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"Green" Oxidant (Oxygen) Mediated Synthesis of N-(2-(Methylsulfonyl)ethyl)amide Derivatives Using DMSO as a Dual Synthon and Solvent. “绿色”氧化剂（氧）介导合成N-（2-（甲基磺酰基）乙基）酰胺衍生物的DMSO作为双合成物和溶剂。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-10-01 DOI: 10.1021/acs.orglett.5c03851
Yongfa Xie,Changlong Zhuo,Siming Gong,Hui Wu,Hu Cai
{"title":"\"Green\" Oxidant (Oxygen) Mediated Synthesis of N-(2-(Methylsulfonyl)ethyl)amide Derivatives Using DMSO as a Dual Synthon and Solvent.","authors":"Yongfa Xie,Changlong Zhuo,Siming Gong,Hui Wu,Hu Cai","doi":"10.1021/acs.orglett.5c03851","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03851","url":null,"abstract":"Sulfone derivatives are important components of many pharmaceuticals. This Letter reports an efficient method for synthesizing N-(2-(methylsulfonyl)ethyl)amide compounds with sulfone skeletons from amide compounds and dimethyl sulfoxide (DMSO) using an environmentally benign oxidant (oxygen). This metal-free protocol features operational simplicity, a low-cost and nonhazardous oxidant mediator, good functional group tolerance, and scalability to gram-scale. Notably, DMSO acts as a dual synthon donor, providing both methylene (-CH2-) and methylsulfonyl (-SO2Me) groups to form C(sp3)-N and C(sp3)-C(sp3) bonds while serving as the solvent. A radical mechanism is proposed based on control experiments and EPR spectroscopy.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"114 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145203803","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
Optimized and Scalable Synthesis of BOPYRENPY Chromophores: Access to a Seven-Membered BF2-C60 Dyad for Reactive Oxygen Species Generation. BOPYRENPY发色团的优化和可扩展合成：用于活性氧生成的七元BF2-C60二偶体的获取
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-10-01 DOI: 10.1021/acs.orglett.5c03720
Edwin J Gonzalez Lopez,Claudia Chávez Hernández,Sofia Santamarina,Daniel A Heredia
{"title":"Optimized and Scalable Synthesis of BOPYRENPY Chromophores: Access to a Seven-Membered BF2-C60 Dyad for Reactive Oxygen Species Generation.","authors":"Edwin J Gonzalez Lopez,Claudia Chávez Hernández,Sofia Santamarina,Daniel A Heredia","doi":"10.1021/acs.orglett.5c03720","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03720","url":null,"abstract":"We report an optimized and scalable synthesis of BOPYRENPY, a seven-membered BF2-chelated chromophore, improving yields from 10% to almost 90%, on a multigram scale via acetonitrile-mediated stabilization of BF3 intermediates. This approach enabled the first covalently linked seven-membered BF2-C60 dyad, previously inaccessible due to low precursor availability. Optical and electrochemical studies demonstrate efficient intramolecular energy and electron transfer to the fullerene triplet state, driving the generation of reactive oxygen species (ROS) and establishing a new heavy-atom-free triplet photosensitizer platform for ROS-mediated applications.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"35 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145195125","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
Generation [via Tetradehydro-Diels-Alder Reactions] and Reactivity of 6-Fluorocyclohexa-1,2,4-triene Intermediates. 6-氟环己-1,2,4-三烯中间体的生成[通过四氢- diels - alder反应]和反应性。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-10-01 DOI: 10.1021/acs.orglett.5c03636
Paul V Kevorkian,Thomas R Hoye
{"title":"Generation [via Tetradehydro-Diels-Alder Reactions] and Reactivity of 6-Fluorocyclohexa-1,2,4-triene Intermediates.","authors":"Paul V Kevorkian,Thomas R Hoye","doi":"10.1021/acs.orglett.5c03636","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03636","url":null,"abstract":"We report the engagement of the 2,6-difluorophenyl substituent in tetradehydro-Diels-Alder (TDDA) reactions. The use of fluorine was guided by DFT computations. Acceleration of TDDA cycloisomerization by an anhydride linker in the substrates was also key. Trapping of the strained cyclic allene intermediate by nucleophilic carbons in external heterocycles, an enol, and alkenes led to unusual reactivities (e.g., one rationalized by rearrangement to a carbene intermediate).","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"17 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145195121","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
Biomimetic Total Synthesis of (±)-Lappaceolides A and B. （±）-拉帕内酯A和B的仿生全合成。
IF 5 1区 化学
Organic Letters Pub Date : 2025-10-01 DOI: 10.1021/acs.orglett.5c02445
Rajanish R Pallerla, Jenna Hakola, Leevi Härkönen, Juha H Siitonen
{"title":"Biomimetic Total Synthesis of (±)-Lappaceolides A and B.","authors":"Rajanish R Pallerla, Jenna Hakola, Leevi Härkönen, Juha H Siitonen","doi":"10.1021/acs.orglett.5c02445","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c02445","url":null,"abstract":"<p><p>The first total synthesis of lappaceolides A and B is achieved in two steps by using a biomimetic vinylogous-Michael-oxa-Michael domino reaction. The domino reaction proceeds with Cs<sub>2</sub>CO<sub>3</sub> in 1,2-DCE at elevated temperatures and requires careful kinetic control. The total synthesis provides further proof of the biosynthetic hypothesis of lappaceolides being dimers of the natural product siphonodin.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":5.0,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145205215","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
Ruthenium-Catalyzed Selective C4 C-H Phosphorylation of Indoles and Mechanistic Insights. 钌催化吲哚选择性C4 C-H磷酸化及其机理研究。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-10-01 DOI: 10.1021/acs.orglett.5c02331
Xue-Ya Gou,Yuan-Xin Zhi,Cui-Tian Wang,Yang Lei,Li Zhao,Bo-Sheng Zhang,Yong-Min Liang
{"title":"Ruthenium-Catalyzed Selective C4 C-H Phosphorylation of Indoles and Mechanistic Insights.","authors":"Xue-Ya Gou,Yuan-Xin Zhi,Cui-Tian Wang,Yang Lei,Li Zhao,Bo-Sheng Zhang,Yong-Min Liang","doi":"10.1021/acs.orglett.5c02331","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c02331","url":null,"abstract":"Phosphorylated indoles are valuable motifs in medicinal chemistry and functional materials, attracting considerable attention for their efficient and selective synthesis. We report the first ruthenium-catalyzed direct C-H phosphorylation at C4 of indoles, without preprotection of C2 and C3. This strategy enables the efficient construction of structurally diverse phosphorylated indole derivatives and delivers N-H-free phosphorylated indoles in high yields via a one-pot deprotection sequence. Density functional theory (DFT) studies revealed that steric effects from bulky N-substituents are the key driving force for C4 selectivity, effectively suppressing competing activation pathways at C2 and C3 and thus enabling excellent regioselective control.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"126 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145203800","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
Exploring Pd-Catalyzed Hydrocarbation of Allenes: Focusing on Propa-1,2-diene for the Isopropenylation of C(sp2) Halides. 探索pd催化的烯类加氢反应：以丙二烯-1,2-二烯为重点的C（sp2）卤化物异丙烯化反应。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-30 DOI: 10.1021/acs.orglett.5c03623
Louis Perrault,Romain Magny,Lucas Pagès,Rayane Mekerri,Clément Burgevin,Damien Cordeau,Emmanuel Roulland
{"title":"Exploring Pd-Catalyzed Hydrocarbation of Allenes: Focusing on Propa-1,2-diene for the Isopropenylation of C(sp2) Halides.","authors":"Louis Perrault,Romain Magny,Lucas Pagès,Rayane Mekerri,Clément Burgevin,Damien Cordeau,Emmanuel Roulland","doi":"10.1021/acs.orglett.5c03623","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03623","url":null,"abstract":"The operatively simple Pd-catalyzed allene hydrocarbation described here uses HCO2Na and produces innocuous CO2 and sodium halide, and pure coupling products are isolated via water/ether extraction in most cases. This new transformation displays a broad C(sp2) halide scope, functional group tolerance, and good to excellent yields and allows inexpensive selective deuteration. Pd loadings of 0.10 mol % remain effective, and gram-scale reactions were conducted. The protocol extends to O-, N-, Si-, and C-substituted allenes, demonstrating its versatility.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"34 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145194624","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
Sc(III)-Catalyzed Carbonyl-Yne Reaction for the Diastereoselective Allene Synthesis: A Concerted Asynchronous Mechanism. Sc（III）催化羰基-炔反应合成非对映选择性烯：协同异步机制。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-30 DOI: 10.1021/acs.orglett.5c03172
Xinya Yuan,Jiashen Yang,Shaozhong Wang
{"title":"Sc(III)-Catalyzed Carbonyl-Yne Reaction for the Diastereoselective Allene Synthesis: A Concerted Asynchronous Mechanism.","authors":"Xinya Yuan,Jiashen Yang,Shaozhong Wang","doi":"10.1021/acs.orglett.5c03172","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03172","url":null,"abstract":"The carbonyl-yne reaction, involving propargylic C-H bond cleavage for carbon-carbon bond formation, is significantly less developed than the classical Alder-ene reaction due to the linear geometry and relatively weak nucleophilicity of alkynes compared to alkenes. Herein, we report a Sc(OTf)3-catalyzed carbonyl-yne reaction enabling the diastereoselective synthesis of multisubstituted allenes from α-ketoamide-tethered alkynes with 100% atom economy and excellent diastereoselectivity (up to 20/1 dr). DFT calculations support a concerted, asynchronous mechanism involving C-C bond formation and propargylic C-H cleavage. Theoretical analysis suggests that the observed stereoselectivity arises from an interplay of electronic and entropic effects in the transition states.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"75 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145189235","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
Chlorobactine A, a Dimeric Dichlorated Metabolite from Marine-Derived Streptomyces thermolineatus NAK03196. 海洋源热链霉菌NAK03196的二聚二氯代谢物氯巴碱A。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-30 DOI: 10.1021/acs.orglett.5c03588
Guodong Zhang,Jing Shi,Chao Zhang,Wen Wang,Xiao Yang,Zijun Xiong,Shuai Ma,Rong Wang,Zhikai Guo,Ruihua Jiao
{"title":"Chlorobactine A, a Dimeric Dichlorated Metabolite from Marine-Derived Streptomyces thermolineatus NAK03196.","authors":"Guodong Zhang,Jing Shi,Chao Zhang,Wen Wang,Xiao Yang,Zijun Xiong,Shuai Ma,Rong Wang,Zhikai Guo,Ruihua Jiao","doi":"10.1021/acs.orglett.5c03588","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03588","url":null,"abstract":"Using the one strain many compounds (OSMAC) strategy and guided by LC-MS results, we explored the metabolites of marine algae-derived strain Streptomyces thermolineatus NAK03196 and discovered a new class of molecules with an unexpected skeleton, chlorobactine A (1). Its structure was determined by 1D and 2D NMR spectroscopy, HR-ESI-MS, single-crystal X-ray diffraction analysis (Cu Kα), and ECD calculation. Chlorobactine A (1) contains dichlorine atoms and possesses a unique [6/6/6] tricyclic fused skeleton structure. Meanwhile, a plausible biosynthetic pathway for 1 was proposed based on the molecular structures and bioinformatic analysis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"19 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145189445","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
Organophotoredox Dioxygenation of Alkenes via ROH···F-Activated N-Alkoxyphthalimides. 通过ROH··f活化的n -烷氧基邻苯二胺进行烯烃的有机光氧化还原双氧合。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-30 DOI: 10.1021/acs.orglett.5c03734
Pau Sarró,Albert Gallego-Gamo,Elies Molins,Roser Pleixats,Carolina Gimbert-Suriñach,Adelina Vallribera,Albert Granados
{"title":"Organophotoredox Dioxygenation of Alkenes via ROH···F-Activated N-Alkoxyphthalimides.","authors":"Pau Sarró,Albert Gallego-Gamo,Elies Molins,Roser Pleixats,Carolina Gimbert-Suriñach,Adelina Vallribera,Albert Granados","doi":"10.1021/acs.orglett.5c03734","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03734","url":null,"abstract":"The generation and controlled reactivity of alkoxyl radicals remain challenging due to their high energy and tendency for β-scission or hydrogen atom transfer events. Herein, we report a photoredox-catalyzed dioxygenation of alkenes enabled by the activation of fluorinated N-alkoxyphthalimides through hydrogen-bonded aggregates with ROH···F. This transformation proceeds under mild, metal-free conditions using an organophotocatalyst and a simple alcohol, affording a diverse range of dialkoxylated products with high functional group tolerance and good scalability. Mechanistic studies─including UV-Vis spectroscopy, NMR, cyclic voltammetry, and Stern-Volmer quenching─reveal a radical/polar crossover pathway.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"34 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145194611","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-Excited Lewis Acid Catalyzed Intermolecular [2σ + 3π] Photocycloadditions. 可见光激发路易斯酸催化分子间[2σ + 3π]光环加成。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-30 DOI: 10.1021/acs.orglett.5c03637
Tianlei Du,Yunzhi Xie,Qiujie Qin,Kun Yin,Jian Li,Xinyao Li,Zijun Zhou
{"title":"Visible-Light-Excited Lewis Acid Catalyzed Intermolecular [2σ + 3π] Photocycloadditions.","authors":"Tianlei Du,Yunzhi Xie,Qiujie Qin,Kun Yin,Jian Li,Xinyao Li,Zijun Zhou","doi":"10.1021/acs.orglett.5c03637","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03637","url":null,"abstract":"Herein, we introduce an innovative approach employing a direct visible-light-excited Lewis acid-catalyzed [2σ + 3π] cycloaddition reaction between bicyclo[1.1.0]butanes and α-vinyl azides via diradical intermediate. This transformation proceeds efficiently in the absence of any external photocatalyst produces versatile 2-azabicyclo[3.1.1]heptene derivatives with a broad substrate scope, achieving yields of up to 94% across 34 examples. The synthetic practicality was further demonstrated through a scaled-up reaction, and the transformation of the imidazole auxiliary into an ester group.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"18 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145189234","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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