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CuF2/DTBP-Catalyzed Chan-Lam Coupling of Oxazolidinones with Arylboronic Acid Pinacol Ester: Scope and Application
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-25 DOI: 10.1021/acs.joc.5c00283
Tanumay Roy, Krishanu Mondal, Pallabi Halder, Arunava Sengupta, Parthasarathi Das
{"title":"CuF2/DTBP-Catalyzed Chan-Lam Coupling of Oxazolidinones with Arylboronic Acid Pinacol Ester: Scope and Application","authors":"Tanumay Roy, Krishanu Mondal, Pallabi Halder, Arunava Sengupta, Parthasarathi Das","doi":"10.1021/acs.joc.5c00283","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00283","url":null,"abstract":"A new combination of CuF<sub>2</sub>/DTBP-catalyzed <i>N</i>-arylation of oxazolidinones, amides, amines, and azoles has been explored with arylboronic acid pinacol esters (arylBpin). This methodology has also been applied to the synthesis of oxazolidinone-based marketed drugs, including Rivaroxaban, Linezolid, Sutezolid, and Toloxatone. Mechanistic investigations using various spectroscopic techniques and DFT studies revealed the role of DTBP/MeOH in the catalytic process.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"70 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143876273","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
Reductive Breakage of the S–N Bond in S-Amidino Sulfenamides
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-25 DOI: 10.1021/acs.joc.4c02898
Qi Hou, Zhijun Yuan, Yaoping Ruan, Bohong Lin, Jianming Liang, Jing Zhang
{"title":"Reductive Breakage of the S–N Bond in S-Amidino Sulfenamides","authors":"Qi Hou, Zhijun Yuan, Yaoping Ruan, Bohong Lin, Jianming Liang, Jing Zhang","doi":"10.1021/acs.joc.4c02898","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02898","url":null,"abstract":"In this study, reductive breakage of the S–N bond on <i>S</i>-amidino sulfenamides was examined to explore prodrug or covalent drug chemistry for thiourea compounds. Upon thiol treatment, efficient release of varying thioureas could be reached, with Pd catalysis further accelerating this process. Preliminary application to antithyroid drug methylthiouracil confirmed cysteine-triggered release of the parent drug, although further development was hampered by stability issues. These findings highlight the potential of tunable sulfenamide prodrugs to balance release kinetics and stability for thiourea therapeutics.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"14 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143876177","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 Alkylation of Malononitrile-Assisted Ketones through Deaminative Couplings
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-25 DOI: 10.1021/acs.joc.5c00297
Vadla Shiva Prasad, Silari Mohana Krishna, Vadithya Ranga Rao, Dharavath Ravi, Chelukalapally Anil Kumar, Praveen Reddy Adiyala
{"title":"Visible Light-Induced Alkylation of Malononitrile-Assisted Ketones through Deaminative Couplings","authors":"Vadla Shiva Prasad, Silari Mohana Krishna, Vadithya Ranga Rao, Dharavath Ravi, Chelukalapally Anil Kumar, Praveen Reddy Adiyala","doi":"10.1021/acs.joc.5c00297","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00297","url":null,"abstract":"The direct alkylation of carbonyl compounds at α &amp; β positions represents a significant challenge. Here, we report a catalyst-free visible light-induced deaminative alkylation that efficiently produces α, β-alkylated malononitrile-assisted ketones. Mechanistic studies suggested an EDA complex is formed by the Katritzky salt and the α &amp; β carbanion of malononitrile-aided ketones, which permits the disruption of C–N bonds and the generation of alkyl radicals. Remarkably, this strategy eliminates the need for metal catalysts, additives, and ligands offering enhanced environmental sustainability and features mild, catalyst-free, and broad functional group tolerance. Our optimized catalyst-free condition under blue LED light yielded regio isomers of malononitrile-assisted ketones in good to excellent yields with diverse electronic properties and substitutions. Implementation of the flow setup to this batch protocol enhanced the efficiency of the reaction, demonstrating robustness and sustainability in organic synthesis.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"5 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143876178","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
Regioselective, Lewis Acid-Catalyzed Ring-Openings of 2,3-Aziridyl Alcohols with Azoles
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-25 DOI: 10.1021/acs.joc.5c00380
Benjamin Zheng, Mark S. Taylor
{"title":"Regioselective, Lewis Acid-Catalyzed Ring-Openings of 2,3-Aziridyl Alcohols with Azoles","authors":"Benjamin Zheng, Mark S. Taylor","doi":"10.1021/acs.joc.5c00380","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00380","url":null,"abstract":"Methods for regioselective ring-opening reactions of <i>N</i>-sulfonyl-protected aziridyl alcohols with azole nucleophiles have been developed. Several classes of azoles, including indazole, substituted pyrazole, benzotriazole, and tetrazole, have been employed as reaction partners, giving rise to C3-selective opening and &gt;3:1 <i>N</i>-selectivity. BF<sub>3</sub>•OEt<sub>2</sub> is the optimal catalyst for most substrate combinations, although examples where diphenylborinic acid (Ph<sub>2</sub>BOH) provides higher yields, or where the reactions proceed efficiently without a catalyst, are also described. Computational modeling of the BF<sub>3</sub>•OEt<sub>2</sub>-catalyzed reaction is consistent with the observed regiochemical outcome. The calculated ring-opening transition state appears to be stabilized by an unconventional OH···FB hydrogen-bonding interaction.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"53 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143876179","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
Asymmetric Synthesis of Tetrahydrofurans with Vicinal Stereocenters by RhII/RuII Relay Catalysis
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-25 DOI: 10.1021/acs.joc.5c00324
Xuejiao Li, Fang-Jie Liu, Baihua Ye
{"title":"Asymmetric Synthesis of Tetrahydrofurans with Vicinal Stereocenters by RhII/RuII Relay Catalysis","authors":"Xuejiao Li, Fang-Jie Liu, Baihua Ye","doi":"10.1021/acs.joc.5c00324","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00324","url":null,"abstract":"CpRu-catalyzed asymmetric allylic alkylation serves as a versatile synthetic tool but remains underexplored. Herein, we report a relay system combining achiral Rh<sub>2</sub>(OAc)<sub>4</sub> and a chiral pyridine-oxazoline-ligated Cp*Ru catalyst for asymmetric coupling of cinnamyl chlorides with diazo esters, generating silyl enol ethers <i>in situ</i> as key nucleophilic intermediates. This strategy affords chiral tetrahydrofuran derivatives with two vicinal stereocenters. Catalyst compatibility, excellent regioselectivity, and good enantioselectivity highlight its potential. Computational studies reveal the crucial role of Ru-centered chirality in reaction control.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"69 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872846","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
Total Synthesis of the Melodinus Alkaloid (±)-Melohemsine K
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-25 DOI: 10.1021/acs.joc.5c00545
Shanhao Lin, Hao Jing, Jinbo Duan, Jing Fang, Gaoyuan Zhao, Xingang Xie, Huilin Li, Xuegong She
{"title":"Total Synthesis of the Melodinus Alkaloid (±)-Melohemsine K","authors":"Shanhao Lin, Hao Jing, Jinbo Duan, Jing Fang, Gaoyuan Zhao, Xingang Xie, Huilin Li, Xuegong She","doi":"10.1021/acs.joc.5c00545","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00545","url":null,"abstract":"The first total synthesis of the novel <i>Melodinus</i> alkaloid melohemsine K is described in five steps from known precursors. The key reaction of the synthesis is a tandem enamine formation/retro-aza-Michael reaction/Diels–Alder cycloaddition/intramolecular lactamization reaction cascade between indole-fused azepine and aldehyde precursors, forging the critical CDE tricyclic system. The synthesis provided a general approach to novel <i>Melodinus</i> alkaloids.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"12 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872918","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 Reductive Hydroamination of Alkenes and 1,3-Dienes with Nitroarenes
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-24 DOI: 10.1021/acs.joc.4c02150
Zi-Heng Zhang, Shuang-Shuang Ma, Yuan-Yuan Jiang, Jin-Qing Lin, Bao-Hua Xu
{"title":"Copper-Catalyzed Reductive Hydroamination of Alkenes and 1,3-Dienes with Nitroarenes","authors":"Zi-Heng Zhang, Shuang-Shuang Ma, Yuan-Yuan Jiang, Jin-Qing Lin, Bao-Hua Xu","doi":"10.1021/acs.joc.4c02150","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02150","url":null,"abstract":"In this study, copper-catalyzed reductive hydroamination of alkenes and 1,3-dienes with nitroarenes was developed. Such umpolung hydroamination of unsaturated C═C double bonds exhibited Markovnikov selectivity, and the hydroamination of 1,3-dienes preferred 1,2-addition. Mechanistic studies suggested the system proceeds through a radical pathway with the concomitant activation of both substrates to nucleophilic alkyl radical species and electrophilic nitro-based intermediates, respectively. The attack of alkyl radical species on the N atom of nitro-based intermediates yielded the desired amines. However, this C–N cross-coupling strongly competed with the self-reduction of each species under such a system.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"8 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143867137","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 and 1,3-Sulfonyl Migration Enabled Installation of Azaindoles in the Periphery of Aryl Rings: Synthesis of Sulfonylated Pyrrolo[2,3-b]quinolines and Investigation of Antimalarial Potency
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-24 DOI: 10.1021/acs.joc.5c00170
Shivani Choudhary, Gayyur, Siddhant, Ashan Manhas, Ruchir Kant, Nayan Ghosh
{"title":"Copper-Catalyzed and 1,3-Sulfonyl Migration Enabled Installation of Azaindoles in the Periphery of Aryl Rings: Synthesis of Sulfonylated Pyrrolo[2,3-b]quinolines and Investigation of Antimalarial Potency","authors":"Shivani Choudhary, Gayyur, Siddhant, Ashan Manhas, Ruchir Kant, Nayan Ghosh","doi":"10.1021/acs.joc.5c00170","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00170","url":null,"abstract":"Herein, an atom efficient and one-pot protocol, offering a series of sulfonylated pyrrolo[2,3-<i>b</i>]quinolines via C–N, C–C, and C–S bond formation, has been developed with an inexpensive copper catalyst. Notably, the reaction proceeds via a double-annulation reaction followed by a 1,3-sulfonyl migration sequence. Moreover, the method is applicable to a broad range of 2-carbonylanilines. Furthermore, synthetic applications and the scale-up reaction highlight the utility potential of this protocol. In addition, the antimalarial property of sulfonylated pyrrolo[2,3-<i>b</i>]quinolines showed parasite inhibition without cytotoxic effects in mammalian cells.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"75 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872920","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
Mechanosynthesis of β-Naphthol Derivatives via Triflic Anhydride-Mediated Reaction of Arylacetic Acids with Arylalkynes
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-24 DOI: 10.1021/acs.joc.5c00204
Xu-Ling Xia, Liang Li, Jun-Shen Chen, Li-Feng Guo, Guan-Wu Wang
{"title":"Mechanosynthesis of β-Naphthol Derivatives via Triflic Anhydride-Mediated Reaction of Arylacetic Acids with Arylalkynes","authors":"Xu-Ling Xia, Liang Li, Jun-Shen Chen, Li-Feng Guo, Guan-Wu Wang","doi":"10.1021/acs.joc.5c00204","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00204","url":null,"abstract":"The mechanosynthesis of β-naphthol derivatives was accomplished through triflic anhydride-mediated cyclization reactions of arylacetic acids with arylalkynes in moderate to good yields by ball milling at room temperature. The present protocol featured solvent-free and simple conditions, a short reaction time, and easily available and inexpensive reagents.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"7 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143867058","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
Halogen Bonding Promoted Photoinduced Synthesis of 3,3-Disubstituted Oxindoles
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-24 DOI: 10.1021/acs.joc.4c02963
Kun-Quan Chen, Jia Zhang, Xiao-Bo Chen, De-Qun Sun
{"title":"Halogen Bonding Promoted Photoinduced Synthesis of 3,3-Disubstituted Oxindoles","authors":"Kun-Quan Chen, Jia Zhang, Xiao-Bo Chen, De-Qun Sun","doi":"10.1021/acs.joc.4c02963","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02963","url":null,"abstract":"A photoinduced and catalyst-free radical cyclization process for the synthesis of 3,3-disubstituted oxindoles is reported. This method utilizes readily available α-bromoanilides as substrates, showcasing a broad substrate scope. The reaction mechanism is facilitated by a photoactivated charge transfer complex based on the halogen bonding of α-bromoanilide with TMG and alcohol.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"69 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143872919","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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