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Iron-Catalyzed Dearomatizing Reductive Cyclization of Arenes.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 Epub Date: 2025-01-31 DOI: 10.1021/acs.orglett.4c04680
Ling-Jie Song, Xiao-Dong Zhang, Zheng-Hao Jin, Ren-Xiao Liang, Yi-Xia Jia
{"title":"Iron-Catalyzed Dearomatizing Reductive Cyclization of Arenes.","authors":"Ling-Jie Song, Xiao-Dong Zhang, Zheng-Hao Jin, Ren-Xiao Liang, Yi-Xia Jia","doi":"10.1021/acs.orglett.4c04680","DOIUrl":"10.1021/acs.orglett.4c04680","url":null,"abstract":"<p><p>An efficient iron-catalyzed intramolecular dearomatizing reductive cyclization of arenes has been developed. By employing FeBr<sub>2</sub> as the catalyst, tripyridine as the ligand, and Mn powder as the reductant, a series of spiro-cyclohexadienes and dihydronaphthalenes were afforded in moderate to excellent yields with aryliodine-tethered benzyl <i>tert</i>-butyl carbonate or naphthalene derivatives as substrates. In addition, several synthetic transformations were conducted to demonstrate the utility of the reaction, and control experiments were carried out to gain insight into the mechanism.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"1390-1395"},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143062328","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
Total Synthesis of Dixiamycins A and B via a Late-Stage N-N Bond Formation under Visible Light Photoredox Catalysis.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 Epub Date: 2025-01-30 DOI: 10.1021/acs.orglett.5c00083
Rhituparna Nandi, Ranjit Murmu, Sreyashi Sadhukhan, Debopam Pal, Souvik Biswas, Bishnu Das, Alakesh Bisai
{"title":"Total Synthesis of Dixiamycins A and B via a Late-Stage N-N Bond Formation under Visible Light Photoredox Catalysis.","authors":"Rhituparna Nandi, Ranjit Murmu, Sreyashi Sadhukhan, Debopam Pal, Souvik Biswas, Bishnu Das, Alakesh Bisai","doi":"10.1021/acs.orglett.5c00083","DOIUrl":"10.1021/acs.orglett.5c00083","url":null,"abstract":"<p><p>Intermolecular oxidative N-N bond formation reactions are quite challenging and are largely uncharted. N-N linked dimeric indolosesquiterpene alkaloids represent an underexplored class of natural products, and strategies for direct dehydrogenative N-N bond formation are limited. Here, we have reported that a late-stage visible-light photoredox catalysis facilitates N-N bond formation, leading to the total syntheses of atropo-diastereomers dixiamycins A (<b>1a</b>) and B (<b>1b</b>).</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"1531-1536"},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143062410","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
Directing Group Enabled Ruthenium-Catalyzed Asymmetric Hydrogenation of Naphthalenes and Related Carbocyclic Aromatics.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 Epub Date: 2025-01-31 DOI: 10.1021/acs.orglett.5c00014
Mu-Wang Chen, Yi-Xuan Ding, Yong-Gui Zhou
{"title":"Directing Group Enabled Ruthenium-Catalyzed Asymmetric Hydrogenation of Naphthalenes and Related Carbocyclic Aromatics.","authors":"Mu-Wang Chen, Yi-Xuan Ding, Yong-Gui Zhou","doi":"10.1021/acs.orglett.5c00014","DOIUrl":"10.1021/acs.orglett.5c00014","url":null,"abstract":"<p><p>Among the aromatic carbocyclic rings, the highly regio- and enantioselective hydrogenation of nonsymmetrical naphthalenes has remained a long-standing challenge in asymmetric catalysis. Herein, we reporte an amide-directed asymmetric hydrogenation of nonsymmetrical naphthalenes with a ruthenium catalyst with up to 99% ee. This strategy was also successfully applied in the asymmetric hydrogenation of polycyclic aromatic hydrocarbons.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"1511-1516"},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143070780","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
Diverse Annulations of Alkyl(phenyl)phosphinic Chlorides and Imines.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 Epub Date: 2025-01-30 DOI: 10.1021/acs.orglett.4c04737
Mengyao Zhang, Hongguang Du, Jiaxi Xu
{"title":"Diverse Annulations of Alkyl(phenyl)phosphinic Chlorides and Imines.","authors":"Mengyao Zhang, Hongguang Du, Jiaxi Xu","doi":"10.1021/acs.orglett.4c04737","DOIUrl":"10.1021/acs.orglett.4c04737","url":null,"abstract":"<p><p>The reactivity of alkyl(aryl)phosphinic chlorides and imines was investigated in the presence of a base. The results indicated that allyl/benzyl(aryl)phosphinic chlorides gave rise to 1,2-azaphosphines (δ-phostims), while nonbenzylic alkyl(aryl)phosphinic chlorides produced the corresponding β-phosphinolactams (β-phostims) in their reaction with cyclic dibenzo[<i>b</i>,<i>f</i>][1,4]oxazepines, whereas steric electron-rich arylmethyl(aryl)phosphinic chlorides generated [2 + 2 + 2] annuloadducts in some cases. The current investigation provides useful insight into the reactivity of phosphinic chlorides and imines.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"1417-1421"},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143062303","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
Electrochemically Driven Ugi-Azide Reaction via C(sp3)-H Bond Activation of Tertiary Amines.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 Epub Date: 2025-01-31 DOI: 10.1021/acs.orglett.5c00163
Bin Song, Feng Zhao, Pengxiang Gao, Ruizong Wang, Xuehai Ju, Bingcheng Hu, Chong Zhang
{"title":"Electrochemically Driven Ugi-Azide Reaction via C(sp<sup>3</sup>)-H Bond Activation of Tertiary Amines.","authors":"Bin Song, Feng Zhao, Pengxiang Gao, Ruizong Wang, Xuehai Ju, Bingcheng Hu, Chong Zhang","doi":"10.1021/acs.orglett.5c00163","DOIUrl":"10.1021/acs.orglett.5c00163","url":null,"abstract":"<p><p>An electrochemically driven Ugi-azide reaction was established via C(sp<sup>3</sup>)-H bond activation of tertiary amines to prepare α-aminomethyl tetrazoles within 2.5 h under mild conditions with remarkable tolerance of various functional groups. Besides, this electrochemical strategy not only obviated the needs of iodine, metal, and exogenous oxidant but possessed potential applicability of convenient large-scale synthesis. Mechanistic studies indicated both the alkyl carbon-centered radical generated at the anode and intramolecular [3 + 2] cycloaddition are key factors for this strategy.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"1561-1567"},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143062313","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 Access to Chiral Benzylamines via Ni/Photoredox-Catalyzed Multicomponent Cross-Electrophile Coupling.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 Epub Date: 2025-01-30 DOI: 10.1021/acs.orglett.4c04859
Panting Cao, Wenhui Xiong, Tao Yang
{"title":"Modular Access to Chiral Benzylamines via Ni/Photoredox-Catalyzed Multicomponent Cross-Electrophile Coupling.","authors":"Panting Cao, Wenhui Xiong, Tao Yang","doi":"10.1021/acs.orglett.4c04859","DOIUrl":"10.1021/acs.orglett.4c04859","url":null,"abstract":"<p><p>A Ni/photoredox dual-catalyzed multicomponent cross-electrophile coupling of N-vinyl amides with (hetero)aryl halides and (2°, 3°)-alkyl redox-active esters in the presence of cheap reductant Hantzsch ester is reported here. This reductive protocol provides direct access to various synthetically challenging chiral α-arylamides in good yields and excellent enantioselectivities (up to 99% ee, with the majority exceeding 97% ee), which can be further derived into chiral primary and secondary amines. Preliminary experimental studies shed light on the potential catalytic pathways.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"1475-1480"},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143062405","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
Regioselective 1,4-Hydroamination of 1,3-Dienes by Photoredox/Cobalt Dual Catalysis.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 DOI: 10.1021/acs.orglett.5c00281
Pei-Ting Li, Quansheng Mou, Wei Yu
{"title":"Regioselective 1,4-Hydroamination of 1,3-Dienes by Photoredox/Cobalt Dual Catalysis.","authors":"Pei-Ting Li, Quansheng Mou, Wei Yu","doi":"10.1021/acs.orglett.5c00281","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00281","url":null,"abstract":"<p><p>Herein, we report a visible-light-driven and cobalt-mediated 1,4-hydroamination reaction of 1,3-dienes with arylmines as the nucleophiles. The reaction involves regioselective addition of [Co<sup>III</sup>]-H to 1,3-diene, followed by oxidation and nucleophilic substitution by amines. Using Ir(ppy)<sub>3</sub> as the photocatalyst enables the cobalt redox cycle to be implemented without using an external oxidant and hydride regent. This protocol can be applied as well to forge the carbon-oxygen and carbon-sulfur bonds in an analogous way.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143416845","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
Synthesis of Methyl Aprabiosaminide and 2-Hydroxyapramycin from Apramycin.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 DOI: 10.1021/acs.orglett.5c00168
Niteshlal Kasdekar, Michael R Spieker, Andrea Vasella, Sven N Hobbie, David Crich
{"title":"Synthesis of Methyl Aprabiosaminide and 2-Hydroxyapramycin from Apramycin.","authors":"Niteshlal Kasdekar, Michael R Spieker, Andrea Vasella, Sven N Hobbie, David Crich","doi":"10.1021/acs.orglett.5c00168","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00168","url":null,"abstract":"<p><p>We describe a protocol for the selective cleavage of the 2-deoxystreptamine ring from the structurally unusual aminoglycoside antibiotic apramycin, enabling for the first time the preparation of aprabiosamine derivatives. We further describe reglycosylation of the aprabiosamine core with a selectively protected optically pure streptamine derivative, giving, after deprotection, 2-hydroxyapramycin, the first apramycin derivative functionalized at the 2 position.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143412402","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
Double Hydride Transfer Enabled Substitution of All Hydrogens at α,β-Positions of Cyclic Amines: Access to α,β-Unsaturated Lactams
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-13 DOI: 10.1021/acs.orglett.5c00255
Ryosuke Yamagishi, Masahiro Anada, Shunsuke Sueki, Kosho Makino, Tatsuhiro Kojima, Tomoko Kawasaki-Takasuka, Keiji Mori
{"title":"Double Hydride Transfer Enabled Substitution of All Hydrogens at α,β-Positions of Cyclic Amines: Access to α,β-Unsaturated Lactams","authors":"Ryosuke Yamagishi, Masahiro Anada, Shunsuke Sueki, Kosho Makino, Tatsuhiro Kojima, Tomoko Kawasaki-Takasuka, Keiji Mori","doi":"10.1021/acs.orglett.5c00255","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00255","url":null,"abstract":"A one-shot substitution of all hydrogens at the α,β-positions of saturated cyclic amines was achieved. The key feature of this reaction is the sequential involvement of intra- and intermolecular redox processes. When <i>N</i>,<i>O</i>-acetals obtained through an internal redox process were treated with a catalytic amount of Zn(OTf)<sub>2</sub> and an excess amount of benzylidene barbiturates, three key transformations involving intermolecular redox process occurred successively to afford α,β-unsaturated lactams in moderate to good chemical yields.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"19 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143401631","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 Aminooxygenation of Enamides.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-13 DOI: 10.1021/acs.orglett.5c00005
Yong Yuan, Feng Zhang, Xincong Liu, Chunyan Bai, Hangfei Jiang, Xiazhen Bao, Dongsheng Ji, Congde Huo
{"title":"Electrochemical Aminooxygenation of Enamides.","authors":"Yong Yuan, Feng Zhang, Xincong Liu, Chunyan Bai, Hangfei Jiang, Xiazhen Bao, Dongsheng Ji, Congde Huo","doi":"10.1021/acs.orglett.5c00005","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00005","url":null,"abstract":"<p><p>Herein, we present an unprecedented electrochemical approach for aminooxygenation of enamides with azoles under transition-metal- and oxidizing-reagent-free conditions. This method affords 4-azolated oxazolines directly from readily available starting materials in up to 95% yield. Central to our success is the utilization of electrical energy as the primary driving force and NaBr as a mediator. Importantly, the resulting 4-azolated oxazolines exhibit potential utility as ligands (pyrazole-oxazoline ligands) in transition-metal-catalyzed reactions.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9,"publicationDate":"2025-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143412398","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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