发布求助
文献互助 智能选刊 最新文献

The Journal of Organic Chemistry最新文献

筛选
英文 中文
Correction to “Axially Chiral Trifluoromethylbenzimidazolylbenzoic Acid: A Chiral Derivatizing Agent for α-Chiral Primary Amines and Secondary Alcohols To Determine the Absolute Configuration” 更正 "轴向手性三氟甲基苯并咪唑基苯甲酸：一种用于α-手性伯胺和仲醇的手性衍生剂，用于确定绝对构型"
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-27 DOI: 10.1021/acs.joc.4c02356
Michal Kriegelstein, David Profous, Antonín Lyčka, Zdeněk Trávníček, Adam Přibylka, Tereza Volná, Sandra Benická, Petr Cankař
{"title":"Correction to “Axially Chiral Trifluoromethylbenzimidazolylbenzoic Acid: A Chiral Derivatizing Agent for α-Chiral Primary Amines and Secondary Alcohols To Determine the Absolute Configuration”","authors":"Michal Kriegelstein, David Profous, Antonín Lyčka, Zdeněk Trávníček, Adam Přibylka, Tereza Volná, Sandra Benická, Petr Cankař","doi":"10.1021/acs.joc.4c02356","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02356","url":null,"abstract":"The correct values for the <sup>19</sup>F NMR chemical shifts and their differences for several compounds appear in the table below. This article has not yet been cited by other publications.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142325837","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Carbonylative Cyclization of 2-Iodofluorobenzenes and 2-Aminophenols with Recyclable Palladium-Complexed Dendrimers on SBA-15: One-Pot Synthesis of Dibenzoxazepinones 2-Iodofluorobenzenes and 2-Aminophenols with Carbonylative Cyclization with Recyclable Palladium-Complexed Dendrimers on SBA-15：二苯并氧氮杂卓酮的一锅合成
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-27 DOI: 10.1021/acs.joc.4c01640
Qian Ye, Gang Xie, Wenyan Hao, Mingzhong Cai
{"title":"Carbonylative Cyclization of 2-Iodofluorobenzenes and 2-Aminophenols with Recyclable Palladium-Complexed Dendrimers on SBA-15: One-Pot Synthesis of Dibenzoxazepinones","authors":"Qian Ye, Gang Xie, Wenyan Hao, Mingzhong Cai","doi":"10.1021/acs.joc.4c01640","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01640","url":null,"abstract":"A novel, efficient, and practical route to dibenzoxazepinones has been developed through a one-pot heterogeneous palladium-catalyzed aminocarbonylation/aromatic nucleophilic substitution (S<sub>N</sub>Ar) sequence starting from readily available 2-iodofluorobenzenes and 2-aminophenols. The carbonylative cyclization reaction proceeds smoothly in dimethyl sulfoxide (DMSO) at 120 °C with 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) as the base by using a polyamidoamine (PAMAM)-dendronized SBA-15-supported bidentate phosphine–palladium complex [G(1)-2P-Pd(OAc)<sub>2</sub>-SBA-15] as the catalyst under 10 bar of CO, yielding a wide variety of dibenzo[<i>b,e</i>][1,4]oxazepin-11(5<i>H</i>)-one derivatives in good to excellent yields. Moreover, this new heterogenized dendritic palladium catalyst has competitive advantages in that it can be facilely recovered by simple filtration in air and recycled more than eight times without any significant loss of activity. The broad substrate scope, high functional group tolerance, and excellent palladium catalyst recyclability of the reaction make this approach a general, efficient, and economical method for the construction of valuable dibenzoxazepinone derivatives.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142325833","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Approach for Highly Enantioselective Synthesis of meta-Disubstituted [n]Paracyclophanes 元-二取代[n]对位环烷的高对映选择性合成方法
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-27 DOI: 10.1021/acs.joc.4c02021
Jia Li, Ziyang Dong, Hongxuan Zhai, Jicheng Wu, Changgui Zhao
{"title":"An Approach for Highly Enantioselective Synthesis of meta-Disubstituted [n]Paracyclophanes","authors":"Jia Li, Ziyang Dong, Hongxuan Zhai, Jicheng Wu, Changgui Zhao","doi":"10.1021/acs.joc.4c02021","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02021","url":null,"abstract":"Atroposelective synthesis of <i>meta</i>-disubstituted [<i>n</i>]paracyclophanes is a difficult task in organic chemistry. We describe a facile approach for the synthesis of <i>meta</i>-disubstituted [<i>n</i>]paracyclophanes using Pd-catalyzed enantioselective C–H olefination and sequential reductive cleavage. A wide range of [<i>n</i>]paracyclophanes was obtained with excellent enantioselectivity. Thermodynamic analysis revealed that the rotational barrier of <i>meta</i>-disubstituted [<i>n</i>]paracyclophanes was lower than that of <i>para</i>-disubstituted [<i>n</i>]paracyclophanes. The synthesized planar-chiral [14]paracyclophane showed a bright fluorescence emission and impressive circularly polarized luminescence activity.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142325835","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Modular Synthesis of Azidobicyclo[2.1.1]hexanes via (3 + 2) Annulation of α-Substituted Vinyl Azides and Bicyclo[1.1.0]butanes 通过 (3 + 2) 嵌合α-取代的乙烯基叠氮化物和双环[1.1.0]丁烷，模块化合成叠氮双环[2.1.1]己烷
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-27 DOI: 10.1021/acs.joc.4c01920
Sai Hu, Yuhong Gao, Yuming Pan, Dongshun Ni, Li Deng
{"title":"Modular Synthesis of Azidobicyclo[2.1.1]hexanes via (3 + 2) Annulation of α-Substituted Vinyl Azides and Bicyclo[1.1.0]butanes","authors":"Sai Hu, Yuhong Gao, Yuming Pan, Dongshun Ni, Li Deng","doi":"10.1021/acs.joc.4c01920","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01920","url":null,"abstract":"Here, we present a mild and rapid method to access azidobicyclo[2.1.1]hexanes via formal (3 + 2) cycloaddition of α-substituted vinyl azides and bicyclo[1.1.0]butanes under Lewis acid catalysis. A wide range of α-substituted vinyl azides were tolerated under mild conditions. Notably, the resulting cycloadducts could be transformed into structurally attractive 3-azabicyclo[3.1.1]heptenes through microwave-promoted rearrangement. The utilities were highlighted by copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of tertiary alkyl azide and further transformation of the azide and ketone groups.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142325834","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Ring-Closing Disulfenylation of Alkenoic Thioester 烯酸硫酯的闭环二硫化反应
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-26 DOI: 10.1021/acs.joc.4c02180
Kanaru Sasaki, Miari Kurihara, Hiroki Shigehisa
{"title":"Ring-Closing Disulfenylation of Alkenoic Thioester","authors":"Kanaru Sasaki, Miari Kurihara, Hiroki Shigehisa","doi":"10.1021/acs.joc.4c02180","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02180","url":null,"abstract":"This study demonstrated for the first time that alkenoic thioesters can be effectively used as nucleophiles in ring-closing disulfenylation reactions. Our investigation revealed that the reaction in hexafluoroisopropanol with an electrophilic sulfur reagent significantly enhances the product yield. We gathered experimental and theoretical evidence to support the superiority of thioesters over the traditionally used benzyl sulfide. Additionally, we explored the substrate scope and identified various factors affecting the reaction selectivity and yield.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142321890","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Polar-Effect-Directed Control in Site-Selectivity of Radical Substitution Enables C–H Perfluoroalkylation of Coumarins 极性效应定向控制自由基取代的位点选择性，使香豆素的 C-H 全氟烷基化成为可能
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-26 DOI: 10.1021/acs.joc.4c01469
Shashank Singh, Ravi P. Singh
{"title":"Polar-Effect-Directed Control in Site-Selectivity of Radical Substitution Enables C–H Perfluoroalkylation of Coumarins","authors":"Shashank Singh, Ravi P. Singh","doi":"10.1021/acs.joc.4c01469","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01469","url":null,"abstract":"A novel Ru-catalyzed protocol for C-7 selective C–H trifluoromethylation of coumarins in the presence of light is presented. This reaction undergoes a radical type nucleophilic substitution instead of a radical type electrophilic substitution owing to the benzocore activation as a result of lowering the lowest unoccupied molecular orbital (LUMO).","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142325838","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Radical Reactions with Chiral Acylammonium Salts: Synthesis of Functionalized δ-Lactams through Giese-Initiated Organocascades 手性酰基铵盐的自由基反应：通过吉斯引发的有机级联合成功能化 δ-内酰胺
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-26 DOI: 10.1021/acs.joc.4c01638
Patrick J. Sutter, Ben Walker, Kristiana Kasper, Volga Kojasoy, Dean J. Tantillo, Daniel Romo
{"title":"Radical Reactions with Chiral Acylammonium Salts: Synthesis of Functionalized δ-Lactams through Giese-Initiated Organocascades","authors":"Patrick J. Sutter, Ben Walker, Kristiana Kasper, Volga Kojasoy, Dean J. Tantillo, Daniel Romo","doi":"10.1021/acs.joc.4c01638","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01638","url":null,"abstract":"Enantioselective Giese reactions employing chiral α,β-unsaturated acylammonium salts and subsequent diastereoselective trapping followed by lactamization deliver optically active δ-lactams. Alkyl iodides bearing tosylamides undergo radical initiation using triethylborane at low temperatures to provide carbon-centered radicals to initiate the described organocascade. Subsequent diastereoselective inter- or intramolecular trapping of the incipient α-radical leads to highly functionalized, enantioenriched mono- and bicyclic δ-lactams (up to 99:1 er, &gt; 19:1 dr) bearing up to three stereogenic centers. Interestingly, benzotetramisole imparts diastereoselectivity that contradicts steric considerations alone. Results from DFT calculations rationalized the observed enantio- and diastereoselectivities, revealed an electrostatic interaction between the sulfone oxygens and the ammonium cation in the initial α-radical intermediate, and aided in application of this methodology to bicyclic δ-lactams through intramolecular trapping of the α-radical intermediate.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142321881","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
CuI-Catalyzed Selenylation of Pyrrolo[2,1-a]isoquinolines and Other Electron-Rich Heteroarenes CuI 催化的吡咯并[2,1-a]异喹啉和其他富电子杂环戊烯的硒化反应
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-26 DOI: 10.1021/acs.joc.4c01462
Jing Zhou, Jia-Yi Han, Xin Yu, Liu Yang, Man Jiang, Yun-Meng Li, Hai-Lei Cui
{"title":"CuI-Catalyzed Selenylation of Pyrrolo[2,1-a]isoquinolines and Other Electron-Rich Heteroarenes","authors":"Jing Zhou, Jia-Yi Han, Xin Yu, Liu Yang, Man Jiang, Yun-Meng Li, Hai-Lei Cui","doi":"10.1021/acs.joc.4c01462","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01462","url":null,"abstract":"We have established a mild CuI-catalyzed selenylation of pyrrolo[2,1-<i>a</i>]isoquinoline derivatives in the presence of <i>m</i>CPBA (<i>m</i>-chloroperoxybenzoic acid) at ambient temperature. Corresponding organoselenides have been prepared readily in 53–92% yields. This process can also be expanded to the modification of pyrroles, azaindole, and indoles, delivering the desired heterocyclic selenides in moderate to good yields.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142321901","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Driven Synthesis of Vinyl Amines without Photocatalyst 不使用光催化剂的乙烯基胺可见光驱动合成法
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-26 DOI: 10.1021/acs.joc.4c01624
Koustav Pal, Debabrata Das, Krishna Gopal Ghosh, Devarajulu Sureshkumar
{"title":"Visible-Light Driven Synthesis of Vinyl Amines without Photocatalyst","authors":"Koustav Pal, Debabrata Das, Krishna Gopal Ghosh, Devarajulu Sureshkumar","doi":"10.1021/acs.joc.4c01624","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01624","url":null,"abstract":"We developed a visible-light-induced vinyl amination of activated alkenes using TMSN<sub>3</sub> and CsF through EDA complex formation under an oxygen atmosphere. Without light, the EDA complex forms between activated alkene, CsF, and oxygen. Upon exposure to light, oxygen in the complex gets excited, initiating the HAT process. This method efficiently synthesizes vinyl-amine derivatives via a radical pathway, demonstrating good functional group tolerance and high yields in a short time. Further, the late-stage functionalization enables the synthesis of biologically active heterocycles.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142325862","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Base-Mediated Visible-Light-Driven C–H Arylation of Quinoxalin-2(1H)-Ones in Ethanol 乙醇中碱介导的可见光驱动的喹喔啉-2(1H)-酮的 C-H 芳基化反应
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-26 DOI: 10.1021/acs.joc.4c01641
Yitong Pan, Luohe Wang, Yunhong Shi, Guoqing Huang, Xiubin Bu, Xiaobo Yang, Zhen Zhao
{"title":"Base-Mediated Visible-Light-Driven C–H Arylation of Quinoxalin-2(1H)-Ones in Ethanol","authors":"Yitong Pan, Luohe Wang, Yunhong Shi, Guoqing Huang, Xiubin Bu, Xiaobo Yang, Zhen Zhao","doi":"10.1021/acs.joc.4c01641","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01641","url":null,"abstract":"Prior methods for visible-light-driven C–H arylation of quinoxalin-2(1<i>H</i>)-ones relied on external photocatalysts. Herein, we report a photocatalyst-free approach for this arylation. In this approach, β-dicarbonyl iodonium ylides, combined with <i>t</i>-BuOK in ethanol, act as aryl precursors, forming electron donor–acceptor (EDA) complexes. These complexes enhance light absorption, facilitating efficient single electron transfer and aryl radical formation. Consequently, various quinoxalin-2(1<i>H</i>)-ones undergo precise and efficient arylation without external photocatalysts. This protocol exhibits excellent tolerance toward diverse functional groups, with mild reaction conditions and eco-friendly solvents, revealing a high Ecoscale value.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142321882","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
下一页 尾页
0
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整，为了账户安全，请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
请完成安全验证×
相关产品
×
本文献相关产品
联系我们：info@booksci.cn Book学术提供免费学术资源搜索服务，方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号：481959085
Book学术官方微信