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Copper-Catalyzed One-Pot Functionalization of Styrenes: Application toward Pharmaceutically Relevant Phenylethylamine Triazole Scaffolds 铜催化苯乙烯的一锅功能化：在药学相关苯乙胺三唑支架中的应用
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-09-15 DOI: 10.1021/acs.joc.5c01782
Timothy A. Hilton, Thomas M. Richardson, Aidan P. McKay, Allan J. B. Watson
{"title":"Copper-Catalyzed One-Pot Functionalization of Styrenes: Application toward Pharmaceutically Relevant Phenylethylamine Triazole Scaffolds","authors":"Timothy A. Hilton, Thomas M. Richardson, Aidan P. McKay, Allan J. B. Watson","doi":"10.1021/acs.joc.5c01782","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01782","url":null,"abstract":"A Cu-catalyzed, one-pot synthesis of 1,2,3-triazolyl phenylethylamine scaffolds is reported. This method utilizes a single copper catalyst to promote aziridination via nitrene addition, ring-opening with azide, and copper-catalyzed azide–alkyne cycloaddition to afford 1,4-disubstituted 1,2,3-triazole phenylethylamine scaffolds. The utility of this process is demonstrated in the synthesis of pharmaceutically relevant cores from simple styrene motifs.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"24 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145059587","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-Mediated Divergent Difunctionalization of gem-Difluoroalkenes Using Aryldiazonium Tetrafluoroborates. 用四氟硼酸芳基重氮进行可见光介导的宝石二氟烯烃发散双官能化。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-09-15 DOI: 10.1021/acs.joc.5c01811
Ming Zheng,Cheng-Wei Zhang,Lu-Yao Qiao,Gang Qi
{"title":"Visible-Light-Mediated Divergent Difunctionalization of gem-Difluoroalkenes Using Aryldiazonium Tetrafluoroborates.","authors":"Ming Zheng,Cheng-Wei Zhang,Lu-Yao Qiao,Gang Qi","doi":"10.1021/acs.joc.5c01811","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01811","url":null,"abstract":"Functionalization of fluoro synthons is an efficient way to construct highly functionalized organofluorine compounds. However, the direct synthesis of α,α-difluoromethyl sulfones from readily accessible gem-difluoroalkenes remains underexplored. This study reports a photocatalytic strategy for the divergent difunctionalization of gem-difluoroalkenes, employing sodium metabisulfite and aryldiazonium tetrafluoroborates. A series of β-hydroxy, β-alkoxy, and β-formyloxy sulfones was obtained in moderate to excellent yields. Furthermore, β-hydroxy and β-alkoxy trichloromethyl compounds can also be synthesized using chloroform as the solvent.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"45 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145059002","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
Palladium-Catalyzed Heteroannulation of Bdan-Capped Alkynes: Rapid Access to Complex Indole Scaffolds 钯催化bdan包盖炔的杂环反应：快速获得复合吲哚支架
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-09-15 DOI: 10.1021/acs.joc.5c01781
Dean D. Roberts, John M. Halford-McGuff, Marek Varga, Aidan P. McKay, Allan J. B. Watson
{"title":"Palladium-Catalyzed Heteroannulation of Bdan-Capped Alkynes: Rapid Access to Complex Indole Scaffolds","authors":"Dean D. Roberts, John M. Halford-McGuff, Marek Varga, Aidan P. McKay, Allan J. B. Watson","doi":"10.1021/acs.joc.5c01781","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01781","url":null,"abstract":"We report the synthesis of 2-indolylboramides via a palladium (Pd)-catalyzed heteroannulation of 2-iodoaniline derivatives and Bdan-capped alkynes (Bdan, 1,8-diaminonaphthalene boronamide). The process is highly regioselective, affording a diverse range of C2-borylated indoles. The synthetic utility of the process is demonstrated through the concise synthesis of the Tetradium alkaloid skeleton.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"70 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145059588","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
S-Benzylation of Sulfenamides with Tertiary Amine Using Methyl Propiolate as a Bifunctional Additive 以丙酸甲酯为双官能团添加剂的亚砜酰胺与叔胺的s -苄基化反应
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-09-15 DOI: 10.1021/acs.joc.5c01561
Wentong Liu, Siyan Qiu, Ruiyang Jin, Liliang Huang, Junhai Huang, Huangdi Feng
{"title":"S-Benzylation of Sulfenamides with Tertiary Amine Using Methyl Propiolate as a Bifunctional Additive","authors":"Wentong Liu, Siyan Qiu, Ruiyang Jin, Liliang Huang, Junhai Huang, Huangdi Feng","doi":"10.1021/acs.joc.5c01561","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01561","url":null,"abstract":"Sulfilimines serve as key intermediates in the synthesis of pharmacologically and agriculturally relevant motifs. We herein report a practical and efficient protocol for the synthesis of sulfilimines via deaminative sulfur benzylation without the addition of a metal catalyst and a base. In the reaction, employing methyl propionate as a bifunctional reagent to activate the amino and sulfenamide groups enables the chemoselective coupling of various sulfenamides with tertiary amines, delivering the target products in high yield with excellent selectivity.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"78 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145059590","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
Solvent Effects on C-H Abstraction by Hydroperoxyl Radicals: Implication for Antioxidant Strategies. 过氧化氢自由基萃取碳氢的溶剂效应：对抗氧化策略的启示。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-09-15 DOI: 10.1021/acs.joc.5c01140
Andrea Baschieri,Zongxin Jin,Greta Tödtmann,Gino A DiLabio,Riccardo Amorati
{"title":"Solvent Effects on C-H Abstraction by Hydroperoxyl Radicals: Implication for Antioxidant Strategies.","authors":"Andrea Baschieri,Zongxin Jin,Greta Tödtmann,Gino A DiLabio,Riccardo Amorati","doi":"10.1021/acs.joc.5c01140","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01140","url":null,"abstract":"Kinetic solvent effects (KSE) on hydrogen atom transfer (HAT) reactions play a pivotal role in processes such as photoredox catalysis, electrochemical synthesis, and antioxidant defense. While general principles of KSE are well established, the influence of solvent-radical interactions on the reactivity of the hydroperoxyl radical (HOO•) remains largely uncharacterized. Here, we examine the effects of noncovalent interactions and acid-base equilibria on HOO• reactivity, using the autoxidation of 1,4-cyclohexadiene (CHD) as convenient HOO• source in chlorobenzene (PhCl) or acetonitrile solutions containing cosolvents (S) with varying hydrogen bond acceptor basicities (β2H). Equilibrium (KS) and CHD + HOO• (kpS) rate constants in PhCl were determined for cosolvents including MeOH, MeCN, DMSO, pyridine, and DABCO. As β2H increased from 0.41 (MeOH) to ∼0.70 (DABCO), KS increased from 50 to 3 × 106 M-1, while kpS decreased from 90 to 0.1 M-1 s-1. MeCN (β2H = 0.44) gave KS = 70 M-1 and kpS = 130 M-1 s-1. For DMSO (β2H = 0.78) and pyridine (β2H = 0.62) KS values were 2.0 × 103 and 3 × 105 M-1, respectively, with corresponding kpS values of 20 and 5 M-1 s-1. The observed KS values show a qualitative correlation with the solvent β2H values of the solvents. Moreover, the calculated α2H values for HOO• in nonbasic cosolvents (MeOH, MeCN, DMSO) cluster around 0.87 ± 0.07, consistent with prior estimates. Experiments in MeCN solution suggest HOO• deprotonation with alkylamines, and the pKa of HOO• is estimated as 18-19. These findings provide mechanistic insight into HOO• reactivity in complex media and suggest new strategies for modulating oxidative radical chemistry in both synthetic and biological contexts.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"52 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145059001","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
Photoredox Catalyzed Cyclization of Enaminones/Ketene N,S-Acetals with β-Ketodinitriles to Access Polysubstituted Pyrroles. 烯胺酮/烯酮N， s -缩醛与β-酮二腈的光氧化还原催化环化制备多取代吡咯。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-09-14 DOI: 10.1021/acs.joc.5c01759
Anup Kumar Sharma,Pratima Singh,Krishna Nand Singh
{"title":"Photoredox Catalyzed Cyclization of Enaminones/Ketene N,S-Acetals with β-Ketodinitriles to Access Polysubstituted Pyrroles.","authors":"Anup Kumar Sharma,Pratima Singh,Krishna Nand Singh","doi":"10.1021/acs.joc.5c01759","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01759","url":null,"abstract":"A facile synthesis of polyfunctionalized pyrroles has been explored via photoredox cascade cyclization of enaminones/ketene N,S-acetals with β-ketodinitriles using eosin Y, CuI, and Ag2CO3 in acetonitrile under blue LED irradiation at room temperature. The present report offers an efficient and straightforward approach to pyrrole-3-carboxylic acids and pyrrole-3-carboxamides with wide substrate scope and functional group tolerance.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"64 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145059005","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
Phenanthrene-Fused BN-Acenaphth(yl)ene: Synthesis, Structures, and Photophysical Studies. 菲融合bn -苊（基）烯：合成、结构和光物理研究。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-09-13 DOI: 10.1021/acs.joc.5c01113
Zhongzan Liu,Jiahao Cui,Yiqing Liu,Huicong Cui,Shunguang Zhang,Xiaoming Wu,Xuguang Liu
{"title":"Phenanthrene-Fused BN-Acenaphth(yl)ene: Synthesis, Structures, and Photophysical Studies.","authors":"Zhongzan Liu,Jiahao Cui,Yiqing Liu,Huicong Cui,Shunguang Zhang,Xiaoming Wu,Xuguang Liu","doi":"10.1021/acs.joc.5c01113","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01113","url":null,"abstract":"Two novel BN-doped CP-PAHs, BN-ANH-TPh and BN-AN-TPh, were synthesized in a straightforward manner. BN-ANH-TPh features a localized C-C bond in the five-membered ring, whereas BN-AN-TPh features a localized C═C bond. Notably, BN-AN-TPh was obtained via the dehydrogenation of BN-ANH-TPh. Both compounds were unambiguously characterized by single-crystal X-ray diffraction analysis. A subtle structural alteration from C-C to C═C bonding resulted in significant modulation of their electronic structures and photophysical properties. Compared to BN-ANH-TPh, BN-AN-TPh exhibits lower LUMO and HOMO energy levels, accompanied by a narrower HOMO-LUMO energy gap. BN-AN-TPh exhibits red-shifted absorption and emission spectra relative to those of BN-ANH-TPh. Both compounds emit strongly in solution, with quantum yields of 73% and 71%, respectively. Furthermore, organic light-emitting diodes (OLEDs) were fabricated by using BN-AN-TPh and BN-ANH-TPh as emissive layers. The OLED device based on BN-AN-TPh achieved a maximum current efficiency of 2.41 cd/A and a maximum luminance of 1556 cd/m2.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"36 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145043538","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 Maleimide Derivatives and Benzo[1,4]oxetane Derivatives: a Modification Method of Amine-Containing Pharmaceuticals. 马来酰亚胺衍生物及苯并[1,4]氧烷衍生物的合成：含胺类药物的改性方法
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-09-13 DOI: 10.1021/acs.joc.5c01519
Lu Yin,Meitian Fu,Sihan Zhao,Qiong Wu,Ruize Jiang,Chao Huang
{"title":"Synthesis of Maleimide Derivatives and Benzo[1,4]oxetane Derivatives: a Modification Method of Amine-Containing Pharmaceuticals.","authors":"Lu Yin,Meitian Fu,Sihan Zhao,Qiong Wu,Ruize Jiang,Chao Huang","doi":"10.1021/acs.joc.5c01519","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01519","url":null,"abstract":"Maleimide-modified drug molecules can improve the stability and selective release of drugs. This study developed an easy-to-operate, mild, and safe synthetic drug-molecule modification strategy. This strategy employs the easily substituted characteristics of the substrate aminomaleimide and various amine-containing molecules under catalyst-free conditions. This method is suitable for various types of primary amines and secondary amines. When reacting with N-methylbenzylamine, benzo[1,4]oxazepane derivatives can be obtained by temperature adjustment. At the same time, the method has good tolerance for substrate functional groups, and 7 maleimide-modified drug molecular fragments were obtained in high yield (80-85%). This article has confirmed that the drug molecules modified by this method still have active reaction sites and can be further modified.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"72 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145043540","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-Induced Radical Relay Trifluoromethylation/Cyclization of N-Cyanamide with Internal Alkenes: Access to Trifluoromethylated Polycyclic Quinazolinones. 可见光诱导的含内烯烃的n -氰酰胺自由基接力三氟甲基化/环化：获得三氟甲基化多环喹唑啉酮。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-09-12 DOI: 10.1021/acs.joc.5c01384
Yuxiu Zhou,Yuanyuan Ren,Ke-Hu Wang,Junjiao Wang,Danfeng Huang,Yulai Hu
{"title":"Visible-Light-Induced Radical Relay Trifluoromethylation/Cyclization of N-Cyanamide with Internal Alkenes: Access to Trifluoromethylated Polycyclic Quinazolinones.","authors":"Yuxiu Zhou,Yuanyuan Ren,Ke-Hu Wang,Junjiao Wang,Danfeng Huang,Yulai Hu","doi":"10.1021/acs.joc.5c01384","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01384","url":null,"abstract":"A visible-light-induced radical relay trifluoromethylation/cyclization reaction between N-cyano-N-isopentenyl arylamide or (E)-N-cinnamyl-N-cyanoarylamide with CF3Br has been developed, affording trifluoromethylated dihydropyrroloquinazolinone derivatives in good yields. A key feature of this method is the regioselective addition of the trifluoromethyl radical to the internal C=C bond of N-cyano-N-isopentenyl arylamides and (E)-N-cinnamyl-N-cyanoarylamides, which directly incorporates a trifluoromethyl group into the pyrrolidine ring of the dihydropyrroloquinazolinones. Mechanistic studies suggest a radical-mediated pathway. The broad substrate scope, excellent functional group tolerance, and use of green energy are expected to enhance its potential applications in pharmaceutical chemistry.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"75 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145036086","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
Iron-Catalyzed Carboxylation of Pyridylphosphonium Salts with CO2. 铁催化吡啶基磷盐与CO2的羧化反应。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-09-12 DOI: 10.1021/acs.joc.5c01797
Shibiao Tang,Bin Li,Baiquan Wang
{"title":"Iron-Catalyzed Carboxylation of Pyridylphosphonium Salts with CO2.","authors":"Shibiao Tang,Bin Li,Baiquan Wang","doi":"10.1021/acs.joc.5c01797","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01797","url":null,"abstract":"Iron is the most abundant transition metal on earth and exhibits the lowest toxicity. However, the iron-catalyzed carboxylation reaction utilizing CO2 remains significantly underexplored. Here we report an efficient iron-catalyzed carboxylation of pyridylphosphonium salts with CO2, which enables the synthesis of a variety of high value-added isoniazid derivatives. This reaction demonstrates excellent tolerance for a wide range of functional groups and possesses high synthetic practicality. The primary catalytic cycle in this reaction may involve an Fe(0)-Fe(I)-Fe(II)-Fe(0) redox sequence.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145043547","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
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