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Photoredox/Copper Dual-Catalyzed Three-Component Perfluoroalkyl Trifluoromethylthiolation of Alkenes.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-20 DOI: 10.1021/acs.orglett.5c00289
Kang Guo, Shaomian Liu, Yutong Yang, Fang Xu, Yongchao Lu, Jiayi Shang, Aizhen Song
{"title":"Photoredox/Copper Dual-Catalyzed Three-Component Perfluoroalkyl Trifluoromethylthiolation of Alkenes.","authors":"Kang Guo, Shaomian Liu, Yutong Yang, Fang Xu, Yongchao Lu, Jiayi Shang, Aizhen Song","doi":"10.1021/acs.orglett.5c00289","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00289","url":null,"abstract":"<p><p>A new three-component 1,2-perfluoroalkyl trifluoromethylthiolation of alkenes via dual photoredox/copper catalysis has been established, affording a variety of C<sub><i>n</i></sub>F<sub>2<i>n</i>+1</sub>/CF<sub>3</sub>S-containing molecules under mild conditions in a redox-neutral manner. This protocol exhibits excellent functional group tolerance, broad compatibility with various alkenes and perfluoroalkyl iodides, and potential utility in the modification of bioactive molecules.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143456286","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 Radical Fluorosufonylation of Allyl Bromides
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-20 DOI: 10.1021/acs.orglett.5c00256
Bingcong Liu, Hui Liang, Yanju Lu, Shenlin Huang
{"title":"Electrochemical Radical Fluorosufonylation of Allyl Bromides","authors":"Bingcong Liu, Hui Liang, Yanju Lu, Shenlin Huang","doi":"10.1021/acs.orglett.5c00256","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00256","url":null,"abstract":"A radical fluorosulfonylation of allyl bromides was achieved under electroreductive conditions. This catalyst-free protocol employs mild conditions and enables straightforward access to a new and structurally diverse variety of previously inaccessible allyl sulfonyl fluorides. We have also illustrated the synthetic value of this method by performing scaled-up reactions and product derivatization.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"182 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143463023","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
Photocatalytic C–H Trifluoroethoxylation of (Hetero)arenes
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-20 DOI: 10.1021/acs.orglett.5c00383
Mingxi Chen, Jingjing Ling, Keguang Cheng, Quande Wang
{"title":"Photocatalytic C–H Trifluoroethoxylation of (Hetero)arenes","authors":"Mingxi Chen, Jingjing Ling, Keguang Cheng, Quande Wang","doi":"10.1021/acs.orglett.5c00383","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00383","url":null,"abstract":"The trifluoroethoxy group (OCH<sub>2</sub>CF<sub>3</sub>) is a valuable motif prevalent in pharmaceuticals and agrichemicals. Herein, we present a simple radical trifluoroethoxylation method that enables nondirected functionalization of C–H bonds of a broad array of substrates, providing access to (hetero)aryl trifluoroethyl ethers. The current protocol tolerates a variety of synthetically and pharmacologically relevant functional groups. Applicability is also demonstrated through the late-stage functionalization of biorelevant molecules and marketing drugs.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"3 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143463025","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 γ-Lactams via Palladium-Catalyzed C(sp3)–H Bond Activation of Alkyl Sulfonamides with Substituted Alkenes
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-20 DOI: 10.1021/acs.orglett.5c00152
Ananya Dutta, Masilamani Jeganmohan
{"title":"Synthesis of γ-Lactams via Palladium-Catalyzed C(sp3)–H Bond Activation of Alkyl Sulfonamides with Substituted Alkenes","authors":"Ananya Dutta, Masilamani Jeganmohan","doi":"10.1021/acs.orglett.5c00152","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00152","url":null,"abstract":"A methodology for the <i>γ</i>-butyrolactam scaffolds via ligand-enabled C(sp<sup>3</sup>)–H bond functionalization of sulfonamides with olefins has been demonstrated. The protocol has been found to be compatible with several activated and unactivated olefins, and the desired lactams were formed in excellent yields. A plausible mechanism has been described to account for the desired lactamization reaction as well as supported by mechanistic investigation including a <sup>1</sup>H NMR study and isolation of a palladacycle intermediate.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"30 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143463022","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
Ambient Temperature Cleavages of Amides in an Aqueous Medium for the Ipsilateral Effect of 1,8-Substituents on Naphthalene.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-20 DOI: 10.1021/acs.orglett.5c00122
Lunyu Ou, Hongyun Li, Weifeng Wang, Yufen Zhao, Hua Fu
{"title":"Ambient Temperature Cleavages of Amides in an Aqueous Medium for the Ipsilateral Effect of 1,8-Substituents on Naphthalene.","authors":"Lunyu Ou, Hongyun Li, Weifeng Wang, Yufen Zhao, Hua Fu","doi":"10.1021/acs.orglett.5c00122","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00122","url":null,"abstract":"<p><p>The selective release of a molecule in its native form from a constructed framework is very attractive in the chemical and biological fields. The amide bond is ubiquitous in biological and chemical systems. However, the cleavage of an unmodified typical amide is a great challenge because of its high level of stabilization. Here, couplings of 8-azido-1-naphthoic acid prepared by us with amines afforded 8-azido-1-naphthamides. Reductions of 8-azido in 8-azido-1-naphthamides with sodium sulfide yielded 8-amino-1-naphthamides, and then, fast intramolecular nucleophilic attack of 8-amino to carbonyl of 1-amido in the presence of silica gel as the additive afforded 2,3-benzo[<i>cd</i>]indol-2(1<i>H</i>)-one freeing amines in almost quantitative conversion rates for the ipsilateral effect of 1,8-substituents on naphthalene. Furthermore, this strategy was extended to the cleavages of esters (alkyl 8-azido-1-naphthoates) successfully. The cleavages of amides and esters were performed in an aqueous medium at room temperature with wide functional group tolerance and were suitable for gram-scale production.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143456281","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 Construction of a SeCF3-Substituted Stereocenter by CuH-Catalyzed Hydroboration of 1-SeCF3-Alkenes.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-20 DOI: 10.1021/acs.orglett.5c00330
Haruka Matsui, Yuki Kojima, Kosuke Yasui, Yuji Nishii, Koji Hirano
{"title":"Asymmetric Construction of a SeCF<sub>3</sub>-Substituted Stereocenter by CuH-Catalyzed Hydroboration of 1-SeCF<sub>3</sub>-Alkenes.","authors":"Haruka Matsui, Yuki Kojima, Kosuke Yasui, Yuji Nishii, Koji Hirano","doi":"10.1021/acs.orglett.5c00330","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00330","url":null,"abstract":"<p><p>A copper hydride (CuH)-catalyzed regio- and enantioselective hydroboration of 1-trifluoromethylseleno (SeCF<sub>3</sub>)-alkenes with H-Bpin has been developed. The regio- and enantioselective hydrocupration of an <i>in situ</i> generated CuH species is followed by a boration reaction to successfully construct a SeCF<sub>3</sub>- and Bpin-substituted chiral carbon center. The key to success is the appropriate choice of <i>t</i>Bu-modified biphosphine ligands, which enables an overwhelming high reaction efficiency.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143456282","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
Palladium-Catalyzed Intermolecular 1,3-Dienylation of Propargyl Esters Involving the Insertion of SO2
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-20 DOI: 10.1021/acs.orglett.5c00334
Haohao Jiang, Mengzhao Yu, Shuoshuo Zhang, Ling Jin, Yue Zhang, Xiaolei Huang
{"title":"Palladium-Catalyzed Intermolecular 1,3-Dienylation of Propargyl Esters Involving the Insertion of SO2","authors":"Haohao Jiang, Mengzhao Yu, Shuoshuo Zhang, Ling Jin, Yue Zhang, Xiaolei Huang","doi":"10.1021/acs.orglett.5c00334","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00334","url":null,"abstract":"A palladium-catalyzed three-component 1,3-dienylation of propargylic esters with DABSO and aryl iodides has been developed. This novel reductive cross-coupling reaction produces 2-sufonylated 1,3-dienes as single products in the presence of reductive metal Mn with high regio- and chemoselectivities. Control experiments demonstrated that the transformation may undergo a radical process.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"19 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143463024","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
Merging Photoexcited Nitroarenes with Lewis Acid Catalysis for the Anti-Markovnikov Oxidation of Alkenes.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-20 DOI: 10.1021/acs.orglett.5c00389
Joshua M Paolillo, Mahmoud R Saleh, Ethan W Junk, Marvin Parasram
{"title":"Merging Photoexcited Nitroarenes with Lewis Acid Catalysis for the Anti-Markovnikov Oxidation of Alkenes.","authors":"Joshua M Paolillo, Mahmoud R Saleh, Ethan W Junk, Marvin Parasram","doi":"10.1021/acs.orglett.5c00389","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00389","url":null,"abstract":"<p><p>Herein we describe the oxidation of alkenes to carbonyls and acetonides via the interplay of photoexcited nitroarenes and Lewis acid catalysis. A wide range of alkenes were oxidized to aldehyde and ketone products with anti-Markovnikov selectivity and to acetonides when acetone was employed as a co-solvent. Mechanistic studies support that Lewis acid coordination to the 1,3,2-dioxazolidine intermediate results in a 1,2-shift to generate carbonyl derivatives and a nucleophilic substitution pathway for the formation of acetonides.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143456285","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
Manganese(I)-Catalyzed Enantioselective Formal Anti-Markovnikov Hydroalkoxylation of Racemic Allylic Alcohols: A Borrowing Hydrogen Access
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-20 DOI: 10.1021/acs.orglett.5c00161
Shuai-Hu Liu, Faju Li, Yan-Mei He, Qing-Hua Fan
{"title":"Manganese(I)-Catalyzed Enantioselective Formal Anti-Markovnikov Hydroalkoxylation of Racemic Allylic Alcohols: A Borrowing Hydrogen Access","authors":"Shuai-Hu Liu, Faju Li, Yan-Mei He, Qing-Hua Fan","doi":"10.1021/acs.orglett.5c00161","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00161","url":null,"abstract":"An enantioselective manganese(I)-catalyzed formal anti-Markovnikov hydroalkoxylation of racemic allylic alcohols has been developed using a chiral N<sub>6</sub>-type macrocyclic ligand, affording a wide range of chiral γ-alkoxypropyl alcohols in high isolated yields with excellent enantioselectivities. The synthetic utility of this protocol was further proven by gram-scale synthesis of chiral γ-alkoxypropanol <b>3n</b> and derivatization of chiral γ-alkoxypropanol <b>3a</b> to a drug molecule, (<i>S</i>)-dapoxetine, for the treatment of premature ejaculation and erectile dysfunction. Mechanistic studies support that the reaction proceeds via a hydrogen-borrowing cascade reaction pathway.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"80 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462975","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
Phosphine-Based Porous Organic Polymer-Stabilized Palladium Nanoparticle Catalyst for the Regioselective Synthesis of Indenones
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-20 DOI: 10.1021/acs.orglett.5c00299
Pramod Kumar, Ayan Jati, Biplab Maji
{"title":"Phosphine-Based Porous Organic Polymer-Stabilized Palladium Nanoparticle Catalyst for the Regioselective Synthesis of Indenones","authors":"Pramod Kumar, Ayan Jati, Biplab Maji","doi":"10.1021/acs.orglett.5c00299","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00299","url":null,"abstract":"Phosphorus-embedded porous organic polymers (P-POPs) play a vital role in catalysis and sustainable chemical synthesis. This study uses an olefin-linked P-POP to stabilize Pd nanoparticles that catalyze Larock’s annulation to synthesize symmetrical indenones in high yields. Unsymmetric indenones were obtained with exclusive regioselectivities by employing an intramolecular dicarbofunctionalization of a modular alkyne. The approach addresses selectivity challenges in indenone synthesis and broadens the reaction scope by incorporation of aryl halides. The catalyst is robust and recyclable.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"3 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462980","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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