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Electronic Effects of Bidentate P,N-Ligands on the Elementary Steps of Au(I)/Au(III) Reactions Relevant to Cross-Coupling Chemistry
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-09 DOI: 10.1021/acs.orglett.4c0404510.1021/acs.orglett.4c04045
Joseph W. Treacy, Elaine Y. Chao, Grace E. Kunkel, Thomas Louis-Goff, James A. R. Tilden, Alexander M. Spokoyny*, Heather D. Maynard* and K. N. Houk*, 
{"title":"Electronic Effects of Bidentate P,N-Ligands on the Elementary Steps of Au(I)/Au(III) Reactions Relevant to Cross-Coupling Chemistry","authors":"Joseph W. Treacy,&nbsp;Elaine Y. Chao,&nbsp;Grace E. Kunkel,&nbsp;Thomas Louis-Goff,&nbsp;James A. R. Tilden,&nbsp;Alexander M. Spokoyny*,&nbsp;Heather D. Maynard* and K. N. Houk*,&nbsp;","doi":"10.1021/acs.orglett.4c0404510.1021/acs.orglett.4c04045","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04045https://doi.org/10.1021/acs.orglett.4c04045","url":null,"abstract":"<p >Oxidant-free Au(I)/Au(III)-catalyzed cross-coupling has been recently enabled by the use of bidentate <i>P</i>,<i>N</i>-ligands. To further develop these <i>P</i>,<i>N</i>-ligands, computational studies were performed to understand their effects on the oxidative addition of aryl iodide electrophiles with Au(I). Using this mechanistic understanding, six new electron-rich <i>P</i>,<i>N</i>-ligands were synthesized. The ligand exchange equilibrium and reductive elimination were then characterized by using a Au(III)-mediated <i>S</i>-arylation reaction. The results detailed herein provide new fundamental insights in Au(I)/Au(III) ligand design.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 50","pages":"10875–10879 10875–10879"},"PeriodicalIF":4.9,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.orglett.4c04045","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858708","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Triflic Acid-Mediated Chemoselective Indole C2-Heteroarylation of Peptide Tryptophan Residues by Triazine
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-09 DOI: 10.1021/acs.orglett.4c0410010.1021/acs.orglett.4c04100
Jian Li, Qi-Long Hu, Jia-Shu Liu and Xiao-Feng Xiong*, 
{"title":"Triflic Acid-Mediated Chemoselective Indole C2-Heteroarylation of Peptide Tryptophan Residues by Triazine","authors":"Jian Li,&nbsp;Qi-Long Hu,&nbsp;Jia-Shu Liu and Xiao-Feng Xiong*,&nbsp;","doi":"10.1021/acs.orglett.4c0410010.1021/acs.orglett.4c04100","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04100https://doi.org/10.1021/acs.orglett.4c04100","url":null,"abstract":"<p >Peptide modification provides opportunities to afford peptides with designed functions. Among the proteogenic amino acids, tryptophan represents an ideal and attractive target for peptide modification because of the exclusive chemical reactivity of its unique indole structure. Herein, we reported an indole C2 position-selective and transition-metal-free modification approach for indole derivatives and tryptophan-containing peptides by triazine derivatives via triflic acid activation and that the incorporated functional group could act as an orthogonal handle for further bioconjugation via an inverse electron demand Diels–Alder reaction.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 50","pages":"10928–10933 10928–10933"},"PeriodicalIF":4.9,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858712","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
Decarboxylative Coupling of Ketoacids with Allylic Acetates
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-09 DOI: 10.1021/acs.orglett.4c0351410.1021/acs.orglett.4c03514
Xiaoyu Zhang, Fanyi Hou, Yinlei Zhang, Bowen Li, Peizhong Xie* and Teck-Peng Loh*, 
{"title":"Decarboxylative Coupling of Ketoacids with Allylic Acetates","authors":"Xiaoyu Zhang,&nbsp;Fanyi Hou,&nbsp;Yinlei Zhang,&nbsp;Bowen Li,&nbsp;Peizhong Xie* and Teck-Peng Loh*,&nbsp;","doi":"10.1021/acs.orglett.4c0351410.1021/acs.orglett.4c03514","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03514https://doi.org/10.1021/acs.orglett.4c03514","url":null,"abstract":"<p >We developed a novel, metal-free catalytic system for synthesizing a broad range of itaconates using α-ketoacids and allylic acetate. This method, leveraging phosphine and Mes-Acr<sup>+</sup>(BF<sub>4</sub><sup>–</sup>) catalysts, has proven versatile, enabling the efficient itaconation of peptides, the synthesis of bioactive itaconates, and the preparation of an itaconate-based bio-orthogonal probe.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 50","pages":"10696–10701 10696–10701"},"PeriodicalIF":4.9,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858713","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
Copper-Catalyzed One-Pot Protocol for Reductive N-Arylation of Nitroarenes with (Hetero)aryl Chlorides in Water
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-09 DOI: 10.1021/acs.orglett.4c03753
Peng Hong, Lifang Wang, Xinhai Zhu, Manna Huang, Yiqian Wan
{"title":"Copper-Catalyzed One-Pot Protocol for Reductive N-Arylation of Nitroarenes with (Hetero)aryl Chlorides in Water","authors":"Peng Hong, Lifang Wang, Xinhai Zhu, Manna Huang, Yiqian Wan","doi":"10.1021/acs.orglett.4c03753","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03753","url":null,"abstract":"A novel protocol for the Cu-catalyzed reductive <i>N</i>-arylation of nitroarenes with (hetero)aryl chlorides in water has been realized. Combining <i>N</i>-(9<i>H</i>-carbazol-9-yl)-6-hydroxypicolinamide (<b>L2</b>) with oxalohydrazide is vital to realize the method at 90 °C with a loading of 5 mol % of Cu<sub>2</sub>O/<b>L2</b>. Various nitroarenes and aryl chlorides have been successfully coupled in good to excellent isolated yields. Further, two diarylamine-containing key intermediates, <b>3f</b> and <b>4u</b>, have been smoothly synthesized on a gram scale using this method.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"36 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142793668","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
Modular Total Synthesis and Antimycobacterial Activity of Rufomycins
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-09 DOI: 10.1021/acs.orglett.4c0416310.1021/acs.orglett.4c04163
Max J. Bedding, Bryton C. Forster, Andrew M. Giltrap, Maxwell T. Stevens, Leo Corcilius, Warwick J. Britton and Richard J. Payne*, 
{"title":"Modular Total Synthesis and Antimycobacterial Activity of Rufomycins","authors":"Max J. Bedding,&nbsp;Bryton C. Forster,&nbsp;Andrew M. Giltrap,&nbsp;Maxwell T. Stevens,&nbsp;Leo Corcilius,&nbsp;Warwick J. Britton and Richard J. Payne*,&nbsp;","doi":"10.1021/acs.orglett.4c0416310.1021/acs.orglett.4c04163","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04163https://doi.org/10.1021/acs.orglett.4c04163","url":null,"abstract":"<p >The rufomycins are a family of nonribosomal cyclic peptides isolated from the deep sea-dwelling <i>Streptomyces atratus.</i> Herein, we describe the total synthesis of six congeners in the rufomycin family. Synthesis was achieved through a modular solid-phase strategy, incorporating synthetic nonproteinogenic amino acids: <span>l</span>-2-amino-4-hexenoic acid, <i>tert-</i>prenyl-<span>l</span>-tryptophan (and related (<i>S</i>)-epoxide), and <i>N</i>-methyl-δ-hydroxy-<span>l</span>-leucine. Following macrolactamization, these peptides were further diversified through late-stage oxidation and secondary cyclization to furnish a library of six synthetic natural products. Rufomycins 4 and 22, bearing an unusual 6-hydroxypiperidin-2-one structural motif, exhibited impressive activity against the virulent H37Rv strain of <i>Mycobacterium tuberculosis</i> (MIC<sub>50</sub> = 350–670 nM).</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 50","pages":"10993–10998 10993–10998"},"PeriodicalIF":4.9,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858709","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 Rapid [18F]Trifluoromethyl Radiolabeling of Terminal Alkenes at Room Temperature
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-09 DOI: 10.1021/acs.orglett.4c04022
Xuefei Li, Lang Xie, Shun Huang, Xin Guo, Jian Yang, Liang Zhao, Dezhi Yang, Guojin Zhang, Chun-Yang He
{"title":"Late-Stage Rapid [18F]Trifluoromethyl Radiolabeling of Terminal Alkenes at Room Temperature","authors":"Xuefei Li, Lang Xie, Shun Huang, Xin Guo, Jian Yang, Liang Zhao, Dezhi Yang, Guojin Zhang, Chun-Yang He","doi":"10.1021/acs.orglett.4c04022","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04022","url":null,"abstract":"We report an efficient, metal-free method for late-stage rapid [<sup>18</sup>F]trifluoromethyl radiolabeling of terminal alkenes at room temperature. Utilizing 3,3-difluoroallyl sulfonium salts as precursors, the process achieves high radiochemical yields (up to 94 ± 2%) in just 30 s, with excellent functional group tolerance. This method offers a simplified and efficient pathway to produce [<sup>18</sup>F]trifluoromethylated terminal alkene compounds, enabling their application in PET imaging and expanding the chemical space for drug discovery.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142793672","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
Electronic Effects of Bidentate P,N-Ligands on the Elementary Steps of Au(I)/Au(III) Reactions Relevant to Cross-Coupling Chemistry
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-09 DOI: 10.1021/acs.orglett.4c04045
Joseph W. Treacy, Elaine Y. Chao, Grace E. Kunkel, Thomas Louis-Goff, James A. R. Tilden, Alexander M. Spokoyny, Heather D. Maynard, K. N. Houk
{"title":"Electronic Effects of Bidentate P,N-Ligands on the Elementary Steps of Au(I)/Au(III) Reactions Relevant to Cross-Coupling Chemistry","authors":"Joseph W. Treacy, Elaine Y. Chao, Grace E. Kunkel, Thomas Louis-Goff, James A. R. Tilden, Alexander M. Spokoyny, Heather D. Maynard, K. N. Houk","doi":"10.1021/acs.orglett.4c04045","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04045","url":null,"abstract":"Oxidant-free Au(I)/Au(III)-catalyzed cross-coupling has been recently enabled by the use of bidentate <i>P</i>,<i>N</i>-ligands. To further develop these <i>P</i>,<i>N</i>-ligands, computational studies were performed to understand their effects on the oxidative addition of aryl iodide electrophiles with Au(I). Using this mechanistic understanding, six new electron-rich <i>P</i>,<i>N</i>-ligands were synthesized. The ligand exchange equilibrium and reductive elimination were then characterized by using a Au(III)-mediated <i>S</i>-arylation reaction. The results detailed herein provide new fundamental insights in Au(I)/Au(III) ligand design.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"121 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142793671","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
Oxidations of (2,2′-Diphenyl)ethylidene-Bridged Porphyrin Dimers
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-09 DOI: 10.1021/acs.orglett.4c04063
Ye Xiao, Jiale Tang, Ling Xu, Yutao Rao, Bangshao Yin, Mingbo Zhou, Atsuhiro Osuka, Jianxin Song
{"title":"Oxidations of (2,2′-Diphenyl)ethylidene-Bridged Porphyrin Dimers","authors":"Ye Xiao, Jiale Tang, Ling Xu, Yutao Rao, Bangshao Yin, Mingbo Zhou, Atsuhiro Osuka, Jianxin Song","doi":"10.1021/acs.orglett.4c04063","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04063","url":null,"abstract":"Oxidation reactions of (2,2′-diphenyl)ethylidene-bridged porphyrin dimers were examined for the synthesis of (2,2′-diphenyl)ethylidene-inserted porphyrin arch tape dimers. These reactions provided, in addition to the target arch tape dimers, unexpected products such as a bicyclo[3.3.0]octane-fused porphyrin dimer, a (2,2′-fluorenyl)ethylidene-inserted porphyrin arch tape dimer, and a <i>meso</i>- and <i>ortho</i>-phenyl-linked free base dimer, depending upon the substrate and reaction conditions, demonstrating the high promise of these porphyrin substrates. The target arch tape dimers, which were synthesized by the oxidation with DDQ and CF<sub>3</sub>SO<sub>3</sub>H, exhibit red-shifted and enhanced Q-bands and small electrochemical HOMO–LUMO gaps, indicating effective conjugation.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"18 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142793673","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
Radical Alkylcyanation of 1,6-Enynes with Isonitriles as Bifunctional Reagents
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-09 DOI: 10.1021/acs.orglett.4c03744
Zhonghou Huang, Jian Qin, Yuntong Hu, Shengqing Zhu, Lingling Chu
{"title":"Radical Alkylcyanation of 1,6-Enynes with Isonitriles as Bifunctional Reagents","authors":"Zhonghou Huang, Jian Qin, Yuntong Hu, Shengqing Zhu, Lingling Chu","doi":"10.1021/acs.orglett.4c03744","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03744","url":null,"abstract":"We report a radical cyano-cyclization of 1,6-enynes with isonitriles via photochemically driven nickel catalysis, forging alkenyl nitrile-tethered γ-lactams under mild conditions. This reaction leverages the photoexcitation of <i>in situ</i> generated nickel (isonitrile) species to facilitate isonitriles serving as alkyl radical precursors and cyanide sources. The reaction accommodates a wide range of substrates, exhibiting excellent regioselectivity and <i>Z</i>/<i>E</i> stereoselectivity.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"37 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142793761","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
Isolation and Biomimetic Semisynthesis of Hyperzrones A and B, Two Nor-Polycyclic Polyprenylated Acylphloroglucinols with a Characteristic Cyclobutane Moiety, from Hypericum beanii
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-09 DOI: 10.1021/acs.orglett.4c0413510.1021/acs.orglett.4c04135
Xue-Yan Li, Lv-Jun Zhang, Yue-You Yang, Wei-Jia Lu, Sheng-Tao Ye, Hao Zhang, Ling-Yi Kong* and Wen-Jun Xu*, 
{"title":"Isolation and Biomimetic Semisynthesis of Hyperzrones A and B, Two Nor-Polycyclic Polyprenylated Acylphloroglucinols with a Characteristic Cyclobutane Moiety, from Hypericum beanii","authors":"Xue-Yan Li,&nbsp;Lv-Jun Zhang,&nbsp;Yue-You Yang,&nbsp;Wei-Jia Lu,&nbsp;Sheng-Tao Ye,&nbsp;Hao Zhang,&nbsp;Ling-Yi Kong* and Wen-Jun Xu*,&nbsp;","doi":"10.1021/acs.orglett.4c0413510.1021/acs.orglett.4c04135","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04135https://doi.org/10.1021/acs.orglett.4c04135","url":null,"abstract":"<p >Hyperzrones A (<b>1</b>) and B (<b>2</b>), two unprecedented <i>nor</i>-polycyclic polyprenylated acylphloroglucinols with a characteristic cyclobutane moiety, were discovered from <i>Hypericum beanii</i>. Their structures were determined by extensive spectroscopic analysis, X-ray crystallography, and quantum chemical calculation methods. A bioinspired semisynthesis of <b>1</b> and <b>2</b> was achieved from the natural precursor hypercalin B (<b>3</b>), featuring a Favorskii-type rearrangement and a visible-light-mediated [2 + 2] photocycloaddition. Several diverse derivatives were also obtained, providing a compound library for biological studies.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 50","pages":"10964–10969 10964–10969"},"PeriodicalIF":4.9,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858707","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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