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A Metal-Free Direct Decarboxylative Fluoroacylation of Indole Carboxylic Acids with Fluorinated Acids. 吲哚羧酸与氟化酸的无金属直接脱羧氟化反应。
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-25 DOI: 10.1021/acs.joc.4c01842
Xingxing Zhang,Guangyuan Liu,Xing Sun,Luo-Sheng Wan,Yirong Zhou
{"title":"A Metal-Free Direct Decarboxylative Fluoroacylation of Indole Carboxylic Acids with Fluorinated Acids.","authors":"Xingxing Zhang,Guangyuan Liu,Xing Sun,Luo-Sheng Wan,Yirong Zhou","doi":"10.1021/acs.joc.4c01842","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01842","url":null,"abstract":"A straightforward preparation of diversified fluorinated indol-3-yl ketones was developed by the direct decarboxylative fluoroacylation of indole carboxylic acids. The reaction could be performed on a gram scale under net conditions. Neither a metal catalyst nor an additive was employed. This methodology featured simple reaction conditions, high efficiency, exclusive selectivity, a broad substrate scope, and easy operation, which allowed it to meet the green chemistry requirement of the modern pharmaceutical industry. Control experiments confirmed that a radical process might be involved in the tandem decarboxylative fluoroacylation sequence.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142325237","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
Electrochemical Bromination of Arenes in a 200% Cell. 200% 电池中的烯的电化学溴化。
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-25 DOI: 10.1021/acs.joc.4c01086
Sara Torabi,Mahdi Jamshidi,Gerhard Hilt
{"title":"Electrochemical Bromination of Arenes in a 200% Cell.","authors":"Sara Torabi,Mahdi Jamshidi,Gerhard Hilt","doi":"10.1021/acs.joc.4c01086","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01086","url":null,"abstract":"Herein, we describe the investigation of electrochemical bromination of electron-rich arenes in a 200% cell. For this application, at first, the influence of an excess of supporting electrolyte (Bu4NBr) on chemical bromination was investigated. The application of >4.0 equiv of Bu4NBr proved to enhance the regioselectivity of the bromination process for O- and N-substituted arenes considerably. The linear paired electrolysis was then optimized upon these insights, and a number of electron-rich arenes could be brominated in high yields with excellent regioselectivity. The use of O2 as a sacrificial starting material in combination with 2-ethylanthraquinone as a catalyst leads to the enhanced formation of H2O2 at the cathode, resulting in current efficiencies >150% for a considerable number of examples.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142321241","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
Correction to “Structure–Activity Relationship Studies of the Peptide Antibiotic Clovibactin” 对 "多肽抗生素 Clovibactin 的结构-活性关系研究 "的更正
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-25 DOI: 10.1021/acs.joc.4c02243
Jackson E. H. Brunicardi, James H. Griffin, Michael J. Ferracane, Adam G. Kreutzer, Jeramiah Small, Ana-Teresa Mendoza, Joseph W. Ziller, James S. Nowick
{"title":"Correction to “Structure–Activity Relationship Studies of the Peptide Antibiotic Clovibactin”","authors":"Jackson E. H. Brunicardi, James H. Griffin, Michael J. Ferracane, Adam G. Kreutzer, Jeramiah Small, Ana-Teresa Mendoza, Joseph W. Ziller, James S. Nowick","doi":"10.1021/acs.joc.4c02243","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02243","url":null,"abstract":"The Protein Data Bank (PDB) code for <i>N</i>-Me-<span>d</span>-Leu<sub>2</sub>-<span>d</span>-Thr<sub>5</sub>-clovibactin is 9BIC. 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":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142317777","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
Carbene-Catalyzed [3 + 3] Annulation of Enals and Vinyl Sulfoxonium Ylides 碳催化烯醛和乙烯基锍酰化物的 [3 + 3] 嵌合反应
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-25 DOI: 10.1021/acs.joc.4c01587
Siru Feng, Hailong Zhang, Jinhua Liu, Dongping Shi, Weiqi Yang, Haibin Zhu, Xiaoxiang Zhang, Zhenqian Fu
{"title":"Carbene-Catalyzed [3 + 3] Annulation of Enals and Vinyl Sulfoxonium Ylides","authors":"Siru Feng, Hailong Zhang, Jinhua Liu, Dongping Shi, Weiqi Yang, Haibin Zhu, Xiaoxiang Zhang, Zhenqian Fu","doi":"10.1021/acs.joc.4c01587","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01587","url":null,"abstract":"Carbene-catalyzed [3 + 3] annulation of enals and vinyl sulfoxonium ylides has been demonstrated. This method efficiently synthesizes a range of 2-sulfenylidene-3-cyclohexen-1-ones with high atom economy. Notably, the presence of the sulfoxonium ylide moiety in the obtained products significantly enhances their potential for further synthetic transformations.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142321886","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
Structure-Directed Quaternary Ammonium Hydroxide Resins: High-Performance Heterogeneous Base Catalysts for Continuous-Flow Carbon–Carbon Bond-Forming Reactions 结构定向季铵氢氧化物树脂：用于连续流碳-碳键形成反应的高性能异构碱催化剂
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-25 DOI: 10.1021/acs.joc.4c01506
Haruro Ishitani, Yuichi Furiya, Akihiro Ide, Shu̅ Kobayashi
{"title":"Structure-Directed Quaternary Ammonium Hydroxide Resins: High-Performance Heterogeneous Base Catalysts for Continuous-Flow Carbon–Carbon Bond-Forming Reactions","authors":"Haruro Ishitani, Yuichi Furiya, Akihiro Ide, Shu̅ Kobayashi","doi":"10.1021/acs.joc.4c01506","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01506","url":null,"abstract":"Quaternary ammonium hydroxide resins are widely recognized for their effectiveness as immobilized bases and are frequently utilized as commodity chemicals for anion-exchange applications. However, despite their accessibility, chemically controlling their properties has proven challenging, hindering research and development efforts toward their use as solid base catalysts. This study investigates the synthetic factors that are crucial for achieving high functional performance in polystyrene resins. Using commercially available resin as a benchmark and the continuous-flow Henry reaction as a model system, we explore and evaluate newly synthesized resin catalysts to maximize their basic catalytic activity.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142317776","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 Transfer Hydrogenation of Allylic Alcohols with Isopropanol 铁催化异丙醇与烯丙基醇的转移加氢反应
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-25 DOI: 10.1021/acs.joc.4c01701
Md Abdul Bari, Salma A. Elsherbeni, Tahir Maqbool, Daniel E. Latham, Edward B. Gushlow, Emily J. Harper, Louis C. Morrill
{"title":"Iron-Catalyzed Transfer Hydrogenation of Allylic Alcohols with Isopropanol","authors":"Md Abdul Bari, Salma A. Elsherbeni, Tahir Maqbool, Daniel E. Latham, Edward B. Gushlow, Emily J. Harper, Louis C. Morrill","doi":"10.1021/acs.joc.4c01701","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01701","url":null,"abstract":"Herein, we report an iron-catalyzed transfer hydrogenation of allylic alcohols. The operationally simple protocol employs a well-defined bench stable (cyclopentadienone)iron(0) carbonyl complex as a precatalyst in combination with K<sub>2</sub>CO<sub>3</sub> (4 mol %) and isopropanol as the hydrogen donor. A diverse range of allylic alcohols undergo transfer hydrogenation to form the corresponding alcohols in good yields (33 examples, ≤83% isolated yield). The scope and limitations of the method have been investigated, and experiments that shed light on the reaction mechanism have been conducted.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142317775","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
Silver-Catalyzed 1,2-Thiosulfonylation of Alkenes: Development of a Nucleophilic d3-Methylthiolating Reagent 银催化烯烃的 1,2-硫代磺酰化反应：开发亲核 d3-甲硫基试剂
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-25 DOI: 10.1021/acs.joc.4c01787
Zhiyong Ye, Yan Zhang, Guofang Guo, Xinxin Shao, Ji-Rong Wu
{"title":"Silver-Catalyzed 1,2-Thiosulfonylation of Alkenes: Development of a Nucleophilic d3-Methylthiolating Reagent","authors":"Zhiyong Ye, Yan Zhang, Guofang Guo, Xinxin Shao, Ji-Rong Wu","doi":"10.1021/acs.joc.4c01787","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01787","url":null,"abstract":"Development of robust <i>d</i><sub>3</sub>-methylthiolating reagents represents an attractive synthetic method to access deuterated molecules in the field of drug discovery. Here, we report a straightforward strategy to prepare electrophilic <i>S</i>-methyl-<i>d</i><sub>3</sub> arylsulfonothioates in one-step without column purification. These reagents exhibit good radical reactivity toward silver-catalyzed vicinal thiosulfonylation of alkenes or 1,6-enynes on water. As a result, simultaneous incorporation of both SCD<sub>3</sub> and ArSO<sub>2</sub> units into unsaturated carbon–carbon bonds with 100% atom economy has been established. Moreover, the ATRA adducts with &gt;99% D incorporation can serve as nucleophilic <i>d</i><sub>3</sub>-methylthiolating synthons via retro-Michael addition under mild basic conditions, providing a good alternative in trideuteromethylthiolating alkyl iodides to access corresponding trideuteromethyl sulfides with high efficiency.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142321884","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
A Dual CQD-Catalysis and H-Bond Acceptor for Controlling Product Selectivity and Regioselectivity in Symmetric/Unsymmetric Azoxy Arenes 用于控制对称/不对称氮氧烯中产物选择性和区域选择性的双重 CQD 催化和 H 键受体
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-25 DOI: 10.1021/acs.joc.4c00373
Morteza Hasani, Hamid R. Kalhor
{"title":"A Dual CQD-Catalysis and H-Bond Acceptor for Controlling Product Selectivity and Regioselectivity in Symmetric/Unsymmetric Azoxy Arenes","authors":"Morteza Hasani, Hamid R. Kalhor","doi":"10.1021/acs.joc.4c00373","DOIUrl":"https://doi.org/10.1021/acs.joc.4c00373","url":null,"abstract":"Azoxy arenes are valuable compounds in different areas of chemistry, such as organic chemistry, medicinal chemistry, and natural product chemistry. Despite their value, the regioselective synthesis of unsymmetric azoxybenzenes has remained a real challenge in the field. Herein, the product selectivity in oxidative homocoupling of anilines into symmetric azoxybenzenes was first achieved by an asparagine-functionalized CQD catalyst. Subsequently, in the cross-coupling of anilines into the unsymmetric azoxybenzenes via an ortho H-bond acceptor (HBA) on one of the coupling anilines, the regioselectivity was effectively controlled. It was demonstrated that ortho-HBA could mechanistically establish a six-membered intramolecular hydrogen-bonded ring on an <i>N</i>,<i>N</i>′-dihydroxy intermediate. The formed hydrogen bond makes the nearby nitrogen eminently suitable for the slow dehydration step. As a result, the functional oxygen of the azoxy compound is placed far from the HBA. The o-HBA mechanism also controls the regioselectivity ratio in which 1:0 (with an intramolecular H-bonded hexagonal ring), 2:1 (with an intramolecular H-bonded pentagonal ring), and 1:1 (without an ortho-HBA) isomeric mixtures could be achieved. The HBA mechanism was exploited by different substituted anilines, and various unsymmetric azoxybenzenes were synthesized. Finally, with the aid of mechanistic studies, a plausible mechanism for the reaction was proposed.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142317772","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
Copper-Catalyzed Oxidative Synthesis of 3-Aryl-5-fluoroalkyl-1,3,4-oxadiazol-2(3H)-ones Using Perfluorocarboxylic Anhydride as a Reagent 以全氟羧酸酐为试剂，铜催化氧化合成 3-芳基-5-氟烷基-1,3,4-恶二唑-2(3H)-酮
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-25 DOI: 10.1021/acs.joc.4c01900
Jiaqing Lu, Shouxiong Chen, Minze Wu, Hongshan Yin, Xi Lin, Wei Wu, Zhiqiang Weng
{"title":"Copper-Catalyzed Oxidative Synthesis of 3-Aryl-5-fluoroalkyl-1,3,4-oxadiazol-2(3H)-ones Using Perfluorocarboxylic Anhydride as a Reagent","authors":"Jiaqing Lu, Shouxiong Chen, Minze Wu, Hongshan Yin, Xi Lin, Wei Wu, Zhiqiang Weng","doi":"10.1021/acs.joc.4c01900","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01900","url":null,"abstract":"A copper-catalyzed oxidative annulation of sydnones with perfluorocarboxylic anhydride for the synthesis of 3-aryl-5-fluoroalkyl-1,3,4-oxadiazol-2(3<i>H</i>)-ones is developed. A diverse array of 3-aryl-5-fluoroalkyl-1,3,4-oxadiazol-2(3<i>H</i>)-ones are prepared with good yields (&gt;73 examples, yields up to 95%). The synthetic utility of the developed protocol was demonstrated by gram-scale synthesis, and the synthetic transformation to 1,2,4-triazol-3-one products. A mechanistic study suggests that the reaction proceeds via the extrusion of carbon dioxide to generate the hydrazide intermediate, which then undergoes intramolecular cyclization and oxidation.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142317774","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 and Performance Evaluation of Zwitterionic C-N Bonded Triazole-Tetrazole-Based Primary Explosives. 以三唑-四唑为基础的 C-N 键齐聚物原生爆炸物的合成与性能评估。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-24 DOI: 10.1021/acs.joc.4c01434
Shreyasi Banik, Vikas D Ghule, Srinivas Dharavath
{"title":"Synthesis and Performance Evaluation of Zwitterionic C-N Bonded Triazole-Tetrazole-Based Primary Explosives.","authors":"Shreyasi Banik, Vikas D Ghule, Srinivas Dharavath","doi":"10.1021/acs.joc.4c01434","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01434","url":null,"abstract":"<p><p>Developing advanced metal-free nitrogen-enriched primary explosives is challenging due to the inherent risks associated with their synthesis and handling. However, there is an urgent need to develop novel lead-free, nitrogen-rich primary explosives that offer balanced energetic properties. C-N bonded bicyclic compound 3-azido-1-(1<i>H</i>-tetrazol-5-yl)-1<i>H</i>-1,2,4-triazol-5-amine (<b>4</b>), its salts, and 3,5-diazido-1<i>H</i>-1,2,4-triazole (<b>8</b>) were synthesized from inexpensive starting materials resulting in a fine blend of sensitivity and stability. These compounds exhibit high nitrogen content (79.78 to 83.43%), good thermal stability (129-210 °C), excellent detonation performance (VOD: 8592-9361 ms<sup>-1</sup>, DP: 27.1-33.8 GPa), and acceptable sensitivity (IS: 2.5-30 J, FS: 72-288 N). The hot needle tests of compounds <b>4</b> and <b>8</b> exhibit excellent ignition performance. All of the newly synthesized compounds were fully characterized using infrared spectroscopy (IR), high-resolution mass spectroscopy (HRMS), multinuclear magnetic spectroscopy (NMR), elemental analysis (EA), thermogravimetric analysis-differential scanning calorimetry (TGA-DSC), and <b>2</b>, <b>4</b>, and <b>8</b> were confirmed by single-crystal X-ray crystallographic studies. The molecular electrostatic potential (ESP), noncovalent interactions reduced density gradient (NCI-RDG) method, and QTAIM analysis were performed to investigate the intermolecular interactions. Together with promising performance properties, ease of synthesis, and ignitability, they are highly suitable candidates to pave new avenues for future applications.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142306628","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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