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Application of Lead-Free Metal Halide Perovskite Heterojunctions for the Carbohalogenation of C–C Multiple Bonds
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-01 DOI: 10.1021/acs.orglett.5c00780
Camilla Callegari, Costanza Tedesco, Alessia Corbo, Mirko Prato, Lorenzo Malavasi, Davide Ravelli
{"title":"Application of Lead-Free Metal Halide Perovskite Heterojunctions for the Carbohalogenation of C–C Multiple Bonds","authors":"Camilla Callegari, Costanza Tedesco, Alessia Corbo, Mirko Prato, Lorenzo Malavasi, Davide Ravelli","doi":"10.1021/acs.orglett.5c00780","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00780","url":null,"abstract":"A graphitic carbon nitride/lead-free double perovskite heterojunction (<i>g</i>-C<sub>3</sub>N<sub>4</sub>/Cs<sub>2</sub>AgBiCl<sub>6</sub>) has been adopted as a heterogeneous photocatalyst under visible light irradiation. The employed material enabled the atom transfer radical addition-type carbohalogenation of multiple C–C bonds, including (internal) alkenes and alkynes, with alkyl halides. The protocol showed a remarkable functional group tolerance, compatible with the late-stage functionalization of natural and pharmaceutical derivatives, and could be easily scaled up, delivering &gt;1 g of the desired products.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"66 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143758482","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
Visible-Light Mediated, Dual-Catalysis Enabled Allylic Difluoroalkylation via Halogen Atom Transfer
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-01 DOI: 10.1021/acs.orglett.5c00726
Shivani Arora, Pragya Katiyar, Tavinder Singh, Anand Singh
{"title":"Visible-Light Mediated, Dual-Catalysis Enabled Allylic Difluoroalkylation via Halogen Atom Transfer","authors":"Shivani Arora, Pragya Katiyar, Tavinder Singh, Anand Singh","doi":"10.1021/acs.orglett.5c00726","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00726","url":null,"abstract":"A visible-light-mediated protocol employing a halogen atom transfer strategy (XAT) has been developed for the synthesis of homoallylic difluorinated compounds. Employing a dual-catalysis reactivity manifold, which includes a cobaloxime catalyst, the reaction occurs without exogenous oxidant and under mild conditions. The applicability of unactivated olefins, a wide variety of halogenated precursors, and access to a diverse family of difluoromethylated molecular architectures are the highlights of this method.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"73 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745153","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
Recyclable Porous Organic Polymer-Supported Single-Atom Ruthenium Catalyst for Strong Si–F Bond Activation: Catalytic Si–F/Si–H and Si–F/Si–O Cross-Coupling Reactions
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-01 DOI: 10.1021/acs.orglett.5c00851
Shanshan Xu, Zhenning Sun, Juanjuan Zheng, Ruxin Jin, Ping Li, Feng Xie, Chenggang Ci, Bin Li
{"title":"Recyclable Porous Organic Polymer-Supported Single-Atom Ruthenium Catalyst for Strong Si–F Bond Activation: Catalytic Si–F/Si–H and Si–F/Si–O Cross-Coupling Reactions","authors":"Shanshan Xu, Zhenning Sun, Juanjuan Zheng, Ruxin Jin, Ping Li, Feng Xie, Chenggang Ci, Bin Li","doi":"10.1021/acs.orglett.5c00851","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00851","url":null,"abstract":"Developing efficient methods for strong Si–F σ-bond activation is very important in organosilicon chemistry. We report the preparation of a novel porous organic polymer (POP)-supported single-atom Ru catalyst (POPs-Ru SACs) that was successfully applied in catalytic strong Si–F/Si–H and Si–F/Si–O cross-coupling reactions. Various disiloxanes with functional group tolerance were produced under mild conditions. Furthermore, the POPs-Ru SACs catalyst exhibited excellent recyclability for Si–F and Si–H cross-coupling reactions. Density functional theory calculations were performed to verify the mechanism of POPs-Ru SACs-catalyzed Si–F/Si–H cross-coupling reactions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"183 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143758483","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 Multi-Atom Insertion of Esters via Rh-Catalyzed Ring Opening of Oxabicyclic Alkenes
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-01 DOI: 10.1021/acs.orglett.5c00971
Guorong Xiao, Yixiang Chen, Ziyi Wan, Duanyang Kong
{"title":"Asymmetric Multi-Atom Insertion of Esters via Rh-Catalyzed Ring Opening of Oxabicyclic Alkenes","authors":"Guorong Xiao, Yixiang Chen, Ziyi Wan, Duanyang Kong","doi":"10.1021/acs.orglett.5c00971","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00971","url":null,"abstract":"Precise skeletal manipulation involving insertion, deletion, and replacement has garnered considerable attention within the synthetic chemistry community. Among these processes, multi-atom insertion reactions in acyclic compounds remain a formidable challenge, primarily due to the low efficiency of fragment recapture after cleavage, which results from the lack of substrate-specific proximity during the reconstruction stage. Here, we report an asymmetric multi-atom insertion reaction of esters via Rh-catalyzed ring opening of oxabicyclic alkenes, achieving excellent regio-, diastereo-, and enantioselectivity. This approach enables the efficient and rapid construction of a molecular library of esters with a chiral hydroxy-dihydronaphthalene scaffold, showcasing an atom-efficient reaction. Detailed density functional theory calculations reveal key mechanistic features and the stereoselectivity-determining model of this transformation.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"58 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143758486","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
Nickel-Catalyzed 1,1-Carboboration of Polysubstituted Internal Alkenes
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-01 DOI: 10.1021/acs.orglett.5c00654
Tong Yao, Shiyang Wang, Yu Liu, Guoyin Yin, Yangyang Li
{"title":"Nickel-Catalyzed 1,1-Carboboration of Polysubstituted Internal Alkenes","authors":"Tong Yao, Shiyang Wang, Yu Liu, Guoyin Yin, Yangyang Li","doi":"10.1021/acs.orglett.5c00654","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00654","url":null,"abstract":"Herein, we report a nickel-catalyzed 1,1-carboboration of di- and trisubstituted alkenyl boronates through a chain-walking strategy. This reaction effectively addresses the polarity-mismatch problem via ligand control, enabling the coupling of various carbon-based electrophiles while accommodating a broad range of functional groups. The approach yields diverse tetrasubstituted carbon <i>gem</i>-diboronate derivatives with exceptional regioselectivity. The synthetic utility of this method is further demonstrated through the concise synthesis of high-value bioactive molecules.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"19 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745241","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-Catalyzed Site-Selective Bromination of Benzylic C(sp3)–H Bonds
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-01 DOI: 10.1021/acs.orglett.5c00864
Guangyi Zhang, Zihao Xu, Bing Han, Yuge Ji, Shengying Li, Meijuan Zhou, Min Cao, Xiaolong Yu, Lei Liu
{"title":"Iron-Catalyzed Site-Selective Bromination of Benzylic C(sp3)–H Bonds","authors":"Guangyi Zhang, Zihao Xu, Bing Han, Yuge Ji, Shengying Li, Meijuan Zhou, Min Cao, Xiaolong Yu, Lei Liu","doi":"10.1021/acs.orglett.5c00864","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00864","url":null,"abstract":"An iron-catalyzed chemo- and site-selective benzylic C–H bromination has been described. The practical approach uses the C–H substrate as the limiting reagent and commercially available iron(II) bromide at a loading of 1 mol % as the catalyst without the involvement of any extrinsic ligand. The simple and mild reaction can be readily scaled up to gram quantity with good functional group tolerance, offering a convenient route for the late-stage diversification of complex bioactive natural products and pharmaceutical molecules through sequential benzylic C–H bromination.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"32 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143758485","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 and Determination of the Absolute Configuration of Shodoamide C: An Amphotericin B Potentiator against Candida albicans
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-01 DOI: 10.1021/acs.orglett.5c01017
Shogo Ueki, Akihiro Hirata, Akiho Yagi, Masahiro Iwahori, Hiroshi Tomoda, Ryuji Uchida, Tohru Nagamitsu, Masaki Ohtawa
{"title":"Total Synthesis and Determination of the Absolute Configuration of Shodoamide C: An Amphotericin B Potentiator against Candida albicans","authors":"Shogo Ueki, Akihiro Hirata, Akiho Yagi, Masahiro Iwahori, Hiroshi Tomoda, Ryuji Uchida, Tohru Nagamitsu, Masaki Ohtawa","doi":"10.1021/acs.orglett.5c01017","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01017","url":null,"abstract":"The total synthesis and structural determination of shodoamide C (<b>1</b>), a compound that enhances the activity of amphotericin B against <i>Candida albicans</i>, have been achieved. A synthetic strategy for compound <b>1</b> facilitated the efficient synthesis of all 16 stereoisomers, allowing for the identification of the four previously unknown stereocenters of <b>1</b> through the chiral recycle HPLC analyses. All stereoisomers of <b>1</b> showed similar activity, indicating that their stereochemistries minimally influenced it.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"18 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143758489","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
Organometallic Reagent-Free Iron-Catalyzed C–Cl Bond Activation of Aryl Chlorines
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-01 DOI: 10.1021/acs.orglett.5c00877
Leifeng Yuan, Wenli Zhuang, Zemin Wang, Xiaowei Li, Cong Shi, Xiangqian Li, Dayong Shi
{"title":"Organometallic Reagent-Free Iron-Catalyzed C–Cl Bond Activation of Aryl Chlorines","authors":"Leifeng Yuan, Wenli Zhuang, Zemin Wang, Xiaowei Li, Cong Shi, Xiangqian Li, Dayong Shi","doi":"10.1021/acs.orglett.5c00877","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00877","url":null,"abstract":"The formation of C–C and C–S bonds is fundamentally important for the production of pharmaceuticals, biologically active molecules, and organic natural products. Herein, we report an unprecedented iron-catalyzed process for C–C and C–S bond coupling to achieve the 1,2-arylthiolation of alkenes. This process proceeds efficiently without the use of organometallic reagents and features readily available starting materials, a broad substrate scope, and simple reaction conditions","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"16 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745191","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 Nickel-Catalyzed Hydrotrifluoroalkylation of Alkynes to Construct Trisubstituted Allylic Trifluoromethyl Alkenes
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-01 DOI: 10.1021/acs.orglett.5c00980
Qing-Qing Zhang, Ruo-Xing Jin, Qian Gao, Peng Liu, Ya-Wen Zuo, Quan Lan, Xi-Sheng Wang
{"title":"Regioselective Nickel-Catalyzed Hydrotrifluoroalkylation of Alkynes to Construct Trisubstituted Allylic Trifluoromethyl Alkenes","authors":"Qing-Qing Zhang, Ruo-Xing Jin, Qian Gao, Peng Liu, Ya-Wen Zuo, Quan Lan, Xi-Sheng Wang","doi":"10.1021/acs.orglett.5c00980","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00980","url":null,"abstract":"Introducing fluorine atoms or fluorine-containing groups into drug molecules has become a common approach in drug design, with the incorporation of trifluoromethyl groups as a focal point of research in the field of organic fluorochemistry. Here, we describe a nickel-catalyzed hydrotrifluoromethylation of internal alkynes with trifluoromethyl alkyl bromides to synthesize a series of highly regioselective trifluoromethyl allyl trisubstituted alkenes. This reaction is characterized by mild conditions and broad functional-group tolerance, providing an efficient and practical approach to synthesize trifluoromethyl allyl trisubstituted alkenes.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"22 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745267","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
Divergent Construction of α,α-Difunctionalized Ketones via [1,2]-Sigmatropic Rearrangement/Alkylation-Hydroxylation/Dialkylation of I(III)/S(VI) Ylides
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-01 DOI: 10.1021/acs.orglett.5c00852
Shang-Shi Zhang, Jiaohang Wei, Qiong Hu, Zi-Feng Yang, Wen-Xuan Zou, Dan-Ting Shen, Mei-Zhu Bao, Xiang Liu
{"title":"Divergent Construction of α,α-Difunctionalized Ketones via [1,2]-Sigmatropic Rearrangement/Alkylation-Hydroxylation/Dialkylation of I(III)/S(VI) Ylides","authors":"Shang-Shi Zhang, Jiaohang Wei, Qiong Hu, Zi-Feng Yang, Wen-Xuan Zou, Dan-Ting Shen, Mei-Zhu Bao, Xiang Liu","doi":"10.1021/acs.orglett.5c00852","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00852","url":null,"abstract":"The rare [1,2]-sigmatropic rearrangement of sulfoxonium-iodonium hybrid ylides is described, which enables the efficient sulfoxidation/sulfonylation-alkylation of I<sup>(III)</sup>/S<sup>(VI)</sup> ylides with 1,3-dicarbonyls. By slight modification of the reaction conditions, controllable alkylation-hydroxylation and dialkylation of I<sup>(III)</sup>/S<sup>(VI)</sup> ylides were achieved. This strategy affords a diverse array of α,α-difunctionalized ketones in moderate to good yields, demonstrating broad substrate scope. These findings provide an important advancement in the [1,2]-sigmatropic rearrangement of sulfoxonium ylides and highlight the divergent reactivity of I<sup>(III)</sup>/S<sup>(VI)</sup> ylides.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"20 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143758484","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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