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One-Step Realization of Skeleton Editing, gem-Dinitromethyl Functionalization, and Zwitterionization in a Laser-Sensitive 1,3,4-Oxadiazole Energetic Molecule
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-15 DOI: 10.1021/acs.orglett.4c04504
Mingren Fan, Xiu’e Jiang, Ruihui Wang, Linhu Pan, Xiujuan Qi, Siwei Song, Yi Wang, Qinghua Zhang
{"title":"One-Step Realization of Skeleton Editing, gem-Dinitromethyl Functionalization, and Zwitterionization in a Laser-Sensitive 1,3,4-Oxadiazole Energetic Molecule","authors":"Mingren Fan, Xiu’e Jiang, Ruihui Wang, Linhu Pan, Xiujuan Qi, Siwei Song, Yi Wang, Qinghua Zhang","doi":"10.1021/acs.orglett.4c04504","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04504","url":null,"abstract":"The single-atom skeletal editing technology is an efficient method for constructing molecular skeletons, which has broad coverage in synthetic chemistry. However, its potential in the preparation of energetic heterocyclic molecules is grossly underexplored. In this work, an unexpected one-step reaction for the synthesis of novel energetic molecules was discovered which combines single-atom skeletal editing, <i>gem</i>-dinitromethyl functionalization, and zwitterionization in one step. The reaction demonstrates high efficiency while maintaining the characteristics of being mild and facile. The reaction mechanism was verified by experimental evidence and theoretical calculations. This reaction produces a novel energetic molecule (<b>NPX-04</b>) with good laser ignition performance, indicating its promise as a laser-sensitive energetic material.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"37 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142981922","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Photoinduced Cobaloxime-Catalyzed Regio- and Diastereoselective Hydrogen-Evolution C(sp3)–H Phosphorylation of Bicyclo[1.1.0]butanes
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-15 DOI: 10.1021/acs.orglett.4c04702
Peng-Fei Chen, Meng-Yuan Dong, Chun-Yu Han, Dong-Sheng Li, Yang Hong, Fei Xue, Fang Liu, Hong-Ping Deng
{"title":"Photoinduced Cobaloxime-Catalyzed Regio- and Diastereoselective Hydrogen-Evolution C(sp3)–H Phosphorylation of Bicyclo[1.1.0]butanes","authors":"Peng-Fei Chen, Meng-Yuan Dong, Chun-Yu Han, Dong-Sheng Li, Yang Hong, Fei Xue, Fang Liu, Hong-Ping Deng","doi":"10.1021/acs.orglett.4c04702","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04702","url":null,"abstract":"Radical-initiated functionalization of bicyclo[1.1.0]butanes (BCBs) is a straightforward approach to accessing diverse cyclobutane derivatives. However, selective C(sp<sup>3</sup>)–H functionalization at the <i>C2</i> position of BCBs remains scarce. Herein, a mild protocol for the hydrogen-evolution of <i>C2</i> C(sp<sup>3</sup>)–H phosphorylation with BCBs enabled by photoinduced cobaloxime catalysis was realized in a regio- and diastereoselective manner. This oxidant- and additional photocatalyst-free method enabled C(sp<sup>3</sup>)–H phosphorylation with a wide range of BCBs and diarylphosphine oxides. The mechanism was studied via control experiments and DFT calculation. Moreover, the efficiency of this approach was highlighted in the synthesis of high-value, structurally complex molecules.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"24 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142981924","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Asymmetric Amplification in Oxypalladation/Malononitrile Addition Cascade Enabled by Heterochiral-Assembly of Products
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-15 DOI: 10.1021/acs.orglett.4c04591
Xiao-Wen Zhang, Qi-Yang Li, Wei Yan, Xu-Dong Hu, Wen-Bo Liu
{"title":"Asymmetric Amplification in Oxypalladation/Malononitrile Addition Cascade Enabled by Heterochiral-Assembly of Products","authors":"Xiao-Wen Zhang, Qi-Yang Li, Wei Yan, Xu-Dong Hu, Wen-Bo Liu","doi":"10.1021/acs.orglett.4c04591","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04591","url":null,"abstract":"An enantioselective oxypalladation/malononitrile addition cascade reaction of alkyne-tethered malononitriles was reported to synthesize enaminones bearing an all-carbon quaternary center. Using Pd(TFA)<sub>2</sub>/Pyox as a precatalyst, an array of enaminone products were obtained in moderate overall yields, with excellent er (93.5:6.5–99.5:0.5) in solution phase and nearly racemic in solid phase. The usage of 3,5-dinitrobenzoic acid as the nucleophile was proven to be crucial to this significant chiral amplification due to a heterochiral self-assembly of the products through an intermolecular multiple π–π stacking interaction. A strong positive nonlinear effect (NLE) was observed in solution phase, which was further highlighted by the access to an enantiopure enaminone (99.5:0.5 er) even using a partially enantiopure catalyst (54:46 er).","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"2 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142981923","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Late-Stage C–H Functionalization of Dehydroalanine-Containing Peptides with Arylthianthrenium Salts and Its Application in Synthesis of Tentoxin Analogue
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-14 DOI: 10.1021/acs.orglett.4c04535
Xing-Xing Ding, Bing-Tong Li, Lin Dong
{"title":"Late-Stage C–H Functionalization of Dehydroalanine-Containing Peptides with Arylthianthrenium Salts and Its Application in Synthesis of Tentoxin Analogue","authors":"Xing-Xing Ding, Bing-Tong Li, Lin Dong","doi":"10.1021/acs.orglett.4c04535","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04535","url":null,"abstract":"Dehydrophenylalanine has a characteristic unsaturated double bond that makes it indispensable in the context of peptides and proteins. In this study, we report the Pd-catalyzed C(sp<sup>2</sup>)–H arylation of dehydroalanine-containing peptides with arylthianthrenium salts under mild and base free conditions, which provides efficient access to dehydrophenylalanine-containing peptides. This approach enables the efficient coupling of different drug scaffolds and bioactive molecules to the peptides. Remarkably, the method could be used for the concise synthesis of tentoxin and its analogue.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"23 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142975668","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Combination of Tetrazole and 4-Azido-pyrazolotriazine Oxide: Balance of High Nitrogen, Energy, and Safety
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-14 DOI: 10.1021/acs.orglett.4c04507
Hanghong Fan, Jie Tang, Wei Hu, Xiaoxiao Zheng, Pengju Yang, Guangbin Cheng, Chuan Xiao, Hongwei Yang
{"title":"Combination of Tetrazole and 4-Azido-pyrazolotriazine Oxide: Balance of High Nitrogen, Energy, and Safety","authors":"Hanghong Fan, Jie Tang, Wei Hu, Xiaoxiao Zheng, Pengju Yang, Guangbin Cheng, Chuan Xiao, Hongwei Yang","doi":"10.1021/acs.orglett.4c04507","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04507","url":null,"abstract":"Energetic materials containing a pyrazolotriazine oxide skeleton have the potential for high performance. However, research on the pyrazolotriazine oxide skeleton is very limited due to the inherent ring system instability and limited synthetic approaches. In this paper, APTO and OPTO with a combination of high-nitrogen tetrazole and a promising azido-pyrazolotriazine oxide skeleton have been synthesized. Of these, OPTO and its energetic salts exhibit excellent detonation properties (<i>D</i><sub>v</sub> &gt; 8220 m s<sup>–1</sup>; <i>P</i> &gt; 26.50 GPa). Surprisingly, APTO exhibits a detonation performance (<i>D</i><sub>v</sub> = 8913 m s<sup>–1</sup>; <i>P</i> = 32.43 GPa) comparable to that of RDX.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"23 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142981925","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Serendipitous Discovery of Dearomatized Dimers in Anthracene Derivative Oxidation
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-14 DOI: 10.1021/acs.orglett.4c04417
Xinhao Fan, Huan Chen, Baotong Tian, Yuming Wen, Qiang Zhang
{"title":"Serendipitous Discovery of Dearomatized Dimers in Anthracene Derivative Oxidation","authors":"Xinhao Fan, Huan Chen, Baotong Tian, Yuming Wen, Qiang Zhang","doi":"10.1021/acs.orglett.4c04417","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04417","url":null,"abstract":"We present the serendipitous discovery of an unusual dimer formed from anthracene-derived polyarenes. Unlike the typical oxidative coupling of substituted aromatic scaffolds, the reaction yielded a dearomatized enone dimer as the sole product. This dearomatized motif, notably, does not undergo the commonly observed rearomatization, and no biaryl products were detected. The anthracene dimers were produced in excellent yields. Structural validation via single-crystal X-ray analysis revealed that the dimers feature an sp<sup>3</sup>–sp<sup>3</sup> carbon–carbon bond connecting two α,β-unsaturated enones, existing as a pair of diastereomers. These unique dimers underscore the critical role of serendipity in advancing organic synthesis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"52 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142975667","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Synthetic Strategy for Unsymmetrical α-Fluoro-α′-aryl Ketones
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-13 DOI: 10.1021/acs.orglett.4c04486
Shubham Dutta, Avijit Maity, Shengwen Yang, Rajendra K. Mallick, Manash P. Gogoi, Vincent Gandon, Akhila K. Sahoo
{"title":"Synthetic Strategy for Unsymmetrical α-Fluoro-α′-aryl Ketones","authors":"Shubham Dutta, Avijit Maity, Shengwen Yang, Rajendra K. Mallick, Manash P. Gogoi, Vincent Gandon, Akhila K. Sahoo","doi":"10.1021/acs.orglett.4c04486","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04486","url":null,"abstract":"α-Fluoro-α′-aryl ketones are crucial in pharmaceuticals and agrochemicals. However, synthesizing unsymmetrical α-fluoro-α′-aryl ketones poses regioselective challenges. This study presents a one-pot aryl-oxy-fluorination method for synthesizing such unsymmetrical fluoro-aryl ketones. Using ynamide, aryl boronic acid, and F-source under Pd-catalysis, this method efficiently produces a wide range of valuable α-fluoro-α′-aryl ketones with potential applications. Through a combination of control experiments and DFT studies, we proposed a reaction mechanism involving in situ acetic acid formation.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"11 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142968532","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 Cyclizative Carboxylation of Alkene-Tethered Aryl Isocyanides with Carbon Dioxide
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-13 DOI: 10.1021/acs.orglett.4c04426
Haitao Liu, Meng Guo, Mengying Jia, Jianwei Zhang, Xianxiu Xu
{"title":"Electrochemical Cyclizative Carboxylation of Alkene-Tethered Aryl Isocyanides with Carbon Dioxide","authors":"Haitao Liu, Meng Guo, Mengying Jia, Jianwei Zhang, Xianxiu Xu","doi":"10.1021/acs.orglett.4c04426","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04426","url":null,"abstract":"Herein, we present an unprecedented electrochemical reductive cyclizative carboxylation of <i>o</i>-vinylphenyl isocyanides with carbon dioxide achieved without the use of metal catalysts. This protocol demonstrates a broad substrate scope and good functional group tolerance, facilitating the rapid assembly of 2-oxoindolin-3-acetic acids in good to high yields with excellent regioselectivity. Furthermore, these structural motifs may have potential applications in formal synthesis of bioactive natural products.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"21 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142968407","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Reaction of Donor–Acceptor α-Diazo Esters and N,N-Dimethylformamide/γ-Lactams To Generate α-Amino-α-aroylethanoates
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-13 DOI: 10.1021/acs.orglett.4c03771
Xiaonan Mu, Yulong Niu, Minhui Guan, Hao Chen, Chuan-Ying Li, Lei Wang
{"title":"Reaction of Donor–Acceptor α-Diazo Esters and N,N-Dimethylformamide/γ-Lactams To Generate α-Amino-α-aroylethanoates","authors":"Xiaonan Mu, Yulong Niu, Minhui Guan, Hao Chen, Chuan-Ying Li, Lei Wang","doi":"10.1021/acs.orglett.4c03771","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03771","url":null,"abstract":"Herein, we present a metal-free, concise, and efficient protocol for the intermolecular reaction of amides (lactams) with donor–acceptor α-diazo esters to afford the functionalized α-amino-α-aroylethanoates. <i>N</i>-Methyl-2-pyrrolidone (NMP) and <i>N</i>,<i>N</i>-dimethylformamide (DMF) are employed as both reagents and solvents, allowing for the incorporation of all units into the products. The reaction is processed by the ester group migration and compatible with a broad range of substrates up to 50 examples.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"74 6 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142975669","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Rapid Assembly of 1,3-Dicarbonyl Fused 5-phenyl-1-Azabicyclo[3.1.0]hexanes and Their Cytotoxic Activities
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-13 DOI: 10.1021/acs.orglett.4c04394
Biral Kanti Pal, Kanchanbala Sahoo, Sourav Dey, Ruthrotha Selvi Bharathavikru, Barla Thirupathi
{"title":"Rapid Assembly of 1,3-Dicarbonyl Fused 5-phenyl-1-Azabicyclo[3.1.0]hexanes and Their Cytotoxic Activities","authors":"Biral Kanti Pal, Kanchanbala Sahoo, Sourav Dey, Ruthrotha Selvi Bharathavikru, Barla Thirupathi","doi":"10.1021/acs.orglett.4c04394","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04394","url":null,"abstract":"Synthesis of complex, multiring, spirocyclic, 1,3-dicarbonyl fused, and highly functionalized 5-phenyl-1-azabicyclo[3.1.0]hexanes (ABCH) has been achieved by an intermolecular reaction of 2-(2′-ketoalkyl)-1,3-indandiones or α,γ-diketo esters with (1-azidovinyl)benzenes under transition metal-free conditions. The reaction proceeds in a highly diastereoselective manner with a wide range of functional groups and provides moderate to good yields. Additionally, we have studied the preliminary biological activities of a few synthetic compounds against HeLa and triple-negative breast cancer (TNBC) cell lines.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"43 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142975670","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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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