Pyrimidines into 2-Acylpyrroles","authors":"Enxian Li,Cong Lv,Shunyao Huang,Yonglin Shi,Shenxiang Wang,Weichao Xue,Xueli Zheng,Hua Chen,Ruixiang Li,Haiyan Fu","doi":"10.1021/acs.orglett.6c03859","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03859","url":null,"abstract":"Abstract A practical skeletal-editing strategy was developed for the conversion of 4-substituted pyrimidines into 2-acyl-5-arylpyrroles. The transformation directly converts a six-membered, electron-deficient pyrimidine into a five-membered azole while simultaneously installing an acyl group. The reaction sequence involves pyrimidine activation, ring-opening, fragmentation, and ring reconstruction. Central to this strategy is the controlled generation of pyrimidine-derived vinamidinium salts as open-chain A4 synthons, which are then intercepted by α-bromoketones as functionalized annulation reagents. The developed scaffold-hopping method can be applied for late-stage modification of pyrimidine-containing bioactive or pharmaceutical molecules.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"86 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209532","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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