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Cobalt-Catalyzed Regioselective Intramolecular Hydrosilylation of Olefins to Access Sila-heterocycles 钴催化烯烃分子内区域选择性硅氢化反应制备硅杂环
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-25 DOI: 10.1021/acs.orglett.5c01071
Teng-Teng Wu, Zi-Lu Wang, Yun-He Xu
{"title":"Cobalt-Catalyzed Regioselective Intramolecular Hydrosilylation of Olefins to Access Sila-heterocycles","authors":"Teng-Teng Wu, Zi-Lu Wang, Yun-He Xu","doi":"10.1021/acs.orglett.5c01071","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01071","url":null,"abstract":"An efficient and straightforward cobalt-catalyzed regioselective intramolecular hydrosilylation of olefins has been developed. Regioselectivity is controlled by the choice of ligands and substrates, which operate through two distinct mechanisms. This method has been successfully applied to both terminal and internal alkenes and phenyl and alkyl tethers between the silane and the alkene, demonstrating its versatility across a broad range of substrates.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"140 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872923","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
Room Temperature Access to Bridged Nitrogen Ligands via Electroreductive Annulation of 1,10-Phenanthrolines and Imines 通过1,10-菲罗啉和亚胺的电还原环化在室温下获得桥接氮配体
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-25 DOI: 10.1021/acs.orglett.5c01140
Chengqian Zhang, Maorui Wang, Min Zhang
{"title":"Room Temperature Access to Bridged Nitrogen Ligands via Electroreductive Annulation of 1,10-Phenanthrolines and Imines","authors":"Chengqian Zhang, Maorui Wang, Min Zhang","doi":"10.1021/acs.orglett.5c01140","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01140","url":null,"abstract":"An electroreductive annulation reaction of 1,10-phenanthrolines and imines has been developed. This method proceeds with broad substrate and functionality tolerance, high selectivity, and no need for pressurized H<sub>2</sub> gas or transition metal catalysts. Mechanistic studies reveal that the products are formed via simultaneous electroreduction of both proton-activated reactants followed by radical cross-coupling and intramolecular cyclization of the coupling adduct.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"3 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872924","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
BBr3-Mediated ortho C–H Borylation of Benzamides bbr3介导的苯酰胺邻位C-H硼化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-25 DOI: 10.1021/acs.orglett.5c00822
Yixuan Liang, Chengyu Du, Chengwen Dong, Jinxi Cao, Yijia Xu, Hua Zhang
{"title":"BBr3-Mediated ortho C–H Borylation of Benzamides","authors":"Yixuan Liang, Chengyu Du, Chengwen Dong, Jinxi Cao, Yijia Xu, Hua Zhang","doi":"10.1021/acs.orglett.5c00822","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00822","url":null,"abstract":"We have developed a BBr<sub>3</sub>-mediated, metal-free <i>ortho</i> C–H borylation of benzamides, enabling the synthesis of a wide range of <i>ortho</i>-borylated benzamides in moderate to good yields. This transformation offers a convenient strategy for accessing functionalized benzamides, which are valuable intermediates in pharmaceuticals, agrochemicals, and fine chemical synthesis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"7 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143876180","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
TEMPO-Mediated Electrochemical α-Allylation of Tetrahydroisoquinolines tempo介导的四氢异喹啉类化合物α-烯丙基化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-25 DOI: 10.1021/acs.orglett.5c00738
Youliang He, Zhen-Hua Wang, Hui-Lin Liu, Ping Fang, Cong Ma, Hao Xu, Tian-Sheng Mei
{"title":"TEMPO-Mediated Electrochemical α-Allylation of Tetrahydroisoquinolines","authors":"Youliang He, Zhen-Hua Wang, Hui-Lin Liu, Ping Fang, Cong Ma, Hao Xu, Tian-Sheng Mei","doi":"10.1021/acs.orglett.5c00738","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00738","url":null,"abstract":"A C(sp<sup>3</sup>)–H allylation of tetrahydroisoquinolines has been developed by combining Shono oxidation with a vinylogous Mannich-type reaction. TEMPO was used as the electrocatalyst to lower the electrode potential, improving functional group compatibility. This method provided a practical and efficient tandem procedure for the α-allylation of tetrahydroisoquinolines. The reaction proceeded through the formation of an iminium cation intermediate, which was generated in situ by anodic oxidation, followed by nucleophilic addition of 2-allylazaarenes.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872921","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 Oxidative Reassembly of 1,3-Diketones with Aryl Alkenes and Water via Carbon–Carbon Bond Cleavage Rearrangement 1,3-二酮与芳基烯烃和水的碳-碳键裂解重排电化学氧化重组
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-25 DOI: 10.1021/acs.orglett.5c00929
Wei Wu, Rongxing Linghu, Bingjie Jian, Jun Shi, Qin Chi, Biaobiao Jiang, Hai Ren
{"title":"Electrochemical Oxidative Reassembly of 1,3-Diketones with Aryl Alkenes and Water via Carbon–Carbon Bond Cleavage Rearrangement","authors":"Wei Wu, Rongxing Linghu, Bingjie Jian, Jun Shi, Qin Chi, Biaobiao Jiang, Hai Ren","doi":"10.1021/acs.orglett.5c00929","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00929","url":null,"abstract":"We report the electrochemical cleavage and reassembly of 1,3-diketones with aryl alkenes and water for the synthesis of 1,4-ketoalcohol derivatives. This approach represents the first example of formal carbon–carbon cleavage of 1,3-diketones and alkene insertion via electro-oxidation, enabling the direct synthesis of diverse 1,4-ketoalcohol derivatives in good to high yields. The developed strategy employs an electrochemical approach using inexpensive commercial carbon electrodes in an undivided cell under mild and operationally simple conditions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"2 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872922","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 5.2 1区 化学
Organic Letters Pub Date : 2025-04-24 DOI: 10.1021/acs.orglett.5c00811
Xiang Liu, Hexiang Wang, Dongrong Lin, Zhen Lin, Qiye Chen, Baofu Zhu, 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, Hexiang Wang, Dongrong Lin, Zhen Lin, Qiye Chen, Baofu Zhu, Hua Cao","doi":"10.1021/acs.orglett.5c00811","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00811","url":null,"abstract":"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.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"14 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143867125","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
Divergent Synthesis of Dihydrofuran and Dienol Scaffolds via Pd-Catalyzed Decarboxylative Carbene Cross-Coupling pd催化脱羧羰基交叉偶联合成二氢呋喃和二烯醇支架
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-24 DOI: 10.1021/acs.orglett.5c01198
Xiaolong Ma, Erfei Miao, Yili Sun, Longkang Sun, Chaoying Huang, Xun Zhang, Ke-Qiang Hou, Zhongliang Xu, Yi Zang, Tongyu Bi, Weibo Yang
{"title":"Divergent Synthesis of Dihydrofuran and Dienol Scaffolds via Pd-Catalyzed Decarboxylative Carbene Cross-Coupling","authors":"Xiaolong Ma, Erfei Miao, Yili Sun, Longkang Sun, Chaoying Huang, Xun Zhang, Ke-Qiang Hou, Zhongliang Xu, Yi Zang, Tongyu Bi, Weibo Yang","doi":"10.1021/acs.orglett.5c01198","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01198","url":null,"abstract":"Herein, we report a novel ligand-switchable Pd-catalyzed carbene coupling reaction employing vinylethylene carbonates and sulfoxonium ylides. By proper choice of ligands, the chemoselectivity of the process could be efficiently regulated, allowing for the availability of dihydrofuran or dienol scaffolds. This method features mild reaction conditions, broad scope, and remarkable synthetic utility. Compound <b>6f</b> can effectively stimulate the secretion of GLP-1, providing promising insight into the development of small-molecule agonists for the GLP-1 receptor.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"25 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143867126","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
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 4.9 1区 化学
Organic Letters Pub Date : 2025-04-24 DOI: 10.1021/acs.orglett.5c0112710.1021/acs.orglett.5c01127
Soo Young Kim, Juho Lee, Won Seok Ham, Tae Yeong Im, Su Yong Go and Hong Geun Lee*, 
{"title":"Dual Activation of Organoboron for the Ion-Pair-Mediated Synthesis of Hindered Alkyl Fluorides","authors":"Soo Young Kim,&nbsp;Juho Lee,&nbsp;Won Seok Ham,&nbsp;Tae Yeong Im,&nbsp;Su Yong Go and Hong Geun Lee*,&nbsp;","doi":"10.1021/acs.orglett.5c0112710.1021/acs.orglett.5c01127","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01127https://doi.org/10.1021/acs.orglett.5c01127","url":null,"abstract":"<p >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.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 17","pages":"4559–4564 4559–4564"},"PeriodicalIF":4.9,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894114","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
Functionalized Oxindole Construction via a Cyano Migration and Cyclization Relay Strategy 基于氰基迁移和环化中继策略的功能化氧吲哚构建
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-24 DOI: 10.1021/acs.orglett.5c00899
Bo-Xi Liu, Syed Anis Ali Shah, Feng Zhou, Weidong Rao, Shu-Su Shen, Daopeng Sheng, Shun-Yi Wang
{"title":"Functionalized Oxindole Construction via a Cyano Migration and Cyclization Relay Strategy","authors":"Bo-Xi Liu, Syed Anis Ali Shah, Feng Zhou, Weidong Rao, Shu-Su Shen, Daopeng Sheng, Shun-Yi Wang","doi":"10.1021/acs.orglett.5c00899","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00899","url":null,"abstract":"A visible-light-induced trifunctionalization of unactivated alkenes for building functionalized oxindoles through a radical cyano migration strategy is reported. This transformation employs a tandem alkene sulfonylation-initiated cyano migration/cyclization cascade process. This strategy features stable and easily accessible substrates, mild reaction conditions, metal-free catalysts, and the capability of late-stage functionalization.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"140 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872847","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 Modular and Scalable Route to Protected Cyclopropane Amino Acid Building Blocks 保护环丙烷氨基酸构建块的模块化和可扩展路线
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-24 DOI: 10.1021/acs.orglett.5c01341
Charlie T. Swan, Alex G. Edmonds, Stephen P. Argent, Nicholas J. Mitchell
{"title":"A Modular and Scalable Route to Protected Cyclopropane Amino Acid Building Blocks","authors":"Charlie T. Swan, Alex G. Edmonds, Stephen P. Argent, Nicholas J. Mitchell","doi":"10.1021/acs.orglett.5c01341","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01341","url":null,"abstract":"An improved method for the synthesis of noncanonical cyclopropane amino acids from common laboratory reagents is described, avoiding the use of neurotoxic oxidants or precious metal catalysts. Intramolecular isocyanate trapping via a Hofmann rearrangement permits the synthesis of bicyclic carbamates in an enantioenriched and diastereopure manner. Subsequent ring-opening of these species allows access to cyclopropane amino acids which can be further functionalized via oxidation and S<sub>N</sub>2 pathways and incorporated into peptides via solid-phase peptide synthesis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"7 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143867132","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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