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β-CF3 Alkynones for Amine Conjugation under Aqueous Conditions β-CF3炔酮在水溶液条件下的氨基偶联
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-07 DOI: 10.1021/acs.orglett.6c03805
Fanyi Hou, Jinzan Feng, Teck-Peng Loh, Yue Wang
{"title":"β-CF3 Alkynones for Amine Conjugation under Aqueous Conditions","authors":"Fanyi Hou,&nbsp;Jinzan Feng,&nbsp;Teck-Peng Loh,&nbsp;Yue Wang","doi":"10.1021/acs.orglett.6c03805","DOIUrl":"10.1021/acs.orglett.6c03805","url":null,"abstract":"<p>We report an aqueous conjugate addition of primary andsecondaryamines to β-CF<sub>3</sub> alkynones under mild conditions withoutadded metal catalysts or activating reagents. This protocol affordsstable, CF<sub>3</sub>-containing enaminone conjugates in phosphatebuffer and is applicable to structurally diverse amine substrates.Its utility is demonstrated by the modification of drugs, amino acidesters, dipeptides, complex bioactive peptides, and proteins, as wellas two-step fluorescent labeling of lysozyme confirmed by fluorescenceSDS–PAGE analysis.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"12971–12976"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088578","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
Ligand Accelerated Palladium-Catalyzed C–H Arylation of Electron-Deficient Polyfluoroarenes with Aryl Bromides 配体加速钯催化的缺电子多氟芳烃与芳基溴的C-HArylation反应
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-06 DOI: 10.1021/acs.orglett.6c03763
Srinivasarao Tenneti, Nageswara Rao Kalikinidi, Arun D. R. Shada, Srinivasrao Ganipisetti, Jonathan Bietsch, Venkatarathnam Nasipireddy, Madhusudhan Gadi, Annada Maity, Sailu Munnuri, Shanika M. P. Gamage, Santhosh Reddy Naini, Sameera S. Arachchige, Praveen Gajula, Rajasekar Reddy Annapureddy, Lalith P. Samankumara, Lalitha Gummidi, Sridhar Regati, Rahul Dilip Shingare, Badrinath Kakde, Mohammed Sharique, Jonathan Gordon, Virendra Tiwari, Sudhakar Guvvala, Omkar Revu, Chetan Joshi, Anji Chen, Venkata Surya Kumar Choutipalli, Venkatesan Subramanian, Gopal Sirasani, Rajender Reddy Leleti, Bo Qu, Chris H. Senanayake
{"title":"Ligand Accelerated Palladium-Catalyzed C–H Arylation of Electron-Deficient Polyfluoroarenes with Aryl Bromides","authors":"Srinivasarao Tenneti,&nbsp;Nageswara Rao Kalikinidi,&nbsp;Arun D. R. Shada,&nbsp;Srinivasrao Ganipisetti,&nbsp;Jonathan Bietsch,&nbsp;Venkatarathnam Nasipireddy,&nbsp;Madhusudhan Gadi,&nbsp;Annada Maity,&nbsp;Sailu Munnuri,&nbsp;Shanika M. P. Gamage,&nbsp;Santhosh Reddy Naini,&nbsp;Sameera S. Arachchige,&nbsp;Praveen Gajula,&nbsp;Rajasekar Reddy Annapureddy,&nbsp;Lalith P. Samankumara,&nbsp;Lalitha Gummidi,&nbsp;Sridhar Regati,&nbsp;Rahul Dilip Shingare,&nbsp;Badrinath Kakde,&nbsp;Mohammed Sharique,&nbsp;Jonathan Gordon,&nbsp;Virendra Tiwari,&nbsp;Sudhakar Guvvala,&nbsp;Omkar Revu,&nbsp;Chetan Joshi,&nbsp;Anji Chen,&nbsp;Venkata Surya Kumar Choutipalli,&nbsp;Venkatesan Subramanian,&nbsp;Gopal Sirasani,&nbsp;Rajender Reddy Leleti,&nbsp;Bo Qu,&nbsp;Chris H. Senanayake","doi":"10.1021/acs.orglett.6c03763","DOIUrl":"10.1021/acs.orglett.6c03763","url":null,"abstract":"<p>A ligandaccelerated highly efficient palladium-catalyzed C–Harylation of electron-deficient polyfluoroarenes with aryl and heteroarylbromides has been developed. The reaction proceeds efficiently undermild conditions with low catalyst loading (0.25 mol % Pd) and ligandloading (0.275 mol %), affording a broad range of fluorinated biarylproducts in good to excellent yields. The methodology exhibits a widesubstrate scope and good functional group tolerance. Its syntheticutility is demonstrated through the concise synthesis of several industriallyrelevant molecules, highlighting the practicality, efficiency, andscalability of the catalytic system.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"12959–12964"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088584","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
Energy Transfer-Mediated Carboamination of Alkenes to Access γ-Amino-1,3-dicarbonyl Scaffolds 能量转移介导烯基碳胺化以获得γ-氨基-1,3-二羰基支架
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-05 DOI: 10.1021/acs.orglett.6c04244
Cong Huang, Qian Zhang, Mei Xiang, Jie Gao, Kai Chen, Yu Zheng, Hua Yang
{"title":"Energy Transfer-Mediated Carboamination of Alkenes to Access γ-Amino-1,3-dicarbonyl Scaffolds","authors":"Cong Huang,&nbsp;Qian Zhang,&nbsp;Mei Xiang,&nbsp;Jie Gao,&nbsp;Kai Chen,&nbsp;Yu Zheng,&nbsp;Hua Yang","doi":"10.1021/acs.orglett.6c04244","DOIUrl":"10.1021/acs.orglett.6c04244","url":null,"abstract":"<p>A visible light-induced, energy transfer-mediated strategyforthe carboamination of alkenes was developed using a rationally designedenyl oxime ester-based bifunctional reagent, enabling the efficientconstruction of structurally diverse γ-amino-1,3-dicarbonylcompounds. The novel bifunctional reagent can be facilely preparedfrom readily available feedstock chemicals, and the rationale of thisstructural design relies on the resonance-driven spin center shift(SCS) to generate the key carbon-centered radical. A wide range ofalkenes participated in this transformation smoothly, affording thedesired products in moderate to good yields with excellent functionalgroup tolerance and high regioselectivity (&gt;20:1). This work notonlyprovides a new strategy for the efficient construction of γ-amino-1,3-dicarbonylscaffolds but also demonstrates the potential of innovative bifunctionalreagent design in expanding the synthetic utility of energy transfercatalysis.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"13123–13128"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088724","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
Thermally Stable Energetic Salts Featuring Tetrazine-Derived Diammonium Cations and Nitrogen-Rich Energetic Anions 含四氮衍生二铵阳离子和富氮阴离子的热稳定能盐
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-01 DOI: 10.1021/acs.orglett.6c03422
Meera Khatri, Priyanka Das, Amit Bijlwan, Dheeraj Kumar
{"title":"Thermally Stable Energetic Salts Featuring Tetrazine-Derived Diammonium Cations and Nitrogen-Rich Energetic Anions","authors":"Meera Khatri,&nbsp;Priyanka Das,&nbsp;Amit Bijlwan,&nbsp;Dheeraj Kumar","doi":"10.1021/acs.orglett.6c03422","DOIUrl":"10.1021/acs.orglett.6c03422","url":null,"abstract":"<p>A nitrogen-rich tetrazine-based dicationicprecursor,(1,2,4,5-tetrazine-3,6-diyl)dimethanaminiumchloride (<strong>3</strong>), was synthesized in an efficient three-stepprocedure from readily available starting materials. Subsequent pairingof <strong>3</strong> with a series of nitrogen- and oxygen-rich energeticanions afforded energetic salts (<strong>4</strong>–<strong>12</strong>) that exhibit high detonation performance, good thermal stability,and reduced mechanical sensitivity. Among all the compounds, <strong>9</strong> exhibited the most favorable balance between energetic performance(V<sub>d</sub> = 8533 m s<sup>–1</sup>; P = 27.09 GPa) andstability (<em>T</em><sub>d</sub> = 207 °C; IS = 12.5J), with energetic performance comparable to that of the well-knownexplosive RDX. Overall, these results demonstrate that tetrazine-deriveddiamine cations provide a promising platform for the development ofthermally stable energetic salts with balanced energetic performanceand stability.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"12873–12877"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088728","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
Meta-Selective Phenylselenylation of Pyridines through Oxazino Azines 吡啶通过恶氮杂氮的间选择性苯硒化反应
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-01 DOI: 10.1021/acs.orglett.6c03584
Huiqiang Li, Wenxia Hu, Dongxu Xie, Haihan Yu, Mingzhong Yang, Tao Li, Ruoyi Hou, Ganyu Cong, Hongbin Zhang, E Tang
{"title":"Meta-Selective Phenylselenylation of Pyridines through Oxazino Azines","authors":"Huiqiang Li,&nbsp;Wenxia Hu,&nbsp;Dongxu Xie,&nbsp;Haihan Yu,&nbsp;Mingzhong Yang,&nbsp;Tao Li,&nbsp;Ruoyi Hou,&nbsp;Ganyu Cong,&nbsp;Hongbin Zhang,&nbsp;E Tang","doi":"10.1021/acs.orglett.6c03584","DOIUrl":"10.1021/acs.orglett.6c03584","url":null,"abstract":"<p>A metal-free and TCCA-promoted highly regioselective <em>meta</em>-C–H bond phenylselenylation of pyridines usingbench-stabledearomatized oxazino azines has been developed. A substantial varietyof 3-(phenylselanyl)pyridines were obtained under open-air and mildconditions, with a maximum yield of 90%. The scalable process wasalso available from pyridine directly in a “one-pot”version and was used in the late-stage <em>meta</em>-phenylselenylationof pyridine-containing drugs and natural product derivatives, providingan efficient platform for diverse <em>meta</em>-selectiveselenylfunctionalization of pyridine frameworks.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"12898–12902"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088067","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
Electrochemical Divergent Transformation of Flavonoids to Dihydroflavonols and 3-Iodoflavones 类黄酮的电化学分化转化为二氢黄酮醇和3-碘黄酮
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-09-30 DOI: 10.1021/acs.orglett.6c03424
Yi Sun, Changsheng Qin, Xinyue Li, Jiawei Guo, Zhihua Zhang, Jingfang Wang, Chenxu Li, Jierong Liu, Lanyu Yang, Shoucai Wang, Fanghua Ji, Guangbin Jiang
{"title":"Electrochemical Divergent Transformation of Flavonoids to Dihydroflavonols and 3-Iodoflavones","authors":"Yi Sun,&nbsp;Changsheng Qin,&nbsp;Xinyue Li,&nbsp;Jiawei Guo,&nbsp;Zhihua Zhang,&nbsp;Jingfang Wang,&nbsp;Chenxu Li,&nbsp;Jierong Liu,&nbsp;Lanyu Yang,&nbsp;Shoucai Wang,&nbsp;Fanghua Ji,&nbsp;Guangbin Jiang","doi":"10.1021/acs.orglett.6c03424","DOIUrl":"10.1021/acs.orglett.6c03424","url":null,"abstract":"<p>We report an electrochemically regulated divergent C–Hfunctionalizationof flavonoids that enables the controllable synthesis of dihydroflavonolsor 3-iodoflavones from the same substrates by simply switching theelectrolyte and solvent. This protocol operates in an undivided cellat room temperature under air, featuring tunable selectivity, no needfor external oxidants or transition-metal catalysts, and operationalsimplicity. Mechanistic studies identify the key reaction intermediates.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"12884–12890"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088160","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
Reversible Oxidation of a Nonathia[42]Nonaphyrin(1.1.0.1.1.0.1.1.0) to a 40π Dication Diradicaloid Nonathia[42]Nonaphyrin（1.1.0.1.1.0.1.1.0）可逆氧化为40π二根碱
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-06 DOI: 10.1021/acs.orglett.6c02255
Nikita Panchmukhi, Hosahalli S. Udaya, Swati Deswal, Pragati Shukla, Vasudha Sharma, Vijaya Thangaraj, Bapan Jana, Supriyo Santra, Debashree Ghosh, Maheswaran Shanmugam, Venkataramanarao G. Anand
{"title":"Reversible Oxidation of a Nonathia[42]Nonaphyrin(1.1.0.1.1.0.1.1.0) to a 40π Dication Diradicaloid","authors":"Nikita Panchmukhi,&nbsp;Hosahalli S. Udaya,&nbsp;Swati Deswal,&nbsp;Pragati Shukla,&nbsp;Vasudha Sharma,&nbsp;Vijaya Thangaraj,&nbsp;Bapan Jana,&nbsp;Supriyo Santra,&nbsp;Debashree Ghosh,&nbsp;Maheswaran Shanmugam,&nbsp;Venkataramanarao G. Anand","doi":"10.1021/acs.orglett.6c02255","DOIUrl":"10.1021/acs.orglett.6c02255","url":null,"abstract":"<p>A one-pot condensation of bithiophene with thiophenediol underacidic conditions yields 28π, 42π, and 56π expandedporphyrinoids. X-ray crystallographic studies revealed a planar topologyfor both 28π and 42π macrocycles. Spectroscopic and quantumchemical calculations reveal weak ring current effects, while theyundergo reversible two-electron ring oxidation as confirmed by electrochemicalstudies. Spectroscopic and quantum chemical calculations support adiradicaloid character for the 40π dicationic species.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"12849–12853"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088576","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
Alkoxy Radical-Mediated Alkene Difunctionalization via Electrophotochemical LMCT Catalysis for the Synthesis of Functionalized Ethers 电光化学LMCT催化合成功能化醚的烷氧基自由基介导烯烃双官能化研究
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-06 DOI: 10.1021/acs.orglett.6c03725
Caolin Wang, Jianxin Huang, Jianye Zhang, Ting Wang, Chun Cheng, Xiaorong Yang
{"title":"Alkoxy Radical-Mediated Alkene Difunctionalization via Electrophotochemical LMCT Catalysis for the Synthesis of Functionalized Ethers","authors":"Caolin Wang,&nbsp;Jianxin Huang,&nbsp;Jianye Zhang,&nbsp;Ting Wang,&nbsp;Chun Cheng,&nbsp;Xiaorong Yang","doi":"10.1021/acs.orglett.6c03725","DOIUrl":"10.1021/acs.orglett.6c03725","url":null,"abstract":"<p>Alkoxy radical-mediated hydroetherification offers anatom-economicalapproach for C–O bond construction. However, the difunctionalizationof alkenes driven by alkoxy radicals remains elusive due to the inherentchallenges associated with the generation and controlled reactivityof these reactive oxygen-centered radicals. Here we report a homogeneousmolecular electrophotochemical LMCT catalysis strategy that enablesthe difunctionalization of enol derivatives, achieving efficient alkenyletherificationto access a diverse array of functionalized ethers. This method featuresmild conditions, broad substrate scope encompassing both electron-richand electron-deficient alkenes, and effective suppression of directalkene oxidation side reactions. Detailed mechanistic studies revealthat a visible-light-induced ligand-to-metal charge transfer (LMCT)process selectively activates the alcohol hydroxyl group, generatinga highly electrophilic alkoxy radical in situ to initiate the anti-Markovnikovintramolecular addition to the alkene. Subsequent electrochemicaloxidation precisely dictates the fate of the resulting carbon-centeredradical, enabling the introduction of an alkenyl group, respectively,to ultimately yield the target products.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"12941–12946"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088583","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
Insertion into Donor–Acceptor Cyclopropanes with Carbon–Sulfur Moieties Derived from Sulfoxonium Ylides and Elemental Sulfur 从亚砜基脲和单质硫衍生的碳-硫基团插入供体-受体环丙烷
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-05 DOI: 10.1021/acs.orglett.6c04002
Vu H. Luu, Dat H. Tran, Tien V. Le, Hoang V. M. Trinh, Khanh T. N. Ong, Anh T. Nguyen, Tung T. Nguyen
{"title":"Insertion into Donor–Acceptor Cyclopropanes with Carbon–Sulfur Moieties Derived from Sulfoxonium Ylides and Elemental Sulfur","authors":"Vu H. Luu,&nbsp;Dat H. Tran,&nbsp;Tien V. Le,&nbsp;Hoang V. M. Trinh,&nbsp;Khanh T. N. Ong,&nbsp;Anh T. Nguyen,&nbsp;Tung T. Nguyen","doi":"10.1021/acs.orglett.6c04002","DOIUrl":"10.1021/acs.orglett.6c04002","url":null,"abstract":"<p>The(3 + 2) cycloaddition of donor–acceptor cyclopropanes(DACs) with carbon–sulfur 2π components has become anemerging method to rapidly assemble tetrahydrothiophenes. Startingmaterials donating the carbon–sulfur unit are often isolatedfrom thionation of carbonyls or carboxylic acid derivatives. Hereinwe report a method for the cycloaddition of DACs with carbon–sulfurmoieties presumably formed <em>in situ</em> via β-sulfurationof α-carbonyl sulfoxonium ylides with elemental sulfur. Theinsertion occurred without the assistance of Lewis acid, perhaps dueto the strongly polarized carbon–sulfur-containing intermediate.The hitherto challenging α-monosubstituted tetrahydrothiopheneswere obtained with a wide range of tolerated functionalities.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"13094–13097"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088623","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
One-Pot TandemAnnulation of N -(2-Alkynylaryl)- N -sulfonylcyanamides with Water for the Synthesisof 2-Amino-3-carbonylindoles N -（2-炔芳基）- N -磺酰氰酰胺与水的一锅反应合成2-氨基-3-羰基lindoles
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-16 DOI: 10.1021/acs.orglett.6c03880
Yijie Wang,Tong Lu,Yu Li,Xiao-Na Wang
{"title":"One-Pot Tandem\u0000Annulation of\u0000 N\u0000 -(2-Alkynylaryl)-\u0000 N\u0000 -sulfonylcyanamides with Water for the Synthesis\u0000of 2-Amino-3-carbonylindoles","authors":"Yijie Wang,Tong Lu,Yu Li,Xiao-Na Wang","doi":"10.1021/acs.orglett.6c03880","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03880","url":null,"abstract":"Abstract A metal-free, one-pot tandem annulation of N-(2-alkynylaryl)-N-sulfonylcyanamides with water has been developed for synthesizing 2-amino-3-carbonylindoles. The reaction proceeds via isolable N,O-BF2-chelated intermediates, which undergo Et3N-mediated ring opening. Water serves as the carbonyl oxygen source, as supported by anhydrous control and H218O-labeling experiments. The protocol tolerates diverse sulfonamide groups and substituents, enables gram-scale synthesis, and allows for subsequent deprotection.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209512","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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