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Dual Activation of Organoboron for the Ion-Pair-Mediated Synthesis of Hindered Alkyl Fluorides 离子对介导的受阻氟烷基化合物合成中有机硼的双重活化
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-24 DOI: 10.1021/acs.orglett.5c01127
Soo Young Kim, Juho Lee, Won Seok Ham, Tae Yeong Im, Su Yong Go, Hong Geun Lee
{"title":"Dual Activation of Organoboron for the Ion-Pair-Mediated Synthesis of Hindered Alkyl Fluorides","authors":"Soo Young Kim, Juho Lee, Won Seok Ham, Tae Yeong Im, Su Yong Go, Hong Geun Lee","doi":"10.1021/acs.orglett.5c01127","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01127","url":null,"abstract":"A novel electrochemical approach for the synthesis of hindered alkyl fluorides has been developed. The protocol grants access to a diverse array of tertiary and secondary alkyl fluorides using readily attainable organoboron precursors under mild conditions. The efficiency of the system stems from the dual activation of the redox-active borate intermediate, providing both electrophilic and nucleophilic reaction partners in the form of an internally generated ion pair.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"32 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143867168","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
Multi-Auto-Tandem Reaction to Access Site-Specific Functionalized Tricyclic Furo[3,2-c]coumarins and Naphtho[2,3-b]furan-4,9-diones 多自串联反应获取位点特异性功能化三环呋喃[3,2-c]香豆素和萘[2,3-b]呋喃-4,9-二酮
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-04-24 DOI: 10.1021/acs.orglett.5c0081110.1021/acs.orglett.5c00811
Xiang Liu*, Hexiang Wang, Dongrong Lin, Zhen Lin, Qiye Chen, Baofu Zhu and Hua Cao*, 
{"title":"Multi-Auto-Tandem Reaction to Access Site-Specific Functionalized Tricyclic Furo[3,2-c]coumarins and Naphtho[2,3-b]furan-4,9-diones","authors":"Xiang Liu*,&nbsp;Hexiang Wang,&nbsp;Dongrong Lin,&nbsp;Zhen Lin,&nbsp;Qiye Chen,&nbsp;Baofu Zhu and Hua Cao*,&nbsp;","doi":"10.1021/acs.orglett.5c0081110.1021/acs.orglett.5c00811","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00811https://doi.org/10.1021/acs.orglett.5c00811","url":null,"abstract":"<p >A three-component multi-auto-tandem reaction for the construction of site-specific tricyclic furo[3,2-<i>c</i>]coumarins via the formation of C–C, C–O, and C–S bonds in one step from 4-hydroxycoumarins/4-hydroxy-2-pyrones, ynals, and sodium sulfinates is reported. This cascade reaction efficiently produces a variety of rare C-2-functionalized furo[3,2-<i>c</i>]coumarins in moderate to good yields under straightforward reaction conditions. Furthermore, this protocol can be extended to a three-component coupling involving 2-hydroxy-1,4-naphthoquinone, ynals, and sodium sulfinates, yielding tricyclic naphtho[2,3-<i>b</i>]furan-4,9-dione derivatives. Notably, the carbonyl group and the α-position of ynals act as C-2 synthons in the specific multi-auto-tandem reaction, enabling the two aforementioned types of multicomponent transformations.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 17","pages":"4445–4449 4445–4449"},"PeriodicalIF":4.9,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894072","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
Construction of 3-Hydroxyindolin-2-ones via Ru(II)-Catalyzed Domino Alkylation/Cyclization/Oxidation of 2-Aminophenethanols Ru（II）催化2-氨基酚醇的多米诺烷基化/环化/氧化法制备3-羟基吲哚-2-酮
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-24 DOI: 10.1021/acs.orglett.5c01063
Chuanhu Wang, Jingwen Huang, Bo Deng, Wei Sun, Tongyu Xu, Fanlong Zeng
{"title":"Construction of 3-Hydroxyindolin-2-ones via Ru(II)-Catalyzed Domino Alkylation/Cyclization/Oxidation of 2-Aminophenethanols","authors":"Chuanhu Wang, Jingwen Huang, Bo Deng, Wei Sun, Tongyu Xu, Fanlong Zeng","doi":"10.1021/acs.orglett.5c01063","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01063","url":null,"abstract":"A novel Ru(II)-catalyzed domino reaction, comprising alkylation, cyclization, and oxidation of 2-aminophenethanols with benzyl alcohols, has been developed for the synthesis of 3-hydroxyindolin-2-ones. This transformation exhibits excellent synthetic efficiency, enabling the selective formation of four or three σ bonds, one π bond, and one quaternary carbon center in one step under identical conditions. Furthermore, it provides a versatile approach to 3-hydroxyindolin-2-one frameworks with distinct substituents at the 1- and 3-positions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"42 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872848","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
A General Direct Aldehyde C–H Alkylation via TBADT-Nickel Synergistic Catalysis tbadt -镍协同催化的乙醛C-H直接烷基化研究
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-24 DOI: 10.1021/acs.orglett.5c00949
Zhimin Hu, Ji-Wei Sang, Shize Xie, Yujia Song, Qiuhao Li, Bing Wang, Zheng-Yang Xu, Yu Zhang, Runhui Liu, Wei-Dong Zhang, Jinxin Wang
{"title":"A General Direct Aldehyde C–H Alkylation via TBADT-Nickel Synergistic Catalysis","authors":"Zhimin Hu, Ji-Wei Sang, Shize Xie, Yujia Song, Qiuhao Li, Bing Wang, Zheng-Yang Xu, Yu Zhang, Runhui Liu, Wei-Dong Zhang, Jinxin Wang","doi":"10.1021/acs.orglett.5c00949","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00949","url":null,"abstract":"Herein, we present a nickel/tetrabutylammonium decatungstate (TBADT)-catalyzed protocol for general C–H alkylation of aldehydes, enabling the efficient synthesis of aliphatic ketones through ligand-controlled cross-coupling. This mild and cost-effective methodology demonstrates broad substrate compatibility with various commercially available aldehydes and both activated and unactivated alkyl bromides, delivering target products in high yields. Notably, the practical utility of this catalytic system has been highlighted through a concise two-step synthesis of the commercially valuable musk odorant Aurelione from readily available starting materials.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"39 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872742","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
Nitroalkanes as Ketone Synthetic Equivalents in C–N and C–S Bond Formation Reactions 硝基烷烃在C-N和C-S键形成反应中的酮合成等价物
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-24 DOI: 10.1021/acs.orglett.5c00948
Shubham Tiwari, Guddeangadi N. Gururaja
{"title":"Nitroalkanes as Ketone Synthetic Equivalents in C–N and C–S Bond Formation Reactions","authors":"Shubham Tiwari, Guddeangadi N. Gururaja","doi":"10.1021/acs.orglett.5c00948","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00948","url":null,"abstract":"The umpolung strategy has been explored with 2-nitropropane derivatives featuring stabilized carbanion to latent ketone equivalents. The consequence of changing intrinsic polarity at the α-carbon of nitroalkanes induces simultaneous installation of the C–N bond at the geminal and C–S bond at the vicinal positions of the nitro functionality. Although the vicinal position of nitroalkanes bears poor electronic bias, the latent ketone formation facilitates C–S bond formation in the dithiole-3-thione core structure. The application of this methodology is also demonstrated with the synthesis of amino derivatives of isothiazole-3-thione.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"15 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872925","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
Catalytic Asymmetric Hydrophosphination of α,β-Unsaturated Aza-heteroarenes α，β-不饱和氮杂芳烃的催化不对称氢化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-23 DOI: 10.1021/acs.orglett.5c01255
Lirong Chen, Guangfu Lu, Guiyong Wang, Zhifeng Ma, Baomin Fan, Yafei Guo
{"title":"Catalytic Asymmetric Hydrophosphination of α,β-Unsaturated Aza-heteroarenes","authors":"Lirong Chen, Guangfu Lu, Guiyong Wang, Zhifeng Ma, Baomin Fan, Yafei Guo","doi":"10.1021/acs.orglett.5c01255","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01255","url":null,"abstract":"Here we report a comprehensive investigation of the asymmetric addition of diarylphosphorus oxides to a wide range of α,β-unsaturated pyridines and other N-heterocyclic substrates, catalyzed by commercial chiral phosphoric acid, affording the corresponding products in up to 99% yield and 96% ee. The experimental studies and density functional theory calculation suggest the possible mechanism and the role of chiral phosphoric acid in the control of enantioselectivity.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"32 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143862643","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 Hydroalkylation of Terminal Olefins Via Decatungstate/Thiol Cooperative Photocatalysis 十钨酸盐/硫醇协同光催化催化末端烯烃轻度氢烷基化
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-04-23 DOI: 10.1021/acs.orglett.5c0108810.1021/acs.orglett.5c01088
Austin J. Moser, Paige E. Sutter, Alex M. Chavez, Sebastian A. Cruz and Julian G. West*, 
{"title":"Mild Hydroalkylation of Terminal Olefins Via Decatungstate/Thiol Cooperative Photocatalysis","authors":"Austin J. Moser,&nbsp;Paige E. Sutter,&nbsp;Alex M. Chavez,&nbsp;Sebastian A. Cruz and Julian G. West*,&nbsp;","doi":"10.1021/acs.orglett.5c0108810.1021/acs.orglett.5c01088","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01088https://doi.org/10.1021/acs.orglett.5c01088","url":null,"abstract":"<p >Here we report the use of a tetrabutylammonium decatungstate (TBADT)/thiol photocatalytic system for selective addition of acetone and other simple ketone, nitrile, and chlorocarbon functionalities to terminal olefins. This system avoids the use of energetic reagents such as peroxides and proceeds under mild conditions using Earth-abundant element catalysts, providing a sustainable approach to C–C bond formation using activated olefins. Initial exploration reveals that hydroalkylation of unactivated olefins is also possible, though in lower efficiency, and preliminary mechanistic experiments are consistent with a radical mechanism.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 17","pages":"4529–4533 4529–4533"},"PeriodicalIF":4.9,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894276","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
Catalytic Asymmetric Hydrophosphination of α,β-Unsaturated Aza-heteroarenes α，β-不饱和氮杂芳烃的催化不对称氢化反应
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-04-23 DOI: 10.1021/acs.orglett.5c0125510.1021/acs.orglett.5c01255
Lirong Chen, Guangfu Lu, Guiyong Wang, Zhifeng Ma*, Baomin Fan* and Yafei Guo*, 
{"title":"Catalytic Asymmetric Hydrophosphination of α,β-Unsaturated Aza-heteroarenes","authors":"Lirong Chen,&nbsp;Guangfu Lu,&nbsp;Guiyong Wang,&nbsp;Zhifeng Ma*,&nbsp;Baomin Fan* and Yafei Guo*,&nbsp;","doi":"10.1021/acs.orglett.5c0125510.1021/acs.orglett.5c01255","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01255https://doi.org/10.1021/acs.orglett.5c01255","url":null,"abstract":"<p >Here we report a comprehensive investigation of the asymmetric addition of diarylphosphorus oxides to a wide range of α,β-unsaturated pyridines and other N-heterocyclic substrates, catalyzed by commercial chiral phosphoric acid, affording the corresponding products in up to 99% yield and 96% ee. The experimental studies and density functional theory calculation suggest the possible mechanism and the role of chiral phosphoric acid in the control of enantioselectivity.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 17","pages":"4597–4602 4597–4602"},"PeriodicalIF":4.9,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894274","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 Hydroalkylation of Terminal Olefins Via Decatungstate/Thiol Cooperative Photocatalysis 十钨酸盐/硫醇协同光催化催化末端烯烃轻度氢烷基化
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-23 DOI: 10.1021/acs.orglett.5c01088
Austin J. Moser, Paige E. Sutter, Alex M. Chavez, Sebastian A. Cruz, Julian G. West
{"title":"Mild Hydroalkylation of Terminal Olefins Via Decatungstate/Thiol Cooperative Photocatalysis","authors":"Austin J. Moser, Paige E. Sutter, Alex M. Chavez, Sebastian A. Cruz, Julian G. West","doi":"10.1021/acs.orglett.5c01088","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01088","url":null,"abstract":"Here we report the use of a tetrabutylammonium decatungstate (TBADT)/thiol photocatalytic system for selective addition of acetone and other simple ketone, nitrile, and chlorocarbon functionalities to terminal olefins. This system avoids the use of energetic reagents such as peroxides and proceeds under mild conditions using Earth-abundant element catalysts, providing a sustainable approach to C–C bond formation using activated olefins. Initial exploration reveals that hydroalkylation of unactivated olefins is also possible, though in lower efficiency, and preliminary mechanistic experiments are consistent with a radical mechanism.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"72 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143867134","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
Synthesis of Rare 1,2,3-Triazolium-5-olates by Electrooxidative Cyclization of α-Aminocarbonyl Hydrazones α-氨基羰基腙电氧化环化合成稀有的1,2,3-三唑-5-酸酯
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-22 DOI: 10.1021/acs.orglett.5c00784
Kseniia Titenkova, Egor A. Turpakov, Daniil A. Chaplygin, Leonid L. Fershtat
{"title":"Synthesis of Rare 1,2,3-Triazolium-5-olates by Electrooxidative Cyclization of α-Aminocarbonyl Hydrazones","authors":"Kseniia Titenkova, Egor A. Turpakov, Daniil A. Chaplygin, Leonid L. Fershtat","doi":"10.1021/acs.orglett.5c00784","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00784","url":null,"abstract":"A new method for the synthesis of rare mesoionic heterocycles, namely, 1,2,3-triazolium-5-olates, via electrochemically induced intramolecular N–N bond formation was realized. The process involves electrooxidative cyclization of the readily available α-aminocarbonyl hydrazones, occurs under mild conditions, and enables the preparation of a diverse series of target mesoionics. Additionally, 1,2,3-triazolium-5-olates demonstrated high thermal stability (up to 275 °C) and feature prominent Stokes shifts (7600–8050 cm<sup>–1</sup>), which enables their application potential for analytical systems and materials science.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"42 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143862644","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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