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Ni-Catalyzed Electro-Reductive Cross-Electrophile Couplings of Alkyl Amine-Derived Radical Precursors with Aryl Iodides. 镍催化烷基胺衍生自由基前体与芳基碘化物的电诱导交叉亲电偶联。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2023-05-23 DOI: 10.1021/acs.joc.3c00859
Lars J Wesenberg, Alessandra Sivo, Gianvito Vilé, Timothy Noël
{"title":"Ni-Catalyzed Electro-Reductive Cross-Electrophile Couplings of Alkyl Amine-Derived Radical Precursors with Aryl Iodides.","authors":"Lars J Wesenberg, Alessandra Sivo, Gianvito Vilé, Timothy Noël","doi":"10.1021/acs.joc.3c00859","DOIUrl":"10.1021/acs.joc.3c00859","url":null,"abstract":"<p><p>In recent years, the \"Escape-from-Flatland\" trend has prompted the synthetic community to develop a set of cross-coupling strategies to introduce sp<sup>3</sup>-carbon-based fragments in organic compounds. This study presents a novel nickel-catalyzed electrochemical methodology for reductive cross-electrophile coupling. The method enables C(sp<sup>2</sup>)-C(sp<sup>3</sup>) linkages using inexpensive amine-derived radical precursors and aryl iodides. The use of electrochemistry as a power source reduces waste and avoids chemical reductants, making this approach a more sustainable alternative to traditional cross-coupling methods.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16121-16125"},"PeriodicalIF":3.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11574849/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9512274","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Light-Induced Difunctionalization of Alkenes with Polyhaloalkanes and Quinoxalin-2(1H)-ones. 光诱导烯与多卤烷和喹喔啉-2(1H)-酮的双官能化。
IF 4.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-11-01 DOI: 10.1021/acs.joc.4c02119
Vivek Kumar, Akash Bisoyi, Fathima Beevi V, Veera Reddy Yatham
{"title":"Light-Induced Difunctionalization of Alkenes with Polyhaloalkanes and Quinoxalin-2(1<i>H</i>)-ones.","authors":"Vivek Kumar, Akash Bisoyi, Fathima Beevi V, Veera Reddy Yatham","doi":"10.1021/acs.joc.4c02119","DOIUrl":"10.1021/acs.joc.4c02119","url":null,"abstract":"<p><p>Herein, we report a metal-free light-induced three-component reaction for the synthesis of polychloroalkyl-substituted quinoxalin-2(1<i>H</i>)-ones using commercially available alkenes, polyhalo alkanes, and quinoxalin-2(1<i>H</i>)-ones. Preliminary mechanistic studies suggested the generation of radical intermediates via an EDA-complex, single electron transfer, or halogen atom transfer pathway. Under mild reaction conditions, various alkenes and quinoxalin-2(1<i>H</i>)-ones containing different functional groups are compatible, providing the corresponding polychloroalkyl-substituted quinoxalin-2(1<i>H</i>)-ones in moderate to good yields.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16964-16968"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142556657","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
Enantioselective Synthesis of Azatricycles via Post-Ugi Cyclizations. 通过乌基后环化技术对氮杂环进行对映选择性合成。
IF 4.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-11-04 DOI: 10.1021/acs.joc.4c01970
Mandweep Bhumij, Mayur D Ambule, Sagar Sinha, Surbhi Prabhat, Ruchir Kant, Ajay Kumar Srivastava
{"title":"Enantioselective Synthesis of Azatricycles via Post-Ugi Cyclizations.","authors":"Mandweep Bhumij, Mayur D Ambule, Sagar Sinha, Surbhi Prabhat, Ruchir Kant, Ajay Kumar Srivastava","doi":"10.1021/acs.joc.4c01970","DOIUrl":"10.1021/acs.joc.4c01970","url":null,"abstract":"<p><p>We report a new method to create enantioenriched azatricycles using chiral α-amino acids in a two-step process after an Ugi reaction. Amino acids are great building blocks for making pure chiral molecules. Using chiral natural molecules in multicomponent reactions (MCRs) helps increase their variety by adding new chiral centers. The Ugi reaction, discovered by Ivar Karl Ugi in 1959, is a versatile MCR that helps create complex molecular structures and natural products through additional transformations called post-Ugi modifications. Designing these modifications requires selecting the right amine, acid, aldehyde/ketone, and isocyanide. Amino acids, with their primary amine and carboxylic acid groups and a pre-existing chiral center, are ideal for making diverse and selective post-Ugi modifications. Our method uses <i>ipso</i>-cyclization and aza-Michael cyclization with hypervalent iodine to create various azaspirotricyclic structures with high stereocontrol. This approach works well with different substrates and shows promise for further development in drug discovery.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16679-16696"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142575436","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
Highly Regioselective Dehydrogenative Hydrazination of Tropones. 托品的高区域选择性脱氢肼化作用。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 DOI: 10.1021/acs.joc.4c02358
Yan Wang, Muliang Zhang, Shi-Kai Tian
{"title":"Highly Regioselective Dehydrogenative Hydrazination of Tropones.","authors":"Yan Wang, Muliang Zhang, Shi-Kai Tian","doi":"10.1021/acs.joc.4c02358","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02358","url":null,"abstract":"<p><p>Direct C(sp<sup>2</sup>)-H bond functionalization of the tropone skeleton constitutes an atom-economical strategy to access substituted tropones that exist in some bioactive compounds. Herein, we report a convenient method for the preparation of 2-hydrazinotropones via C(sp<sup>2</sup>)-H bond functionalization. A variety of tropones participated in the dehydrogenative hydrazination reaction with hydrazine, delivering structurally diverse 2-hydrazinotropones in moderate to good yields with extremely high regioselectivity. This method is featured by operational simplicity and metal-free reaction conditions, thereby tolerating various functional groups.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142637917","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
Expedited Aminoglutarimide C–N Cross-Coupling Enabled by High-Throughput Experimentation 通过高通量实验实现快速氨基戊二酰亚胺 C-N 交叉偶联
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 DOI: 10.1021/acs.joc.4c02536
Jacqueline W. Gu, Martins S. Oderinde, Hui Li, Frederick Roberts, Jacob M. Ganley, Maximilian D. Palkowitz
{"title":"Expedited Aminoglutarimide C–N Cross-Coupling Enabled by High-Throughput Experimentation","authors":"Jacqueline W. Gu, Martins S. Oderinde, Hui Li, Frederick Roberts, Jacob M. Ganley, Maximilian D. Palkowitz","doi":"10.1021/acs.joc.4c02536","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02536","url":null,"abstract":"A simple protocol for the Buchwald–Hartwig cross-coupling of (hetero)aryl halides with unprotected aminoglutarimide to afford diverse cereblon binding motifs is disclosed. The development of this C–N cross-coupling method was enabled by high-throughput combinatory screening of solvents, bases, temperatures, and ligands. Scope studies revealed generality across various heteroaryl and aryl halides with the reaction proceeding under mild conditions. In comparison, this method demonstrated strategic superiority over previously reported approaches, as evidenced by a significant decrease in step count from known syntheses in the patent literature.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"246 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142637773","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
Intramolecular/Intermolecular Sequential Cyclization Accompanied by Double C-F Bond Cleavage: Access to Tricyclic Fluorine-Containing Pyrano[3,2-c]chromenes. 伴随双 C-F 键裂解的分子内/分子间顺序环化：获得三环含氟吡喃并[3,2-c]色烯。
IF 4.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-10-28 DOI: 10.1021/acs.joc.4c01854
Dong-Sheng Yang, Xiang-Long Chen, Chun-Yan Wu, You Zhou, Li-Sheng Wang, Yan-Dong Wu, An-Xin Wu
{"title":"Intramolecular/Intermolecular Sequential Cyclization Accompanied by Double C-F Bond Cleavage: Access to Tricyclic Fluorine-Containing Pyrano[3,2-<i>c</i>]chromenes.","authors":"Dong-Sheng Yang, Xiang-Long Chen, Chun-Yan Wu, You Zhou, Li-Sheng Wang, Yan-Dong Wu, An-Xin Wu","doi":"10.1021/acs.joc.4c01854","DOIUrl":"10.1021/acs.joc.4c01854","url":null,"abstract":"<p><p>Defluorinative cyclization of CF<sub>3</sub>-alkenes has emerged as a reliable strategy for crafting intricate polycyclic frameworks. In this study, a facile defluorinative bicyclization approach was developed for the construction of 4<i>H</i>,5<i>H</i>-pyrano[3,2-<i>c</i>]chromenes under mild conditions involving a sequence of intramolecular cyclization and intermolecular defluoroheterocyclization. A variety of polysubstituted 4<i>H</i>,5<i>H</i>-pyrano[3,2-<i>c</i>]chromenes featuring C2-fluorine could be synthesized in good yields with excellent tolerance toward various functional groups. Moreover, the introduction of a C-F bond provides additional possibilities for further modification of this skeleton. The product features aggregation-induced emission (AIE) characteristics after simple modification, which is promising for chemical and biomedical imaging.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16553-16563"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142491174","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
Simple Parameters and Data Processing for Better Signal-to-Noise and Temporal Resolution in In Situ 1D NMR Reaction Monitoring. 简化参数和数据处理，提高原位一维核磁共振反应监测的信噪比和时间分辨率
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-10-31 DOI: 10.1021/acs.joc.4c01882
Annabel Flook, Guy C Lloyd-Jones
{"title":"Simple Parameters and Data Processing for Better Signal-to-Noise and Temporal Resolution in <i>In Situ</i> 1D NMR Reaction Monitoring.","authors":"Annabel Flook, Guy C Lloyd-Jones","doi":"10.1021/acs.joc.4c01882","DOIUrl":"10.1021/acs.joc.4c01882","url":null,"abstract":"<p><p><i>In situ</i> 1D NMR spectroscopic reaction monitoring allows detailed investigation of chemical kinetics and mechanism. Concentration versus time data are derived from a time series of NMR spectra. Each spectrum in the series is obtained by Fourier transform of the corresponding FID. When the spectrometer outputs FIDs recorded from multiple scans, the spectra benefit from an increase in signal-to-noise (S/N). However, this reduces the number of FIDs and, thus, kinetic data points. We report a simple alternative in which the same number of scans is acquired by the spectrometer, but each scan is saved independently. Signal averaging is then conducted by postacquisition processing. This leads to an increase in both the S/N and the number of kinetic data points and can avoid \"overaveraging\" effects. The entire series of single-scan FIDs spanning the reaction lifetime can be summed to yield a \"total reaction spectrum\" in which intermediates can be identified. The method can be applied in coherence with phase cycling to minimize spectral distortion during solvent signal suppression. Overall, the approach simplifies the preacquisition parameters to the estimation of the reaction duration and <i>T</i><sub>1</sub><sup>max</sup> and then the selection of the pulse angle, θ, and scan repetition time, τ<sub>R</sub>, without the need to set the signal averaging before the experiment.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16586-16593"},"PeriodicalIF":3.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11574850/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142556661","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Asymmetric Vinylogous Michael/Oxa-Michael Tandem Reaction between β,γ-Unsaturated Amides and Isatin-Derived β,γ-Unsaturated α-Ketoesters β,γ-不饱和酰胺与异铂衍生的 β,γ-不饱和 α-酮酯之间的不对称乙烯基迈克尔/六迈克尔串联反应
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 DOI: 10.1021/acs.joc.4c02066
Shan-Shan Xu, Zi-Yu Li, Meng-Yu Liu, Feng Sha, Xin-Yan Wu
{"title":"Asymmetric Vinylogous Michael/Oxa-Michael Tandem Reaction between β,γ-Unsaturated Amides and Isatin-Derived β,γ-Unsaturated α-Ketoesters","authors":"Shan-Shan Xu, Zi-Yu Li, Meng-Yu Liu, Feng Sha, Xin-Yan Wu","doi":"10.1021/acs.joc.4c02066","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02066","url":null,"abstract":"An organocatalytic asymmetric vinylogous Michael/oxa-Michael tandem reaction between β,γ-unsaturated pyrazoleamides and isatin-derived β,γ-unsaturated ketoesters has been developed with excellent regio-, diastereo-, and enantioselectivities. The methodology provides an effective approach to construct enantiomerically pure 3,4′-pyranyl spirooxindole derivatives containing three contiguous chiral centers. Moreover, the transformations of the chiral products, including the removal and reduction of the pyrazole group, have been investigated.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"21 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142637774","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
Access to Ketones via Nickel-Catalyzed Coupling between S-2-Pyridyl Thioesters and Redox-Active Esters Using an Organic Reductant 使用有机还原剂，通过镍催化 S-2-吡啶硫酯与氧化还原活性酯之间的偶联获得酮体
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 DOI: 10.1021/acs.joc.4c01242
Jiang-Hong Liu, Ze-Yu Tian, Zhen-Ye Wu, Tian-Le Huang, Zheng Lin, Le Zhang, Jian Chen, Li Hai, Li Guo, Yong Wu
{"title":"Access to Ketones via Nickel-Catalyzed Coupling between S-2-Pyridyl Thioesters and Redox-Active Esters Using an Organic Reductant","authors":"Jiang-Hong Liu, Ze-Yu Tian, Zhen-Ye Wu, Tian-Le Huang, Zheng Lin, Le Zhang, Jian Chen, Li Hai, Li Guo, Yong Wu","doi":"10.1021/acs.joc.4c01242","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01242","url":null,"abstract":"A nickel-catalyzed coupling between S-2-pyridyl thioesters and redox-active esters has been reported. Diludine was used as a reductant in this strategy. Our method rapidly achieves the target ketone products in moderate to good yield. The construction of nonanomeric C-acyl glycosides was realized through the approach as well.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"16 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142637851","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
Pd-IHept-Catalyzed Ring-Opening of gem-Difluorocyclopropanes with Malonates Via Selective C-C Bond Cleavage: Synthesis of Monofluoroalkenes. Pd-IHept催化丙二酸二氟环丙烷选择性C-C键断裂开环：一氟烯烃的合成。
IF 4.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2023-09-22 DOI: 10.1021/acs.joc.3c00744
Yuxuan Yan, Huijun Qian, Leiyang Lv, Zhiping Li
{"title":"Pd-IHept-Catalyzed Ring-Opening of <i>gem</i>-Difluorocyclopropanes with Malonates Via Selective C-C Bond Cleavage: Synthesis of Monofluoroalkenes.","authors":"Yuxuan Yan, Huijun Qian, Leiyang Lv, Zhiping Li","doi":"10.1021/acs.joc.3c00744","DOIUrl":"10.1021/acs.joc.3c00744","url":null,"abstract":"<p><p>Monofluoroalkene scaffolds are frequently found in various functional molecules. Herein, we report a Pd-IHept-catalyzed (NHC = N-heterocyclic carbene) defluorinative functionalization approach for the synthesis of monofluoroalkenes from <i>gem</i>-difluorocyclopropanes and malonates. The flexible yet sterically hindered <i>N</i>,<i>N</i>'-bis(2,6-di(4-heptyl)phenyl)imidazol-2-ylidene ligand plays a key role in ensuring the high reaction efficiency. In addition, sterically hindered 1,1- and 1,2-disubstituted <i>gem</i>-difluorocyclopropanes could also be used in this transformation.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16253-16261"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41089613","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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