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Near-Infrared-Light-Induced Iron(I) Dimer Enabled Abstraction of Ester Group from Cycloketone Oxime Esters
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-03-20 DOI: 10.1021/acs.orglett.5c00701
Xiao-Di Su, Xue-Ning Li, Qiang Liu, Zhu-Sheng Yang, Zhi-Xiang Wang, Xiang-Yu Chen
{"title":"Near-Infrared-Light-Induced Iron(I) Dimer Enabled Abstraction of Ester Group from Cycloketone Oxime Esters","authors":"Xiao-Di Su, Xue-Ning Li, Qiang Liu, Zhu-Sheng Yang, Zhi-Xiang Wang, Xiang-Yu Chen","doi":"10.1021/acs.orglett.5c00701","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00701","url":null,"abstract":"Photoinduced dimeric metal complexes have been extensively utilized in halogen atom transfer (XAT) reactions. In this study, we successfully achieved the abstraction of ester group from cyclobutanone oxime esters via iron(I)-dimer catalysis under near-infrared (NIR) light (730 nm) excitation, enabling the efficient synthesis of cyanoalkylated alkenes, quinazolinones, and 3,3-disubstituted oxindoles. Mechanistic investigations confirmed the NIR-induced functional group abstraction process.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143660720","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
Asymmetric Synthesis of CF3-Substituted β-Hydroxyketones and 1,3-Diols by Engineered Ketoreductases
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-03-20 DOI: 10.1021/acs.orglett.5c00685
Yangyang Li, Sizhe Yu, Yingqian Jiang, Chenming Huang, Jingxue Zhu, Jiaxiang Lv, Jiaqi Wang, Song You, Bin Qin
{"title":"Asymmetric Synthesis of CF3-Substituted β-Hydroxyketones and 1,3-Diols by Engineered Ketoreductases","authors":"Yangyang Li, Sizhe Yu, Yingqian Jiang, Chenming Huang, Jingxue Zhu, Jiaxiang Lv, Jiaqi Wang, Song You, Bin Qin","doi":"10.1021/acs.orglett.5c00685","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00685","url":null,"abstract":"Chiral CF<sub>3</sub>-substituted β-hydroxy ketones and 1,3-diols were prepared via the ketoreductase-catalyzed asymmetric reduction of the corresponding benzoyl trifluoroacetones. The variants of two ketoreductases, LfSDR1 and CgKR1, were screened or engineered for stereocomplementary synthesis of CF<sub>3</sub>-substituted β-hydroxy ketones with up to &gt;99% conversions and up to &gt;99% enantiomeric excess (ee) values. In addition, the cascade reduction or one pot reduction of diketones could afford the CF<sub>3</sub>-substituted 1,3-diols with up to &gt;99% ratios and &gt;99% ee values.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"19 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143661023","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 Fluorination of Thiophene-Based Heterocycles for Modulation of Multiple Physical Properties in Organic Semiconductors
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-03-20 DOI: 10.1021/acs.orglett.5c00133
Seung Un Ryu, Jaehyoung Koo, Taehyun Kim, Chanhyeok Kim, Taiho Park, Minjun Kim
{"title":"Regioselective Fluorination of Thiophene-Based Heterocycles for Modulation of Multiple Physical Properties in Organic Semiconductors","authors":"Seung Un Ryu, Jaehyoung Koo, Taehyun Kim, Chanhyeok Kim, Taiho Park, Minjun Kim","doi":"10.1021/acs.orglett.5c00133","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00133","url":null,"abstract":"Thiophene-based derivatives are cost-effective and promising electron-donating units in high-performance π-conjugated materials for organic electronics. Fluorination is crucial for modulating their electronic and structural properties; however, few studies have been conducted due to synthetic challenges. We developed a fluorination method that enables regioselective fluorination of thiophene-based heterocycles. Our comparative study revealed that the position and number of fluorine atoms fine-tune molecular orbital energies and interactions, providing valuable insights for organic semiconductor applications.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"89 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143666452","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
Gold-Catalyzed Intermolecular Assembly of Donor and Acceptor Fragments for [1,5]-Hydride Migrations
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-03-20 DOI: 10.1021/acs.orglett.5c00816
Xiao-Qian Zhang, Ningbo Li, Yongliang Zhang, Youliang Wang
{"title":"Gold-Catalyzed Intermolecular Assembly of Donor and Acceptor Fragments for [1,5]-Hydride Migrations","authors":"Xiao-Qian Zhang, Ningbo Li, Yongliang Zhang, Youliang Wang","doi":"10.1021/acs.orglett.5c00816","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00816","url":null,"abstract":"The [1,n]-hydride migration reactions represent one of the most powerful techniques to functionalize C(sp<sup>3</sup>)–H bonds and to rapidly construct molecular complexities. However, their substrates usually required multiple steps to prepare in advance. Herein, we developed a gold-catalyzed intermolecular coupling of hydride-donor-containing nucleophiles (amines) and hydride-acceptor-containing alkynes (1,3-diynamides) for cascade [1,5]-hydride migrations. Control experiments revealed the role of the dichloroethane solvent and the unexpected involvement of protonated anilines in promoting [1,5]-hydride migrations.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"46 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143666370","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
Cu-Catalyzed Enantioselective S-Arylation of Sulfenamides Enabled by Confined Ligands
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-03-20 DOI: 10.1021/acs.orglett.5c00132
Xiao-Bao Wu, Yue Shen, Hua-Jie Jiang, Liu-Zhu Gong
{"title":"Cu-Catalyzed Enantioselective S-Arylation of Sulfenamides Enabled by Confined Ligands","authors":"Xiao-Bao Wu, Yue Shen, Hua-Jie Jiang, Liu-Zhu Gong","doi":"10.1021/acs.orglett.5c00132","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00132","url":null,"abstract":"Chiral sulfilimines, aza analogues of sulfoxides, are essential in natural products and pharmaceuticals, highlighting the importance of their synthesis in asymmetric catalysis. However, efficient approaches for synthesizing chiral diaryl sulfilimines are still rare and challenging, particularly for those with two sterically similar aryl groups. Herein, we present a mild and efficient protocol for generating diverse enantioenriched diaryl and aryl alkyl sulfilimines via copper-catalyzed enantioselective S-arylation of <i>N</i>-acyl sulfenamides with diaryliodonium salts. A bulky PyBox ligand is crucial for stereocontrol, delivering various sulfilimines with up to 95% ee (51 examples).","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"183 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143661020","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
3-Oxabicyclo[3.1.1]heptanes as Isosteres of meta-Substituted Benzene Rings
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-03-20 DOI: 10.1021/acs.orglett.5c00646
Jennifer Morvan, Evelien Renders, Peter J. J. A. Buijnsters, Pavel Ryabchuk
{"title":"3-Oxabicyclo[3.1.1]heptanes as Isosteres of meta-Substituted Benzene Rings","authors":"Jennifer Morvan, Evelien Renders, Peter J. J. A. Buijnsters, Pavel Ryabchuk","doi":"10.1021/acs.orglett.5c00646","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00646","url":null,"abstract":"Replacement of the aromatic rings in drug candidates with isosteric rigid sp<sup>3</sup>-rich scaffolds can improve physicochemical properties, increase the chance of progressing the molecule in development, and open new chemical space. Isosteres of <i>meta</i>-substituted benzenes remain challenging due to the difficulty of mimicking the exit vector angles and bond distances. Herein, we report the synthesis of 1,5-disubstituted 3-oxabicyclo[3.1.1]heptanes (oxa-BCHeps), which can serve as saturated isosteres of <i>meta</i>-substituted phenyl rings with a similar geometric arrangement. This structural motif can be obtained under mild reaction conditions via acid-mediated isomerization of (2-oxaspiro[3.3]heptan-6-yl)methanols using catalytic quantities of pyridinium chloride (PyrHCl). We demonstrate the utility of this methodology by preparing various building blocks for use in medicinal chemistry and incorporating 3-oxa-BCHep into the anticancer drug sonidegib, improving its physicochemical properties, such as permeability, metabolic stability, and solubility.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"8 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143666367","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
Iron Porphyrins and Iron Salens as Highly Enantioselective Catalysts for the Ring-Expansion Reaction of Epoxides to Tetrahydrofurans
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-03-20 DOI: 10.1021/acs.orglett.5c00767
Mehmet Ulutürk, Mehmet Göllü, Tahir Tilki, Erkan Ertürk
{"title":"Iron Porphyrins and Iron Salens as Highly Enantioselective Catalysts for the Ring-Expansion Reaction of Epoxides to Tetrahydrofurans","authors":"Mehmet Ulutürk, Mehmet Göllü, Tahir Tilki, Erkan Ertürk","doi":"10.1021/acs.orglett.5c00767","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00767","url":null,"abstract":"Iron porphyrins have been found to be efficient catalysts for the ring-expansion reaction of epoxides with alkenes to give the corresponding tetrahydrofurans; very low loadings (down to 1 mol %) are sufficient to achieve high yields (up to 98%). Additionally, an iron(III) salen complex based on the axially chiral 1,1-binaphthalene backbone has been shown to catalyze the reaction with high enantioselectivity (<i>e.g</i>., 92% <i>ee</i> for calyxolane A).","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"731 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143660654","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 Syntheses of (+)-Aigialospirol and (+)-7′,8′-Dihydroaigialospirol by a One-Pot Stepwise Approach
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-03-20 DOI: 10.1021/acs.orglett.5c00484
Atsushi Nakayama, Hidemitsu Yamanaka, Rika Yamasaki, Naoki Hashimoto, Tetsuro Shinada
{"title":"Total Syntheses of (+)-Aigialospirol and (+)-7′,8′-Dihydroaigialospirol by a One-Pot Stepwise Approach","authors":"Atsushi Nakayama, Hidemitsu Yamanaka, Rika Yamasaki, Naoki Hashimoto, Tetsuro Shinada","doi":"10.1021/acs.orglett.5c00484","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00484","url":null,"abstract":"(+)-Aigialospirol and (+)-7′,8′-dihydroaigialospirol are known to be spiroketal polyketide-type natural products isolated from mangrove-derived fungus <i>Aigialus parvus</i> BCC 5311. These polyketides are structurally characterized by fusing resorcylic acid lactone and spiroketal moieties containing six asymmetric carbon centers. In this paper, we describe concise and stereoselective syntheses of these natural products based on biosynthesis-inspired transformation in nine steps. The total syntheses are highlighted by a one-pot stepwise synthesis involving (i) stereoselective lactone ring formation from a chiral epoxide, (ii) reduction of alkyne, (iii) global deprotection, and (iv) spiroketal formation, which are performed in the final step of the total synthesis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"37 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143661021","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
Near-Infrared-Light-Induced Iron(I) Dimer Enabled Abstraction of Ester Group from Cycloketone Oxime Esters
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-03-20 DOI: 10.1021/acs.orglett.5c0070110.1021/acs.orglett.5c00701
Xiao-Di Su, Xue-Ning Li, Qiang Liu, Zhu-Sheng Yang*, Zhi-Xiang Wang* and Xiang-Yu Chen*, 
{"title":"Near-Infrared-Light-Induced Iron(I) Dimer Enabled Abstraction of Ester Group from Cycloketone Oxime Esters","authors":"Xiao-Di Su,&nbsp;Xue-Ning Li,&nbsp;Qiang Liu,&nbsp;Zhu-Sheng Yang*,&nbsp;Zhi-Xiang Wang* and Xiang-Yu Chen*,&nbsp;","doi":"10.1021/acs.orglett.5c0070110.1021/acs.orglett.5c00701","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00701https://doi.org/10.1021/acs.orglett.5c00701","url":null,"abstract":"<p >Photoinduced dimeric metal complexes have been extensively utilized in halogen atom transfer (XAT) reactions. In this study, we successfully achieved the abstraction of ester group from cyclobutanone oxime esters via iron(I)-dimer catalysis under near-infrared (NIR) light (730 nm) excitation, enabling the efficient synthesis of cyanoalkylated alkenes, quinazolinones, and 3,3-disubstituted oxindoles. Mechanistic investigations confirmed the NIR-induced functional group abstraction process.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 12","pages":"3043–3047 3043–3047"},"PeriodicalIF":4.9,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143713984","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 and Stability of o-Carborane-Fused Phospholes
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-03-20 DOI: 10.1021/acs.orglett.5c00376
Caixia Jia, Lili Wang, Zheng Duan
{"title":"Synthesis and Stability of o-Carborane-Fused Phospholes","authors":"Caixia Jia, Lili Wang, Zheng Duan","doi":"10.1021/acs.orglett.5c00376","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00376","url":null,"abstract":"Herein, we report that ArLi, formed in situ through the Li/Br exchange between aryl bromide and <i>n</i>-butyllithium, can undergo rapid intramolecular Li/H(C<sub>cage</sub>–H) exchange to functionalize <i>o</i>-carboranes. Based on this observation, a dual C–H lithiation reaction of 2- or 3-<i>o</i>-carboryl benzothiophenes was developed, and a series of <i>o</i>-carborane-fused phospholes were synthesized by the reaction of dilithio compounds with chlorophosphine. This reaction is simple with high chemical selectivity and medium to high yields. It is also be applied to the furan derivative. Stability studies demonstrated that these <i>o</i>-carborane-fused phosphole derivatives are stable in both trivalent and coordination states for phosphorus. In contrast, their oxides are sensitive to moisture in air and are susceptible to attack by nucleophiles, leading to the breakage of the C<sub>cage</sub>-P bond. Computational results indicate that the newly generated phosphole rings have weak aromaticity.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"37 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143666363","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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