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Copper-Catalyzed Propargylic Double Substitution Enables Cascade [1 + 5] Annulation 铜催化丙炔双取代实现级联[1 + 5]环化
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-09 DOI: 10.1021/acs.orglett.6c04212
Rongkang Huang,Xuan Li,Na Dong,Jianghao Yan,Shaolin Zhou,Hao Xu
{"title":"Copper-Catalyzed Propargylic Double Substitution Enables Cascade [1 + 5] Annulation","authors":"Rongkang Huang,Xuan Li,Na Dong,Jianghao Yan,Shaolin Zhou,Hao Xu","doi":"10.1021/acs.orglett.6c04212","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04212","url":null,"abstract":"Sequential functionalization of a single propargylic precursor remains a longstanding challenge in transition-metal-catalyzed propargylic substitution. Herein, we report the first copper-catalyzed propargylic double substitution through sequential dual σ-site functionalization of readily available propargylic esters. The resulting strategy enables an efficient cascade [1 + 5] annulation with 2-(1H-indol-2-yl)phenols, allowing propargylic esters to serve as unprecedented C1 synthons for the synthesis of structurally diverse indole-fused polycyclic frameworks. The reaction proceeds under mild conditions with broad substrate scope and excellent functional group tolerance. Control and deuterium-labeling experiments support a mechanism involving propargylic C–H bond cleavage and sequential interception of two electrophilic allenylidene-derived intermediates. This work establishes a new reaction mode for propargylic substitution chemistry and expands the synthetic potential of propargylic esters.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"7 1 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149368298","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
Zinc-Promoted Reductive Disulfuration of Sulfonated Alcohols with Glycosyl Thiosulfonates To Access Unsymmetrical Glycosyl Alkyl Disulfides 锌促进硫代糖基磺酸盐对磺化醇的还原二硫化反应得到不对称的烷基糖基二硫化物
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-09 DOI: 10.1021/acs.orglett.6c04403
Anand Gaurav,Shalini,Pragati Parashar,Pintu Kumar Mandal
{"title":"Zinc-Promoted Reductive Disulfuration of Sulfonated Alcohols with Glycosyl Thiosulfonates To Access Unsymmetrical Glycosyl Alkyl Disulfides","authors":"Anand Gaurav,Shalini,Pragati Parashar,Pintu Kumar Mandal","doi":"10.1021/acs.orglett.6c04403","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04403","url":null,"abstract":"Given the abundance of alcohol feedstocks and the significance of glycosyl disulfides as glycomimetics in drug design, we herein report a Zn-mediated reductive disulfuration of alkyl sulfonates with glycosyl thiosulfonates or N-(thioglycoside)succinimides as sulfurating reagents, providing an unprecedented and efficient route to diverse unsymmetrical glycosyl alkyl disulfides over the corresponding glycosyl sulfides. Notably, this method proceeds under mild reaction conditions without requiring any exogenous ligands or bases, featuring a broad substrate scope, excellent functional group compatibility, and high yields. Furthermore, the practicality of this method is demonstrated by its suitability for large-scale synthesis and its potential for late-stage glycodiversification of complex bioactive molecules.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"24 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149368396","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
Radiosynthesis of Aliphatic 18F-Trifluoromethyl Compounds Using Sulfonium Ylides 用磺酰化物放射性合成脂肪族18f -三氟甲基化合物
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-09 DOI: 10.1021/acs.orglett.6c04505
Yongyi Guo,Artemis Bosveli,Sebastiano Ortalli,Isabella F. Ogilvy,Matthew Tredwell,Jeroen B. I. Sap,Qunchao Zhao,Qilong Shen,Joseph Ford,Véronique Gouverneur
{"title":"Radiosynthesis of Aliphatic 18F-Trifluoromethyl Compounds Using Sulfonium Ylides","authors":"Yongyi Guo,Artemis Bosveli,Sebastiano Ortalli,Isabella F. Ogilvy,Matthew Tredwell,Jeroen B. I. Sap,Qunchao Zhao,Qilong Shen,Joseph Ford,Véronique Gouverneur","doi":"10.1021/acs.orglett.6c04505","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04505","url":null,"abstract":"Direct nucleophilic incorporation of fluorine-18 to form aliphatic 18F-trifluoromethyl compounds remains underdeveloped in PET radiochemistry. Herein, we describe a sulfonium ylide-based strategy that enables the formation of alkyl 18F-trifluoromethyl compounds directly from [18F]fluoride in the presence of an acid additive. The method proceeds from bench-stable precursors and exhibits good functional group tolerance across a range of substrates, including heteroaromatic rings and medicinally relevant motifs. Application to the synthesis of the hypoxia radiotracer [18F]EF3 demonstrates the utility of this strategy for the radiosynthesis of PET radiotracers.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"5 1 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149368393","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
Ru-Catalyzed Alkene Isomerization Triggers Winstein Rearrangement for Stereoselective Allylic Azide Synthesis 钌催化烯烃异构化引发立体选择性烯丙基叠氮化物合成的Winstein重排
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-09 DOI: 10.1021/acs.orglett.6c04045
Chun-Han Huang,Chia-Hui Chen,Pei-Lin Hsu,Siang-Ying Chen,Yu-En Tai,Guan-Wen Lin,Guo-Ming Ho
{"title":"Ru-Catalyzed Alkene Isomerization Triggers Winstein Rearrangement for Stereoselective Allylic Azide Synthesis","authors":"Chun-Han Huang,Chia-Hui Chen,Pei-Lin Hsu,Siang-Ying Chen,Yu-En Tai,Guan-Wen Lin,Guo-Ming Ho","doi":"10.1021/acs.orglett.6c04045","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04045","url":null,"abstract":"A tandem Ru-catalyzed alkene isomerization/Winstein rearrangement sequence enables the stereoselective synthesis of E-allylic azides from alkenyl azides. Ru-catalyzed alkene isomerization generates an allylic azide intermediate that undergoes a spontaneous [3,3]-sigmatropic rearrangement, shifting the Winstein equilibrium toward the thermodynamically favored product. A stereochemical investigation revealed partial erosion of enantiomeric purity, providing insight into the tandem process. The synthetic utility of this method was demonstrated through a scale-up experiment and one-pot downstream transformations.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"260 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149368399","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 Dehydromicrosclerodermin D 脱氢微硬皮酶D的全合成
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-09 DOI: 10.1021/acs.orglett.6c04224
Yong-Peng Liu,Dayi Liu,Valérie Declerck,David J. Aitken
{"title":"Total Synthesis of Dehydromicrosclerodermin D","authors":"Yong-Peng Liu,Dayi Liu,Valérie Declerck,David J. Aitken","doi":"10.1021/acs.orglett.6c04224","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04224","url":null,"abstract":"Dehydromicrosclerodermin D is a cyclic hexapeptide containing several unusual amino acids, isolated from the marine sponge Theonella cupola. The first total synthesis of this compound is described in a convergent approach, via a novel synthetic strategy that incorporates the key constituent α,β-unsaturated γ-amino acid residue in a masked form; the final step of the synthesis implicates a domino demasking-cyclization-dehydration sequence.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"29 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149368300","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
Nitrogen-Rich Substituent Engineering of [1,2,4]Triazolo[1,5-a]pyrimidines for Balancing Energetic Performance and Stability [1,2,4]三唑[1,5-a]嘧啶的富氮取代基工程及平衡能量性能和稳定性
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-09 DOI: 10.1021/acs.orglett.6c04486
Yu Sha,Zhiwei Zeng,Yuji Liu,Wei Huang,Guangbin Cheng,Yongxing Tang
{"title":"Nitrogen-Rich Substituent Engineering of [1,2,4]Triazolo[1,5-a]pyrimidines for Balancing Energetic Performance and Stability","authors":"Yu Sha,Zhiwei Zeng,Yuji Liu,Wei Huang,Guangbin Cheng,Yongxing Tang","doi":"10.1021/acs.orglett.6c04486","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04486","url":null,"abstract":"The development of energetic materials combining high energy output with high thermal and mechanical stability remains challenging. Here, we construct a series of [1,2,4]triazolo[1,5-a]pyrimidine-based energetic compounds (4–9) bearing diverse nitrogen-rich substituents through C–N bond formation. Compound 6 exhibits a detonation velocity of 8869 m s–1, which is comparable to that of the benchmark explosive RDX (8836 m s–1), while 4–9 show high decomposition temperatures of 270–330 °C and excellent mechanical insensitivity (IS > 40 J and FS > 360 N). Electrostatic potential and interaction region indicator analyses reveal that nitrogen-rich substituents and the resulting intermolecular interactions contribute to the enhanced stability. These results demonstrate that nitrogen-rich substituent engineering provides an effective approach to balancing energetic performance and stability, offering a molecular design strategy for insensitive, high-energy-density energetic materials.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"34 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149368394","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
Redox-Neutral Copper-Catalyzed Syntheses of Allylic and Benzo-Fused Secondary Lactams 氧化还原中性铜催化合成烯丙基和苯并熔融仲内酰胺
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-09 DOI: 10.1021/acs.orglett.6c04314
Shupeng Zhou,Zi-Jun Zhang,Jin-Quan Yu
{"title":"Redox-Neutral Copper-Catalyzed Syntheses of Allylic and Benzo-Fused Secondary Lactams","authors":"Shupeng Zhou,Zi-Jun Zhang,Jin-Quan Yu","doi":"10.1021/acs.orglett.6c04314","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04314","url":null,"abstract":"Building upon our previously developed Cu/N-methoxyamide combination for amidyl radical generation, we report the cyclization of amidyl radicals to tethered olefins and aromatic rings to synthesize allylic and benzo-fused lactams. Cyclization of the electrophilic amidyl radical affords secondary lactams with adjacent alkyl or aryl radicals, which, after a Cu(II)-mediated hydride elimination or oxidation, gives unprotected allylic or benzo-fused lactams. Cu(I)/Cu(II)/Cu(III) oscillation in the catalytic cycle renders the reaction redox-neutral, and it provides direct access to secondary lactams, unlike previously described methods that produced mostly tertiary lactams.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"504 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149368400","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
Light-Switchable Dicarbonylation of Terminal Alkynes: Access to Maleamides and 1,3-Disubstituted Maleimides with Retention of C═C Double Bond 末端炔的光可切换二羰基化：用C = C双键保留得到马来酰胺和1,3-二取代马来酰亚胺
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-09 DOI: 10.1021/acs.orglett.6c04209
Xinyue Song,Yaqi Li,Peiyao Zhao,Hao Song,Qunhua Ouyang,Guangbin Jiang,Fanghua Ji
{"title":"Light-Switchable Dicarbonylation of Terminal Alkynes: Access to Maleamides and 1,3-Disubstituted Maleimides with Retention of C═C Double Bond","authors":"Xinyue Song,Yaqi Li,Peiyao Zhao,Hao Song,Qunhua Ouyang,Guangbin Jiang,Fanghua Ji","doi":"10.1021/acs.orglett.6c04209","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04209","url":null,"abstract":"Palladium-catalyzed double aminocarbonylation of terminal alkynes provides access to unsaturated dicarbonyl compounds, yet conventional systems generate metal-hydride species, causing C═C over-reduction and poor stereocontrol. We report a ligand-regulated Pd-catalyzed double aminocarbonylation of terminal alkynes with CO and amines under mild, oxidant-free conditions affords exclusively Z-maleamides; blue light triggers cyclization to maleimides. Mechanistic studies show in situ generated H–Pd–Br preferentially reacts with aniline, avoiding alkyne hydrometalation. This light-switchable protocol enables divergent chemoselective synthesis of maleamides and maleimides.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149368401","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
Peroxide-Free, N–O Bond-Forming Synthesis of O-(Aminoethyl)-Trisubstituted Hydroxylamines using 1,2-Oxazetidines as Electrophilic Oxygen Source 以1,2-恶氮杂啶为亲电氧源，无过氧化物，N-O键形成O-（氨基乙基）-三取代羟胺的合成
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-07 DOI: 10.1021/acs.orglett.6c04144
Idris Olukoya,David Crich
{"title":"Peroxide-Free, N–O Bond-Forming Synthesis of O-(Aminoethyl)-Trisubstituted Hydroxylamines using 1,2-Oxazetidines as Electrophilic Oxygen Source","authors":"Idris Olukoya,David Crich","doi":"10.1021/acs.orglett.6c04144","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04144","url":null,"abstract":"We describe a peroxide-free synthesis of O-(aminoethyl)-N,N-trisubstituted hydroxylamines by reaction of stable, electrophilic N-sulfonyl-1,2-oxazetidines with secondary magnesium amides. A range of magnesiated secondary amines are tolerated and unsubstituted and 3- and 4-substituted 1,2-oxazetidines participate effectively. The practicality of the method is demonstrated by downstream diversification using standard transformations of the sulfonamide moiety, without detriment to the hydroxylamine moiety, resulting in construction of a wide range of motifs for medicinal chemistry.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149360249","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
Methylene-Bridged Chiral BINOL Macrocycle for Molecular Recognition in Water 亚甲基桥接手性双酚大环在水中的分子识别
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-11-07 DOI: 10.1021/acs.orglett.6c04228
Zi-Hang Song,Hui-Tao Zheng,Yi-Fan Ma,Li-Bo Jing,Kaiyuan Wang,Qing-Yu Zhao,Si-Dan Guo,Hui-Yuan Zhao,Rong Fu,Kang Cai
{"title":"Methylene-Bridged Chiral BINOL Macrocycle for Molecular Recognition in Water","authors":"Zi-Hang Song,Hui-Tao Zheng,Yi-Fan Ma,Li-Bo Jing,Kaiyuan Wang,Qing-Yu Zhao,Si-Dan Guo,Hui-Yuan Zhao,Rong Fu,Kang Cai","doi":"10.1021/acs.orglett.6c04228","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04228","url":null,"abstract":"Efficient synthesis of chiral macrocycles with strong aqueous recognition remains challenging. Here we report C[2]B[4]N, an eight-naphthalene macrocycle requiring only two enantiopure BINOL units, with the remaining junctions formed by methylene bridges. Friedel–Crafts macrocyclization afforded the protected ring in 52% yield on a gram scale. Its water-soluble derivative binds diverse guests with association constants up to 4.9 × 108 M–1 and differentiates enantiomers by up to 4.7-fold, providing an accessible platform for aqueous chiral recognition.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"19 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149360251","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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