Journal of Organic Chemistry最新文献_第2页

Bifunctional Ionic Liquids Induced Electrochemical C-H Arylation of Quinoxalin(on)es with Aryltriazenes. 双功能离子液体诱导喹啉与芳基三氮烯的C-H电化学芳基化反应。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-05-15 DOI: 10.1021/acs.joc.5c00460

Chenyu Li,Wei Xu,Bin Wang,Ziren Chen,Yu Xia,Shaofeng Wu,Weiwei Jin,Chenjiang Liu,Yonghong Zhang

引用次数: 0

Electrophilic (Hetero)Arene C-H Nitration by Ferric Nitrate Nonahydrate in Hexafluoroisopropanol. 非水合硝酸铁在六氟异丙醇中硝化亲电（杂）芳烃的研究。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-05-15 DOI: 10.1021/acs.joc.5c00137

Yuzhu Zheng,Zongyi Liu,Zhaobo Ying,Youwei Xie

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A One-Pot Relay Sc(III)/Base-Promoted Addition/Cyclization of 1-(o-Aminophenyl)prop-2-Ynols and S/C Nucleophiles: Synthesis of 3-Sulfenylindole and 3-Arylindole Derivatives. 1-（邻氨基苯基）2-丙炔醇和S/C亲核试剂的一锅接力Sc(III)/碱促进加成/环化：3-亚砜酰吲哚和3-芳酰吲哚衍生物的合成。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-05-15 DOI: 10.1021/acs.joc.5c00182

Chang He,Xiao-Han Qiu,Yi-Feng Lin,Ming Bian,Hui-Yu Chen,Yu-Ning Gao,Zhen-Jiang Liu

引用次数: 0

Quantification of the H-Bond-Donating Ability of Trifluoromethyl Ketone Hydrates Using a Colorimetric Sensor 用比色传感器定量测定三氟甲基酮水合物的给氢键能力

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-05-15 DOI: 10.1021/acs.joc.4c03046

Cameron B. Berlin, Emily Sidlow, Chris Zheng, Marisa C. Kozlowski

引用次数: 0

Computational Rational Design of Bridgehead Nitrogen Heterocyclic Azobenzene Photoswitches. 桥头堡氮杂环偶氮光开关的计算合理设计。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-05-15 DOI: 10.1021/acs.joc.5c00731

Dunja Pupavac,Andrea M Nikolić,John-Paul Webster,Theodore P Curtis,Boban And Elković,Timothy R Newhouse,Igor M Opsenica

{"title":"Computational Rational Design of Bridgehead Nitrogen Heterocyclic Azobenzene Photoswitches.","authors":"Dunja Pupavac,Andrea M Nikolić,John-Paul Webster,Theodore P Curtis,Boban And Elković,Timothy R Newhouse,Igor M Opsenica","doi":"10.1021/acs.joc.5c00731","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00731","url":null,"abstract":"Azobenzenes are proven to be one of the most successful molecular photoswitches applied across different fields such as organic chemistry, material science, cosmetics, and pharmaceuticals. Such a widespread implementation is possible because of their photochromic properties contingent upon the substitution pattern and aryl-core nature. In recent endeavors of molecular design, replacing one or both phenyl rings with heteroaromatics turned out to be a good strategy to access compounds with improved photoswitching properties, as well as to expand molecular diversity. One of the challenges related to the design of new azobenzene photoswitches is that it often includes the synthesis of large libraries of compounds due to limited methods for prediction of their properties. Herein, we present a computationally driven workflow for the design and synthesis of a novel class of azobenzene photoswitches, heteroaryl azobenzenes with N-bridgehead heterocycles─pyrazolo[1,5-a]pyrimidine and 1,2,4-triazolo[1,5-a]pyrimidine. A small library of heteroaryl photoswitches was synthesized, and their photochemical properties were evaluated. Subsequently, these results were used to validate a computational approach, which included the in silico evaluation of a large library of designed photoswitch candidates leading to the synthesis of a new photoswitch with improved spectral properties, red-shifted λmax values.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"80 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143991993","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

Organocatalytic Synthesis of Spiro-Bridged Heterocyclic Compounds via a Chemoselective Vinylogous Michael/Cyclization/Rearrangement Sequence. 通过化学选择性链化Michael/环化/重排序列的有机催化合成螺旋桥接杂环化合物。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-05-15 DOI: 10.1021/acs.joc.5c00443

I-Ting Chen,Hsuan Lin,Jeng-Liang Han

引用次数: 0

Photoredox Iron-Catalyzed Decarboxylative Radical Cyclization for the Synthesis of Oxindoles and Chroman-4-ones. 光氧化还原铁催化脱羧自由基环化合成氧吲哚和铬-4-酮。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-05-15 DOI: 10.1021/acs.joc.5c00669

Shaoyang Han,Litao Liu,Jianqing Meng,Meichao Li,Qun Cao,Zhenlu Shen

引用次数: 0

Why Does Rh Prefer [4 + 1] while Pd Prefer [4 + 4 + 1] Mode in Carbocyclization of Vinylallene with CO? Unveiling Nickel’s Potential for Expanding the Scope Beyond Pd 为什么在乙烯烯与CO的碳环化过程中Rh倾向于[4 + 1]而Pd倾向于[4 + 4 + 1]模式？揭示镍的潜力，以扩大范围超越钯

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-05-14 DOI: 10.1021/acs.joc.5c00585

Sheetal Ranaut, Shivnath Mazumder

{"title":"Why Does Rh Prefer [4 + 1] while Pd Prefer [4 + 4 + 1] Mode in Carbocyclization of Vinylallene with CO? Unveiling Nickel’s Potential for Expanding the Scope Beyond Pd","authors":"Sheetal Ranaut, Shivnath Mazumder","doi":"10.1021/acs.joc.5c00585","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00585","url":null,"abstract":"Rhodium(I) promotes a [4 + 1] assembly mode with a vinylallene substrate and CO, leading to the formation of a five-membered ring structure. In striking contrast, palladium(0) catalyzes a more complex [4 + 4 + 1] mode leading to a nine-membered cyclic ketone. The underlying mechanisms that govern this contrast in assembly modes remain unclear, even in today’s date, presenting a major challenge to the further development of efficient reactions. Our computational study reveals that Rh adopts a square pyramidal geometry with CO. This is in contrast to Pd, which prefers a trigonal planar geometry. A stronger metal–CO interaction is detected in Rh than in a Pd intermediate, making the [4 + 1] mode more preferable in Rh than in Pd. The transition state for C–C coupling between two vinylallene has a significantly distorted tetrahedral core in the case of Rh, while Pd retains a stable trigonal planar structure, making the [4 + 4 + 1] reaction less favorable in Rh than in Pd. By conceptualizing and transferring the critical features of Pd to Ni systems, we have rationally designed a Ni-catalyzed [4 + 4 + 1] version that combines the desirable reactivity of Pd with the cost-effectiveness and abundance of Ni, aligning with the growing demand for more sustainable and atom-efficient strategies in synthetic organic chemistry.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143945802","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

Reductive Deuteration of Aldehydes/Ketones for the Synthesis of Monodeuterated Phosphinates and Derivatives Using D2O as the Nucleophilic Deuterium Source. 以D2O为亲核氘源合成单氘化膦酸盐及其衍生物的醛/酮还原氘化反应

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-05-14 DOI: 10.1021/acs.joc.5c00235

Xiaochen Niu,Yuanyuan Xie,Hongwei Zhou

引用次数: 0

Photoactivation of Thianthrenium Salts: An Electron-Donor-Acceptor (EDA)-Complex Approach. 硫鎓盐的光活化：电子给体-受体（EDA）复合物方法。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-05-14 DOI: 10.1021/acs.joc.5c00194

Roshan I Patel,Barakha Saxena,Anuj Sharma

{"title":"Photoactivation of Thianthrenium Salts: An Electron-Donor-Acceptor (EDA)-Complex Approach.","authors":"Roshan I Patel,Barakha Saxena,Anuj Sharma","doi":"10.1021/acs.joc.5c00194","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00194","url":null,"abstract":"Thianthrenium salts have emerged as one of the most versatile reagents, gaining significant popularity within the synthetic community for their utility in the construction of C-C and C-X (X = N, O, S, P, halogens) bonds. The use of photoredox and transition metal catalysis with thianthrenium salts for C-C and C-heteroatom bond formation is well established. However, most of these methods require elevated temperatures, expensive catalysts, and ligands under stringent conditions for effective execution. In contrast, the photocatalysis- and transition-metal-free approaches for constructing C-C and C-X bonds using thianthrenium salt derivatives have become increasingly sought after. In this regard, electron-donor-acceptor (EDA)-complex reactions have emerged as a powerful strategy in organic synthesis, eliminating the need for photocatalysts under visible light irradiation. EDA-complex photochemistry exploits the electron-acceptor properties of thianthrenium salts, facilitating the rapid generation of radical intermediates via the C-S bond cleavage. These radical intermediates play a pivotal role in enabling a variety of valuable C-C and C-X formations. In this Perspective, we highlight significant advances in the EDA-complex-mediated reactions involving thianthrenium salts with mechanisms, substrate scope, and limitations for constructing C-C and C-heteroatom bonds. For the sake of brevity, the article is organized into five main sections: (1) Nitrogen-based donor reactions, (2) Oxygen-based donor reactions, (3) Sulfur-based donor reactions, (4) Phosphorus-based donor reactions, and (5) π-based donor reactions, with a focus on C-C, C-S, C-B and C-P bond formations.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143982526","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