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Synthesis of Biaryl Atropisomers via Site-Selective C-H Functionalization.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 DOI: 10.1021/acs.orglett.5c00121
Jason C Genova, David A Nicewicz
{"title":"Synthesis of Biaryl Atropisomers via Site-Selective C-H Functionalization.","authors":"Jason C Genova, David A Nicewicz","doi":"10.1021/acs.orglett.5c00121","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00121","url":null,"abstract":"<p><p>We describe an approach to form conformationally rigid atropisomers with a variety of nucleophiles not commonly applicable to transition-metal-catalyzed methods. The use of organic photoredox catalysis renders this method operationally simple, as direct substrate oxidation followed by nucleophilic attack may furnish the products via site-selective C-H functionalization in moderate to quantitative yields. Density functional theory (DFT) computations estimated the rotational barriers and half-lives of the products.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143416851","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
An Electrochemical Design for a General Catalytic Carboxylic Acid Substitution Platform via Anhydrides at Room Temperature: Amidation, Esterification, and Thioesterification.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 DOI: 10.1021/acs.orglett.5c00103
Jian Han, Jacob J Piane, Hannah Gizenski, Elizabeth Elacqua, Eric D Nacsa
{"title":"An Electrochemical Design for a General Catalytic Carboxylic Acid Substitution Platform via Anhydrides at Room Temperature: Amidation, Esterification, and Thioesterification.","authors":"Jian Han, Jacob J Piane, Hannah Gizenski, Elizabeth Elacqua, Eric D Nacsa","doi":"10.1021/acs.orglett.5c00103","DOIUrl":"10.1021/acs.orglett.5c00103","url":null,"abstract":"<p><p>An original concept for catalytic electrochemical dehydration has enabled a suite of acid substitutions, including amidation, esterification, and thioesterification, through a linchpin anhydride formed in situ. By avoiding stoichiometric dehydrating agents, this method addresses a leading challenge in organic synthesis and green chemistry. It also proceeds without acid additives at room temperature, accesses a diverse range of product structures, is easily scaled, and enabled the first example of catalytic peptide coupling at room temperature.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143412397","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
Regioselective Aryne Annulations of N-Tosyl-2-enamides and N-tert-Butylsulfinyl-2-enamides for the Construction of Dihydroquinolin-4-one and Chroman-4-imine Units
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-14 DOI: 10.1021/acs.orglett.4c04571
Aimin Zhang, Suh Young Yu, Jihye Lee, Sehui Yang, Junseong Lee, Jimin Kim
{"title":"Regioselective Aryne Annulations of N-Tosyl-2-enamides and N-tert-Butylsulfinyl-2-enamides for the Construction of Dihydroquinolin-4-one and Chroman-4-imine Units","authors":"Aimin Zhang, Suh Young Yu, Jihye Lee, Sehui Yang, Junseong Lee, Jimin Kim","doi":"10.1021/acs.orglett.4c04571","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04571","url":null,"abstract":"A regioselective synthesis of the dihydroquinolin-4-one <b>4</b> is achieved from the aryne-mediated annulation of an <i>o</i>-(trimethylsilyl)aryl triflate <b>1</b> with <i>N</i>-tosyl-2-enamide <b>2</b> in the presence of TBAT in toluene, whereas the chroman-4-imine <b>5</b> is formed from the reaction of <b>1</b> with <i>N</i>-(<i>tert</i>-butylsulfinyl)-2-enamide <b>3</b> and TBAF in THF. Governing factors for regioselectivity have been accounted for as strong steric and electronic effects between <i>N</i>-toluenesulfonyl and <i>N</i>-<i>tert</i>-butylsulfinyl groups in <b>2</b> and <b>3</b>. The methods described herein are successful with various substrates <b>1</b> with <b>2</b> or <b>3</b> in high levels of regioselectivity, and diastereoselectivity for <b>5</b>.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"80 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143418425","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
Bay-Aminated Octaazaperopyrenedioxides (OAPPDOs) as Precursors for Diazepine and Diazepinone Derivatives.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 Epub Date: 2025-01-30 DOI: 10.1021/acs.orglett.4c04686
Robert Eichelmann, Kai Bender, Julius A Guenther, Levi A Ziegenhagen, Joachim Ballmann, Lutz H Gade
{"title":"<i>Bay</i>-Aminated Octaazaperopyrenedioxides (OAPPDOs) as Precursors for Diazepine and Diazepinone Derivatives.","authors":"Robert Eichelmann, Kai Bender, Julius A Guenther, Levi A Ziegenhagen, Joachim Ballmann, Lutz H Gade","doi":"10.1021/acs.orglett.4c04686","DOIUrl":"10.1021/acs.orglett.4c04686","url":null,"abstract":"<p><p>Fully <i>bay</i>-aminated octaazaperopyrenedioxide (OAPPDO) derivatives have been accessible via Buchwald-Hartwig amination of the <i>bay</i>-chlorinated starting material. They were isolated as semiquinoidal species with a bent polycyclic core and characterized as nonfluorescent charge-transfer dyes. The corresponding secondary amines were synthesized by reduction and displayed typical absorption and emission behavior for perylene derivatives. One of the reduced amines served as a precursor for conversion of the secondary amino groups to 1,3-diazepine and -diazepinone units spanning the <i>bay</i>-area - seven-membered ring motifs hitherto unknown in perylene chemistry. The photophysical and electrochemical properties of the azaperylene dyes were investigated by absorption and emission spectroscopy supported by time-dependent density functional theory methods and cyclic voltammetry as well as differential pulse voltammetry.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"1396-1401"},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143062246","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
N2-Alkylation of 1,2,3-Triazoles with Ethers under Thermodynamical Control.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 Epub Date: 2025-01-31 DOI: 10.1021/acs.orglett.4c04754
Hui Zhang, Zijian Zhang, Lifang Tian, Yanfeng Han, Peijun Zhao, Honglei Yang, Jiawei Li, Guanglu Liu, Li-Li Zhu, Yahui Wang
{"title":"N<sup>2</sup>-Alkylation of 1,2,3-Triazoles with Ethers under Thermodynamical Control.","authors":"Hui Zhang, Zijian Zhang, Lifang Tian, Yanfeng Han, Peijun Zhao, Honglei Yang, Jiawei Li, Guanglu Liu, Li-Li Zhu, Yahui Wang","doi":"10.1021/acs.orglett.4c04754","DOIUrl":"10.1021/acs.orglett.4c04754","url":null,"abstract":"<p><p>Herein, a relay strategy incorporating oxidative cross dehydrogenative coupling (CDC) and N<sup>1</sup>- to N<sup>2</sup>-isomerization is disclosed for the formal N<sup>2</sup>-selective alkylation of triazoles with ethers under thermodynamic control conditions. By taking advantage of the different thermodynamical stabilities of N<sup>1</sup>- and N<sup>2</sup>-alkylated triazoles (3.65 kcal/mol), the initially formed N<sup>1</sup>-isomers can be <i>in situ</i> converted into their more stable N<sup>2</sup>-isomers when reaching thermodynamic equilibrium. PhI(OAc)<sub>2</sub> has been discovered to function as both an oxidant for the CDC process and an efficient mediator for the isomerization step.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"1428-1433"},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143062407","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
Photocatalytic Tandem Ueno-Stork Cyclization/Intermolecular Giese Addition Sequence for Stereoselective Difunctionalization of Allylic Alcohols.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 DOI: 10.1021/acs.orglett.5c00287
Yuki Tateishi, Shota Nagasawa, Yoshiharu Iwabuchi
{"title":"Photocatalytic Tandem Ueno-Stork Cyclization/Intermolecular Giese Addition Sequence for Stereoselective Difunctionalization of Allylic Alcohols.","authors":"Yuki Tateishi, Shota Nagasawa, Yoshiharu Iwabuchi","doi":"10.1021/acs.orglett.5c00287","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00287","url":null,"abstract":"<p><p>Herein, we report a novel photocatalytic tandem Ueno-Stork cyclization/intermolecular Giese addition sequence for the stereoselective difunctionalization of allylic alcohols. This reaction avoids the use of toxic reagents and complicated protocols typically required under classical Ueno-Stork conditions. Furthermore, the reaction system demonstrated good stereoselectivity with both cyclic and linear allylic alcohols.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143416844","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
Assembly of Biaryl Amines via Mild Copper-Catalyzed Coupling of Anilines with (Hetero)aryl Chlorides/Bromides.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 Epub Date: 2025-01-31 DOI: 10.1021/acs.orglett.5c00004
Sailuo Li, Lanting Xu, Bang An, Dawei Ma
{"title":"Assembly of Biaryl Amines via Mild Copper-Catalyzed Coupling of Anilines with (Hetero)aryl Chlorides/Bromides.","authors":"Sailuo Li, Lanting Xu, Bang An, Dawei Ma","doi":"10.1021/acs.orglett.5c00004","DOIUrl":"10.1021/acs.orglett.5c00004","url":null,"abstract":"<p><p>CuI/6-hydroxy picolinohydrazide-catalyzed coupling of (hetero)aryl chlorides with anilines proceeded well at 100 °C to afford biaryl amines in a diverse manner, which represents the first example of Cu-catalyzed biaryl amines under milder conditions. The same catalytic system could make the coupling of (hetero)aryl bromides with anilines work at room temperature, giving the corresponding products with an excellent reaction scope.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"1498-1503"},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143062255","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
Enantioselective Cobalt-Catalyzed Remote Hydroboration of Alkenylboronates.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 DOI: 10.1021/acs.orglett.5c00107
Wenke Dong, Zheming Liu, Anbang Bai, Xiaoyu Zhang, Peiwen Han, Jingyi He, Chenchen Li
{"title":"Enantioselective Cobalt-Catalyzed Remote Hydroboration of Alkenylboronates.","authors":"Wenke Dong, Zheming Liu, Anbang Bai, Xiaoyu Zhang, Peiwen Han, Jingyi He, Chenchen Li","doi":"10.1021/acs.orglett.5c00107","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00107","url":null,"abstract":"<p><p>Heteroatomic groups in alkenes typically direct thermodynamically favored chain walking of C═C bonds toward themselves, thereby facilitating C-H bond functionalization near the heteroatoms. We present herein an efficient cobalt-catalyzed contra-thermodynamic remote hydroboration of alkenylboronates with pinacolborane to synthesize chiral 1,<i>n</i>-diboronates. This protocol features a broad substrate scope, high functional group tolerance, and excellent enantioselectivity. Mechanistic studies indicate the involvement of a chain-walking process. Gram-scale reactions and various product derivatizations further highlight its practicality.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143412399","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
Intramolecular Friedel-Crafts Reactions of Sulfamoyl Fluorides, Fluorosulfates, and Sulfuramidimidoyl Fluorides.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 Epub Date: 2025-01-30 DOI: 10.1021/acs.orglett.4c04464
Taijie Guo, Long Xu, Jiajia Dong
{"title":"Intramolecular Friedel-Crafts Reactions of Sulfamoyl Fluorides, Fluorosulfates, and Sulfuramidimidoyl Fluorides.","authors":"Taijie Guo, Long Xu, Jiajia Dong","doi":"10.1021/acs.orglett.4c04464","DOIUrl":"10.1021/acs.orglett.4c04464","url":null,"abstract":"<p><p>Sultams are valuable heterocycles with numerous applications, particularly as pharmacophores. Previous syntheses of these compounds usually require metal-catalyzed cyclization or multiple-step processes. Here, we report a straightforward strategy for accessing these important motifs by developing the intramolecular Friedel-Crafts cyclization of sulfamoyl fluorides under mild conditions. Our protocol also accommodates fluorosulfates and sulfuramidimidoyl fluorides, which are rarely utilized in Friedel-Crafts reactions.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"1356-1361"},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143062317","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
Enantio- and Regioselective Propargylation and Allenylation of β,γ-Unsaturated α-Ketoesters with Allenyl Boronate Regulated by Chiral Copper/Zinc.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 Epub Date: 2025-01-31 DOI: 10.1021/acs.orglett.4c03845
Shuai-Ru Cheng, Ni Zhao, Wei Ma, Guo-Rong Ma, Pei Wang
{"title":"Enantio- and Regioselective Propargylation and Allenylation of β,γ-Unsaturated α-Ketoesters with Allenyl Boronate Regulated by Chiral Copper/Zinc.","authors":"Shuai-Ru Cheng, Ni Zhao, Wei Ma, Guo-Rong Ma, Pei Wang","doi":"10.1021/acs.orglett.4c03845","DOIUrl":"10.1021/acs.orglett.4c03845","url":null,"abstract":"<p><p>A method for asymmetric propargylation and allenylation of β,γ-unsaturated α-ketoesters catalyzed by Box-Cu/Box-Zn using a commercial organoboron reagent is reported. The reaction was demonstrated to be broadly tolerant of functional groups, resulting in a series of propargyl and allenyl tertiary alcohols in excellent yields with high enantio- and regioselectivities. Furthermore, the proposed mechanism was supported by density functional theory calculations. Gram-scale experiments as well as the synthesis of various chiral tertiary alcohols and glycol derivatives demonstrated the practicality of this synthetic strategy.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"1327-1334"},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143070784","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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