Journal of Organic Chemistry最新文献_第2页

Enhanced Cytotoxicity of 10α,9β-Abiraterone Analogues Synthesized via LED Photocatalysis. LED光催化合成的10α，9β-阿比特龙类似物增强细胞毒性。

IF 3.3 2区化学

Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1021/acs.joc.5c00709

Hongping Jiang, Xirong Liu, Chunling Zeng, Jie Tang, Guofang Jiang

引用次数: 0

Acid-Enabled Dearomative Umpolung of 3-Indolylquinones toward C3-Oxygenated Benzofuro[2,3-b]indolines. 3-吲哚基醌对c3 -氧合苯并呋喃[2,3-b]吲哚的酸致脱芳研究

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1021/acs.joc.5c00710

Wenkang Wu,Chenglong Zhu,Yongzheng Zhang,Tingting Yan,Jingyuan Yao,Guanyu Yang,Yingchao Dou

引用次数: 0

Organophotocatalyzed Radical Hydrophosphonylation of Acrylates, α,β-Unsaturated Ketones, Coumarins, Quinoxalinones, and p-Quinone Methides. 有机光催化丙烯酸酯、α、β-不饱和酮、香豆素、喹草胺酮和对醌类化合物的自由基氢膦化。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1021/acs.joc.5c00767

Nisha Rawat,Parashuram Sharma,Seshadri Reddy Nasireddy,Anjul Vilas,Anand Singh

引用次数: 0

Direct, Asymmetric, and Stereodivergent Reactions of N-Azidoacetyl Thioimides with Aromatic Acetals Catalyzed by Chiral Nickel(II) Complexes. An Approach to the Synthesis of syn- and anti-β-Alkoxy-α-amino Acids 手性镍（II）配合物催化n -叠氮乙酰基硫酰亚胺与芳香缩醛的直接、不对称和立体发散反应。合成正、反β-烷氧基-α-氨基酸的方法研究

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1021/acs.joc.5c00390

Miguel Mellado-Hidalgo, Joan Conejos-Jalencas, Saúl F. Teloxa, Andrea Suárez-Herrera, Luke McCall, Anna M. Costa, Pedro Romea, Fèlix Urpí, Gabriel Aullón, Cristina Puigjaner

引用次数: 0

Regiodivergent Annulation Reactions of Chalcones to Indenones and Indanones with C1 Reagents. C1试剂对查尔酮与吲哚酮和吲哚酮的区域发散环化反应。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1021/acs.joc.5c00497

Xinchi Gong,Sunewang R Wang

引用次数: 0

The Form of the HOMA Geometric Aromaticity Index Is Universal and Allows the Design of Electronic and Magnetic Descriptors. HOMA几何芳香性指数的形式具有通用性，可用于设计电子和磁性描述符。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1021/acs.joc.5c00740

Jan Cz Dobrowolski,Sławomir Ostrowski

{"title":"The Form of the HOMA Geometric Aromaticity Index Is Universal and Allows the Design of Electronic and Magnetic Descriptors.","authors":"Jan Cz Dobrowolski,Sławomir Ostrowski","doi":"10.1021/acs.joc.5c00740","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00740","url":null,"abstract":"The HOMA geometrical aromaticity index is unique. It is simple, based on observable bond distances, and can be defined using experimental or computational bond values. Moreover, its mathematical form expresses geometric similarity to the archetypal aromatic benzene. Here, we show that HOMA is simply a kind of mean of the errors squared (MSE). This is why the index is such a good measure of aromaticity. Thus, only a slight modification grounds the HOMA index on electronic or magnetic properties, producing an electronic or magnetic molecular measure expressing electronic or magnetic similarity/dissimilarity to benzene. Based on an analysis of over 70 neutral or charged carbocyclic rings, we compare the HOMA indices based on bond distances, selected electron density properties in bond or ring critical points, chemical shifts, and spin-spin coupling constants. We conclude that using electronic and magnetic variables discloses separate trends that are invisible if CC bond lengths are used. Such new HOMA indices can be used to study different facets of aromaticity and as more general molecular structure descriptors.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"43 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144311329","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 Copper-Catalyzed Alkene Aminofluorination and Rational Design of a Metal-Free Strategy. 铜催化烯烃胺氟化反应机理及无金属策略的合理设计。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-06-16 DOI: 10.1021/acs.joc.5c00672

Yihao Zhang,Shuqi Zhang,Jiying Xu,Shuhao Ge,Shipeng Sun,Gernot Frenking,Lili Zhao

{"title":"Mechanistic Insights into Copper-Catalyzed Alkene Aminofluorination and Rational Design of a Metal-Free Strategy.","authors":"Yihao Zhang,Shuqi Zhang,Jiying Xu,Shuhao Ge,Shipeng Sun,Gernot Frenking,Lili Zhao","doi":"10.1021/acs.joc.5c00672","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00672","url":null,"abstract":"The β-fluoroalkylamine motif holds great value in drug development due to the unique properties imparted by fluorine incorporation. Currently, the most promising way for accessing this motif involves alkene aminofluorination, which heavily relies on transition-metal (TM) catalysts. Inspired by a control experiment reported in a related previous study, we herein rationally design a novel metal-free strategy for alkene aminofluorinations. Quantum chemical calculations revealed that the desired aminofluorination pathway (ΔΔG‡ = 38.5 kcal/mol) is inherently less favorable than the competing alkene polymerization side reaction (ΔΔG‡ = 18.7 kcal/mol). To overcome this challenge, we utilized the Energy Decomposition Analysis with Natural Orbitals for Chemical Valence (EDA-NOCV) method to gain insight into various electrophilic amination reagents and found that N-halogeno-amines with weakened N-X bonds (X = F, Cl, Br, I) could be promising candidates for system optimization. Among these, N-I-amines proved most effective, steering the reaction toward aminofluorination. Further reaction kinetics simulations confirmed that the optimized system can achieve an 80% yield of β-fluoroalkylamines within 3 h at 343 K, which is comparable to experimentally reported transition metal-catalyzed system. Therefore, this study introduces a sustainable, metal-free approach for alkene aminofluorination via a radical chain mechanism, offering a greener alternative to the traditional TM-catalyzed process.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144295734","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

Binuclear Copper-Catalyzed Enantioselective C,N-Dipolar (3 + 2) Cycloadditions: Mechanistic Insights and Selectivity Control via DFT Analysis. 双核铜催化的对映选择性C， n偶极（3 + 2）环加成：通过DFT分析的机理见解和选择性控制。

IF 3.3 2区化学

Journal of Organic Chemistry Pub Date : 2025-06-16 DOI: 10.1021/acs.joc.5c00745

Yu Wang, Linxing Zhang, Jia Zhou, Lijuan Song

{"title":"Binuclear Copper-Catalyzed Enantioselective C,N-Dipolar (3 + 2) Cycloadditions: Mechanistic Insights and Selectivity Control via DFT Analysis.","authors":"Yu Wang, Linxing Zhang, Jia Zhou, Lijuan Song","doi":"10.1021/acs.joc.5c00745","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00745","url":null,"abstract":"2-Aminoallyl cations serve as highly versatile intermediates in organic synthesis. Their cycloaddition with unsaturated compounds provides an efficient strategy for the construction of heterocycles, which are key structural motifs found in a wide range of natural products, bioactive molecules, and agrochemicals. The mechanism and enantioselectivity of the C,N-dipolar (3 + 2) cycloaddition of 2-aminoallyl cations with indoles have been investigated using density functional theory (DFT). We proposed that binuclear copper-assisted decarboxylation produces the 2-aminoallyl cation from ethynyl methylene cyclic carbamates (EMCCs), which then undergoes an enantioselective (3 + 2) cycloaddition reaction with indoles to yield the final product. Our results indicate that the concerted mechanism is more favorable than the stepwise mechanism. The concerted mechanism involves asynchronous bond formation processes. The enantioselectivity is predominantly governed by the distortion energy. The atomic dipole moment corrected Hirshfeld (ADCH) charge indicates that the regioselectivity is determined by the charge matching principle. The electron-poor carbon (C4: + 0.033) of the indole preferentially reacts with the nitrogen atom (N2: - 1.010) of the dipolar intermediate, leading to the formation of the major product. To validate the binuclear activation hypothesis, we computationally rationalized that chiral benzo[c]cinnoline-dioxazoline-supported binuclear copper catalysts ([L1(Cu)2]2+) exhibit enhanced catalytic efficiency for the C,N-dipolar (3 + 2) cycloaddition reaction.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144309297","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

Synthesis of 3,3-Disubstituted Oxindoles through Cascade Alkylarylation of N-Arylacrylamides with Carboxylic Acids Enabled by Iron Photocatalysis. 铁光催化n -芳基丙烯酰胺与羧酸级联烷基化合成3,3-二取代氧吲哚。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-06-16 DOI: 10.1021/acs.joc.5c00970

Xinran Zhang,Shuxin Yang,Jiaxing Lv,Wanpeng Lu,Yi Bi,Xianhe Fang

引用次数: 0

Nonradical Reactions of p-Benzyne Diradicals. 对苯双自由基的非自由基反应。

IF 3.3 2区化学

Journal of Organic Chemistry Pub Date : 2025-06-16 DOI: 10.1021/acs.joc.5c00517

Charles L Perrin

引用次数: 0