发布求助
文献互助 智能选刊 最新文献

Journal of Organic Chemistry最新文献

筛选
英文 中文
Synthesis and Elaboration of Medium-Sized Ring Building Blocks Prepared via Cascade Ring Expansion Reactions 通过级联扩环反应制备的中型环状结构单元的合成与阐释
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1021/acs.joc.5c00202
Haimei Zhou, Peter O’Brien, William P. Unsworth
{"title":"Synthesis and Elaboration of Medium-Sized Ring Building Blocks Prepared via Cascade Ring Expansion Reactions","authors":"Haimei Zhou, Peter O’Brien, William P. Unsworth","doi":"10.1021/acs.joc.5c00202","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00202","url":null,"abstract":"A general approach is described for the synthesis and elaboration of medium-sized ring mono- and difunctionalized 8- or 9-membered ring lactone building blocks. The lactones are prepared via cascade ring expansion reactions and elaborated via Suzuki–Miyaura cross coupling and various <i>N</i>-functionalization reactions. This enables efficient access to diverse, medium-sized ring building blocks in a synthetically challenging and under-represented area of the pharmaceutical chemical space.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"38 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143758478","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
Mechanistic Insights into the Propagation Cycle of the Hofmann–Löffler–Freytag Reaction: Halogen vs Hydrogen Atom Transfer
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1021/acs.joc.4c02997
Gabrijel Zubčić, Luka Andrijanić, Iva Džeba, Jiangyang You, Tomislav Friganović, Tomislav Portada, Kristina Pavić, Erim Bešić, Valerije Vrček, Davor Šakić
{"title":"Mechanistic Insights into the Propagation Cycle of the Hofmann–Löffler–Freytag Reaction: Halogen vs Hydrogen Atom Transfer","authors":"Gabrijel Zubčić, Luka Andrijanić, Iva Džeba, Jiangyang You, Tomislav Friganović, Tomislav Portada, Kristina Pavić, Erim Bešić, Valerije Vrček, Davor Šakić","doi":"10.1021/acs.joc.4c02997","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02997","url":null,"abstract":"The Hofmann–Löffler–Freytag (HLF) reaction is a method that employs N-chlorinated precursors in radical-mediated rearrangement cycles to synthesize pyrrolidine rings and C–H functionalized products. This study aims to elucidate the mechanism of the propagation cycle, identify the rate-limiting step, and uncover the factors influencing the regioselectivity of the HLF reaction. Combining experimental techniques─laser flash photolysis (LFP), electron paramagnetic resonance (EPR), and nuclear magnetic resonance (NMR)─with computational density functional theory (DFT) calculations and kinetic modeling, we challenge the previous assumption that the hydrogen atom transfer (HAT) step was rate-limiting and regioselectivity was under both thermodynamic and kinetic control. We have identified that the halogen atom transfer (XAT) step in the propagation cycle of the HLF reaction follows pseudo-first-order kinetics and has the largest transition-state barrier. Additionally, we observed that regioselectivity is exclusively controlled by the intramolecular hydrogen atom transfer kinetics, while no thermodynamic preference exists in the formation of C<sub>6</sub>- and C<sub>5</sub>-chlorinated products. Our work predicts how to accelerate the HLF reaction and how we can control the regioselectivity by the smarter selection of substrates based on calculations, which could provide better control of the reaction when implemented in organic synthesis.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"58 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745240","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
Synthesizing Chiral Vicinal Bisphosphine Derivatives through Hydrophosphinylation and Asymmetric Protonation of Secondary Phosphine Sulfides with Vinylphosphine Oxides 通过仲膦硫化物与乙烯基氧化膦的氢化膦酰化和不对称质子化合成手性手性双膦衍生物
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1021/acs.joc.5c00414
Eiki Hirota, Shin-ichi Hirashima, Chika Tadasue, Anna Suzuki, Yasuyuki Matsushima, Kosuke Nakashima, Tsuyoshi Miura
{"title":"Synthesizing Chiral Vicinal Bisphosphine Derivatives through Hydrophosphinylation and Asymmetric Protonation of Secondary Phosphine Sulfides with Vinylphosphine Oxides","authors":"Eiki Hirota, Shin-ichi Hirashima, Chika Tadasue, Anna Suzuki, Yasuyuki Matsushima, Kosuke Nakashima, Tsuyoshi Miura","doi":"10.1021/acs.joc.5c00414","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00414","url":null,"abstract":"Herein, we report bifunctional iminophosphorane-catalyzed hydrophosphinylation and asymmetric protonation of secondary phosphine sulfides with vinylphosphine oxides. This reaction efficiently afforded chiral vicinal bisphosphine derivatives in high yields with excellent enantioselectivities (up to 99% yield and 95% ee). Furthermore, the produced chiral vicinal bisphosphine derivatives could be readily transformed into vicinal bisphosphines and vicinal bisphosphine monosulfides. This study presents the first methodology for using secondary phosphine sulfides as pronucleophiles in asymmetric protonation reactions.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"38 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143758487","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
Au(I) /Brønsted Acid Relay-Catalyzed Benzannulation Reaction of Alkynylbenzaldehydes and Styrenes for the Synthesis of Substituted Naphthalenes
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1021/acs.joc.4c03186
Yuanzhen Xu, Shaolong Zheng, Yun Li
{"title":"Au(I) /Brønsted Acid Relay-Catalyzed Benzannulation Reaction of Alkynylbenzaldehydes and Styrenes for the Synthesis of Substituted Naphthalenes","authors":"Yuanzhen Xu, Shaolong Zheng, Yun Li","doi":"10.1021/acs.joc.4c03186","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03186","url":null,"abstract":"We report herein an Au(I) /Brønsted acid relay-catalyzed tandem benzannulation reaction of alkynylbenzaldehydes and styrenes for the synthesis of substituted naphthalenes. This reaction sequence involves Au(I)-catalyzed alkyne cycloisomerization, oxa-[4 + 2]-cycloaddition, α-ketol rearrangement, and aromatization to access substituted naphthalenes in moderate-to-good yields. The resulting substituted naphthalenes are further subjected to Brønsted acid catalysis, promoting Friedel–Crafts reactions to form chrysene derivatives in excellent yields.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"15 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745264","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
From Cortisone to Enlicitide: A Journey of Synthetic Chemistry Innovations at Merck
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1021/acs.joc.4c02919
Louis-Charles Campeau
{"title":"From Cortisone to Enlicitide: A Journey of Synthetic Chemistry Innovations at Merck","authors":"Louis-Charles Campeau","doi":"10.1021/acs.joc.4c02919","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02919","url":null,"abstract":"Necessity is the mother of invention. Most synthetic chemistry innovations are driven by our desire to make molecules. In the first half of the 20th century, much of this work was inspired by natural products, but as we started to understand the impact that specific molecules could have on biology and human health, a new stimulus for invention appeared. The pharmaceutical industry first brought mass production and formulation of natural products for medicinal purposes but quickly started tinkering with molecular structure to modify compounds’ properties, eventually designing molecules from scratch. This necessity for invention of new molecules to improve human health and to manufacture them on large scale is an excellent stimulus for synthetic chemistry innovations. In this Perspective, examples from Merck’s chemistry groups are used to highlight the types of innovations that can arise from these endeavors.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"73 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143758476","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
Reactions of Cyclopropenones with 2-Picolines: The Multistep Aerobic Cascade toward [2.3.3]Cyclazinylium-1-olates
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1021/acs.joc.4c02643
Ilya V. Nechaev, Georgij V. Cherkaev
{"title":"Reactions of Cyclopropenones with 2-Picolines: The Multistep Aerobic Cascade toward [2.3.3]Cyclazinylium-1-olates","authors":"Ilya V. Nechaev, Georgij V. Cherkaev","doi":"10.1021/acs.joc.4c02643","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02643","url":null,"abstract":"Aerobic nonlinear cascade reaction between 2-substituted cyclopropenones and 2-picolines was discovered to afford rare pyrrolo[2,1,5-<i>de</i>]quinolizin-9-ium-1-olates ([2.3.3]cyclazinylium-1-olates). The reaction mechanism was studied by labeling experiments, LC-MS/NMR monitoring, and intermediates trapping. The reaction features and limitations were highlighted, and focusing on the side processes allowed the demonstration of examples of gaining high molecular complexity from simple reactants. Optical properties of the [2.3.3]cyclazinylium-1-olates and their aza-analogs were explored, and some structure–property relationships and mesomerism particularities were revealed.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745263","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
Regioselective α-Allylation of Cyclic Allylborates with Allylic Bromides
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-31 DOI: 10.1021/acs.joc.5c00135
Go Yamagiwa, Hiroki Murata, Kazuhiko Semba, Tetsuaki Fujihara
{"title":"Regioselective α-Allylation of Cyclic Allylborates with Allylic Bromides","authors":"Go Yamagiwa, Hiroki Murata, Kazuhiko Semba, Tetsuaki Fujihara","doi":"10.1021/acs.joc.5c00135","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00135","url":null,"abstract":"Allylic boron compounds are valuable nucleophiles for introducing allylic moieties into organic compounds. While numerous examples of γ-selective functionalization, such as the allylboration of carbonyl compounds, have been reported, α-selective carbon–carbon bond formation involving allylborates remains limited. In this study, α-selective allylation of cyclic allylborates was achieved using allylic bromides as carbon-based electrophiles. The reaction between cyclic allylborates and allylic bromides produced various allylboronates in moderate to good yields.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745266","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
Mechanochemical Functionalization of Heterocycles by C–H Activation: An Update
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-31 DOI: 10.1021/acs.joc.4c03135
Mainak Banerjee, Abboy Chatterjee, Shaurya Aneja, Amrita Chatterjee
{"title":"Mechanochemical Functionalization of Heterocycles by C–H Activation: An Update","authors":"Mainak Banerjee, Abboy Chatterjee, Shaurya Aneja, Amrita Chatterjee","doi":"10.1021/acs.joc.4c03135","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03135","url":null,"abstract":"The mechanochemical C–H activation of heterocycles presents a sustainable, solvent-free alternative to the traditional solution-phase synthesis. Heterocycles are fundamental molecular scaffolds in medicinal chemistry and drug discovery. This review highlights recent advances in mechanochemical methods for metal-catalyzed and metal-free C–H functionalization/derivatization, including arylation, alkenylation, acylation, borylation, trifluoromethylation, etc., applied across various heterocyclic compounds. Emphasizing green aspects, this synopsis provides a comprehensive overview of mechanochemical innovations, their unique features and advantages, transformative potential for ecofriendly synthesis, and future prospects of sustainability.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143736930","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
Conjugated 1,8 and 1,6 Addition of Bis-Trimethylsilylketene Acetal to Activated p-Quinone Methides via Trifluoromethanesulfonic Anhydride
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-31 DOI: 10.1021/acs.joc.4c02852
Luis J. Benitez-Puebla, Ricardo Ballinas-Indili, Marcos Flores-Alamo, José M. Guevara-Vela, Tomas Rocha-Rinza, Saulo Rosales-Amezcua, Cecilio Alvarez-Toledano
{"title":"Conjugated 1,8 and 1,6 Addition of Bis-Trimethylsilylketene Acetal to Activated p-Quinone Methides via Trifluoromethanesulfonic Anhydride","authors":"Luis J. Benitez-Puebla, Ricardo Ballinas-Indili, Marcos Flores-Alamo, José M. Guevara-Vela, Tomas Rocha-Rinza, Saulo Rosales-Amezcua, Cecilio Alvarez-Toledano","doi":"10.1021/acs.joc.4c02852","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02852","url":null,"abstract":"In this work, we studied the conjugated additions of bis-trimethylsilylacetalketene acetals (bis-TMSKA) to <i>para</i>-quinone methides (<i>p</i>-QMs), which are one of the most explored molecules for the study of conjugated additions and gained significant attention in organic chemistry due to their versatile reactivity, particularly in Michael addition reactions. In this study, trifluoromethanesulfonic anhydride (Tf<sub>2</sub>O) was used as an activating agent for <i>p</i>-QMs, aiming to achieve 1,6-Michael addition products and the least reported 1,8-Michael addition with pyridine substituents. The reactivity of <i>p</i>-QMs derived from pyridine demonstrated distinct reaction pathways, leading to the formation of δ and γ lactones. The investigation also involved synthesizing a 1-indanone derived from the carboxylic acids obtained from the 1,6-addition.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"53 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143736932","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
Total Syntheses of Uvarindoles A and B, (±)-Pseudophrynaminol, and (±)-Pseudophrynamines 272A and 270 via Dearomative Indole Alkylation
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-31 DOI: 10.1021/acs.joc.5c00062
Raju Chouhan, Sajal Kumar Das
{"title":"Total Syntheses of Uvarindoles A and B, (±)-Pseudophrynaminol, and (±)-Pseudophrynamines 272A and 270 via Dearomative Indole Alkylation","authors":"Raju Chouhan, Sajal Kumar Das","doi":"10.1021/acs.joc.5c00062","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00062","url":null,"abstract":"Herein, we report the first total synthesis of alkaloid uvarindole B with an overall yield of 49% over five steps via double C3-alkylation of 5-bromoindole, Plancher rearrangement, and Negishi coupling as the key steps. We also disclose short total syntheses of uvarindole A, pseudophrynaminol, and pseudophrynamines 272A and 270 via dearomative indole alkylation.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"31 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143736933","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
首页 上一页 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