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AgSbF6 Catalyzed Reduction of Nitroarenes by Phenylsilane to Anilines
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-21 DOI: 10.1021/acs.joc.4c02639
Priyabrata Biswal, Gobbilla Sai Kumar, Vadapalli Chandrasekhar
{"title":"AgSbF6 Catalyzed Reduction of Nitroarenes by Phenylsilane to Anilines","authors":"Priyabrata Biswal, Gobbilla Sai Kumar, Vadapalli Chandrasekhar","doi":"10.1021/acs.joc.4c02639","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02639","url":null,"abstract":"AgSbF<sub>6</sub>-catalyzed activation of phenylsilane (PhSiH<sub>3</sub>) enables the efficient reduction of nitroarenes to produce the corresponding anilines. This methodology operates under additive-free conditions, making it highly efficient, scalable, and compatible with a wide range of electronically diverse nitroarenes. The utility of this method is exemplified by employing a cheap, commercially available metal catalyst for the facile synthesis of various anilines. Furthermore, the methodology has been extended to the synthesis of intermediates for drug molecules, demonstrating its broad applicability.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"20 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462972","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 Site-Selective C–H Sulfonylation via Aryl Thianthrenium Salts to Access Diarylsulfones
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-21 DOI: 10.1021/acs.joc.4c02913
Chunjie Ni, Jin-Ping Liu, Xiao-Xu Zhang, Zi-Yi Wang, Zhanhang Liang, Chen Chen, Di Qiu
{"title":"Palladium-Catalyzed Site-Selective C–H Sulfonylation via Aryl Thianthrenium Salts to Access Diarylsulfones","authors":"Chunjie Ni, Jin-Ping Liu, Xiao-Xu Zhang, Zi-Yi Wang, Zhanhang Liang, Chen Chen, Di Qiu","doi":"10.1021/acs.joc.4c02913","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02913","url":null,"abstract":"We presented a highly efficient palladium-catalyzed site-selective C–H sulfonylation reaction via aryl thianthrenium salts. By utilizing readily available and cost-effective arenes along with sodium sulfinates, we achieved the C(sp<sup>2</sup>)–S cross-coupling with high efficiency, establishing a dependable method for synthesizing diarylsulfones with satisfactory yields. This method exhibits excellent tolerance toward functional groups, scalability, and the synthesis or late-stage functionalization of bioactive molecules, making it a valuable sulfonylation tool for drug modifications.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462971","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 Unprotected Tryptophan Derivatives Using Gramines via Ni(II) Complexes
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-21 DOI: 10.1021/acs.joc.4c02406
Zhekai Xiao, Yazhou Li, Yuzhu Wu, Qiangqiang Chen, Shengbin Zhou, Vadim A. Soloshonok, Jiang Wang, Hong Liu
{"title":"Asymmetric Synthesis of Unprotected Tryptophan Derivatives Using Gramines via Ni(II) Complexes","authors":"Zhekai Xiao, Yazhou Li, Yuzhu Wu, Qiangqiang Chen, Shengbin Zhou, Vadim A. Soloshonok, Jiang Wang, Hong Liu","doi":"10.1021/acs.joc.4c02406","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02406","url":null,"abstract":"We herein report the synthesis of substituted tryptophans using Ni(II) complexes of glycine and gramines. This reaction proceeds under operationally convenient and mild conditions, using inexpensive, nontoxic, and easily accessible reagents. The reactions feature high yields and virtually complete thermodynamically controlled diastereoselectivity, providing a convenient method for the synthesis of tailor-made tryptophans.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"96 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462963","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 N-Aryl and N-Alkyl Phthalimides via Denitrogenative Cyanation of 1,2,3-Benzotriazin-4(3H)-ones
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-21 DOI: 10.1021/acs.joc.4c02823
Ramaraju Korivi, Jagannath Rana, Baburaj Baskar, Subramaniyan Mannathan
{"title":"Synthesis of N-Aryl and N-Alkyl Phthalimides via Denitrogenative Cyanation of 1,2,3-Benzotriazin-4(3H)-ones","authors":"Ramaraju Korivi, Jagannath Rana, Baburaj Baskar, Subramaniyan Mannathan","doi":"10.1021/acs.joc.4c02823","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02823","url":null,"abstract":"An efficient metal-free approach for synthesizing <i>N</i>-aryl- and <i>N</i>-alkyl phthalimide derivatives from 1,2,3-benzotriazin-4(3<i>H</i>)-ones is described. The reaction likely proceeds via a denitrogenative cyanation pathway, utilizing TMSCN as the cyanide source. This method is straightforward as well as scalable and supports a wide range of substrates with high functional group tolerance, yielding diverse phthalimide derivatives in good to excellent yields. The utility of this method is further highlighted by the successful synthesis of a tyrosinase inhibitor analogue in good yield.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462965","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 a Natural Product-Based 5H-Thiazolo[5',4':5,6]pyrido[2,3-b]indole Derivative via Solid-Phase Synthesis.
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1021/acs.joc.4c03094
Jimin Moon, Shinae Kim, Shuanghui Hua, Hyojin Lee, Jungtae Kim, Taeho Lee
{"title":"Synthesis of a Natural Product-Based 5<i>H</i>-Thiazolo[5',4':5,6]pyrido[2,3-<i>b</i>]indole Derivative via Solid-Phase Synthesis.","authors":"Jimin Moon, Shinae Kim, Shuanghui Hua, Hyojin Lee, Jungtae Kim, Taeho Lee","doi":"10.1021/acs.joc.4c03094","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03094","url":null,"abstract":"<p><p>The solid-phase synthesis method is optimized for building chemical libraries. Furthermore, chemical libraries are essential tools in drug discovery used to identify hit compounds. We constructed a 5<i>H</i>-thiazolo[5',4':5,6]pyrido[2,3-<i>b</i>]indole derivative library using solid-phase synthesis. The indole insertion reaction at the benzylic position using a Lewis acid and the oxidative cyclization reaction using iodine were used for synthesis. Using optimized solution-phase reaction conditions, a solid-phase synthesis method comprising a total of eight steps was employed to build a 5<i>H</i>-thiazolo[5',4':5,6]pyrido[2,3-<i>b</i>]indole derivative library. In addition, we found an efficient compound library synthesis route with each synthetic step having a yield of 62-82%.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143456290","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
Halogenase-Assisted Biocatalytic Derivatization of Aminothiazoles and Cephalosporin Antibiotics
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1021/acs.joc.4c03043
Paul J. Branham, Nirmal Saha, Sophia E. Oyelere, Vinayak Agarwal
{"title":"Halogenase-Assisted Biocatalytic Derivatization of Aminothiazoles and Cephalosporin Antibiotics","authors":"Paul J. Branham, Nirmal Saha, Sophia E. Oyelere, Vinayak Agarwal","doi":"10.1021/acs.joc.4c03043","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03043","url":null,"abstract":"With a view toward the prominence of brominated intermediates in chemical synthesis, we describe here a biocatalytic scheme for the enzymatic bromination of 2-aminothiazoles using a marine macroalgal brominase in reaction conditions that are directly compatible with Suzuki–Miyaura cross-coupling reactions. Enzymatically delivered brominated thiazoles, without intermediary purification, are arylated in high yields. We demonstrate the applicability of the methodology described herein in derivatizing clinically administered cephalosporin antibiotics and prodrugs in an aqueous solvent and mild reaction conditions.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143463015","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
Stereoselective Synthesis of (R)-all-trans-13,14-Dihydroretinol and -Retinoic Acid
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1021/acs.joc.4c03173
Paul Wienecke, Adriaan J. Minnaard
{"title":"Stereoselective Synthesis of (R)-all-trans-13,14-Dihydroretinol and -Retinoic Acid","authors":"Paul Wienecke, Adriaan J. Minnaard","doi":"10.1021/acs.joc.4c03173","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03173","url":null,"abstract":"Vitamin A (or all-<i>trans</i>-retinol) metabolites are involved in a wide range of cellular processes. However, the investigation of their biological role is hampered due to their very limited availability. Herein we report a stereoselective total synthesis of the vitamin A metabolites (<i>R</i>)-all-<i>trans</i>-13,14-dihydroretinol and -retinoic acid, applying an <i>E</i>-selective HWE olefination and a Ru(II) catalyzed intramolecular 7-<i>endo</i>-<i>dig</i> hydrosilylation as the key steps.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"50 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143463017","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
Bi(III)-Catalyzed Newman–Kwart Rearrangement for Synthesizing S-Heteroaryl Thiocarbamates
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1021/acs.joc.4c02728
Yuma Okuda, Keita Yamazaki, Tetsuhiro Nemoto
{"title":"Bi(III)-Catalyzed Newman–Kwart Rearrangement for Synthesizing S-Heteroaryl Thiocarbamates","authors":"Yuma Okuda, Keita Yamazaki, Tetsuhiro Nemoto","doi":"10.1021/acs.joc.4c02728","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02728","url":null,"abstract":"Newman–Kwart rearrangement (NKR) is a useful method for synthesizing <i>S</i>-aryl thiocarbamates from <i>O</i>-aryl thiocarbamates. Harsh temperature conditions are required, however, leading to substrate degradation and side reactions. Moreover, reactions using heteroaromatic substrates are quite rare. Herein, we report Bi(OTf)<sub>3</sub>-catalyzed NKR using heteroaromatic substrates under ambient temperature conditions. The reaction extended to not only aza-arene substrates but also thiophene substrates.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"65 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462966","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
Lewis Acid-Enabled Chemodivergent Cycloadditions of Donor–Acceptor Cyclopropanes with Indoline-2-Thiones
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1021/acs.joc.4c02791
Chen-Ying Zhai, Bing Zhao, Xue-Long Wang, Huai-Yan Liu, Bo Zhao, Yan Jiang
{"title":"Lewis Acid-Enabled Chemodivergent Cycloadditions of Donor–Acceptor Cyclopropanes with Indoline-2-Thiones","authors":"Chen-Ying Zhai, Bing Zhao, Xue-Long Wang, Huai-Yan Liu, Bo Zhao, Yan Jiang","doi":"10.1021/acs.joc.4c02791","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02791","url":null,"abstract":"Lewis acid-enabled reactions of donor–acceptor cyclopropanes (DACs) with indoline-2-thiones are reported. The reaction exhibits tunable annulation depending on the Lewis acid and the substituent at N1 of the indoline-2-thiones. With AlCl<sub>3</sub> as the Lewis acid and 1-isopropylindoline-2-thiones as reactants, a direct ring opening with DACs, followed by intramolecular nucleophilic addition/dehydration takes place leading to the formation of dihydro-2<i>H</i>-thiepino[2,3-<i>b</i>]indoles in moderate to good yields. Using Yb(OTf)<sub>3</sub> as promoter and 1-unsubstituted indoline-2-thiones as reactants, a (3 + 2) cycloaddition with DACs accompanied by sulfur rearrangement nucleophilic addition/dehydration takes place to give 3-indolyl-4,5-dihydrothiophenes in moderate yields. In addition, the synthetic transformation of 3-indolyl-4,5-dihydrothiophene to sulfone and indole-based axially chiral scaffolds further extends the synthetic utility and structural complexity.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"3 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462967","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 of l-Tryptophanamide and (S)-1-(Naphthalen-2′-yl)ethanamine-Based Marfey-Type Derivatives for Amino Acid Configurational Analysis: Diastereomeric Resolutions Directed by π–Cation Bonding
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1021/acs.joc.4c02882
Mariam N. Salib, Tadeusz F. Molinski
{"title":"Synthesis and Performance of l-Tryptophanamide and (S)-1-(Naphthalen-2′-yl)ethanamine-Based Marfey-Type Derivatives for Amino Acid Configurational Analysis: Diastereomeric Resolutions Directed by π–Cation Bonding","authors":"Mariam N. Salib, Tadeusz F. Molinski","doi":"10.1021/acs.joc.4c02882","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02882","url":null,"abstract":"The configurational analysis of amino acids (AAs) in natural product peptides, often containing nonproteinogenic AAs, is mostly carried out by the venerable Marfey’s method using a chiral derivatizing agent (CDA) 1-fluoro-2,4-dinitrophenyl-5-<span>l</span>-alaninamide (<span>l</span>-FDAA)─Marfey’s reagent─which undergoes <i>S</i><sub>N</sub>Ar reaction of the 1° amino group. The resulting AA-DAA derivatives are mostly well-separated by reversed-phase HPLC, but some DAA derivatives resist resolution. Here, we report the synthesis and characterization of two CDAs: <span>l</span>-FDTA (<b>4</b>) in which the <span>l</span>-alanine-derived auxiliary is replaced by <span>l</span>-tryptophanamide and (<i>S</i>)-FDNE (<b>3</b>) where the auxiliary is <i>S</i>-(6-methoxynaphth-2-yl)-1-ethylamine. Side-by-side comparisons of the two reagents were carried out by AA derivatization and reversed-phase HPLC analysis with variables such as organic solvent, additives, and the ionic strength of the mobile phase. <span>l</span>-DTA derivatives of <span>l</span>- and <span>d</span>-AAs were found to show superior HPLC performance and an improvement in resolutions. When incorporated into the mobile phase, the ammonium ion (NH<sub>4</sub><sup>+</sup>, 0–100 mM) showed a dramatic influence on differential retention times [Δ<i>t</i><sub>R</sub> = Δ<i>t</i><sub>R</sub><span>d</span> – Δ<i>t</i><sub>R</sub><span>l</span>] of several key AAs. We attributed the effect to π–cation interactions between the indole ring of DTA and the NH<sub>4</sub><sup>+</sup> counterion in the analyte, a hypothesis supported by <sup>1</sup>H NMR titrations and DFT calculations.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"6 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462968","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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