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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
Asymmetric Synthesis of the Tetracyclic Core of Venezuelaene B
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-01 DOI: 10.1021/acs.orglett.5c00301
Louxi Chen, Chao-Han Zhang, Junyang Liu, Jianwei Sun, Chuang-Chuang Li
{"title":"Asymmetric Synthesis of the Tetracyclic Core of Venezuelaene B","authors":"Louxi Chen, Chao-Han Zhang, Junyang Liu, Jianwei Sun, Chuang-Chuang Li","doi":"10.1021/acs.orglett.5c00301","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00301","url":null,"abstract":"A concise and efficient approach for the asymmetric synthesis of the tetracyclic core of venezuelaene B is described. Its uncommon and synthetically challenging [5–5–6–7] tetracyclic skeleton was constructed via a mild acid-promoted type I [5+2] cycloaddition, followed by a diastereoselective intramolecular Pauson–Khand reaction. The described chemistry establishes the feasibility of constructing the [5–5–6–7] tetracyclic core and several desired stereocenters (C2, C10, C11, and C14) of the final product.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"69 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143758665","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 通过 I(III)/S(VI) Ylides 的 [1,2]-Sigmatropic Reearrangement/Akylation-Hydroxylation/Dialkylation 异构α,α-二官能化酮
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
Synthesis of 4-Nitroisoxazole-Based Energetic Materials
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-01 DOI: 10.1021/acs.orglett.5c01074
Alexey A. Konnov, Anton D. Lisyutkin, Dmitry B. Vinogradov, Amina A. Nazarova, Alla N. Pivkina, Leonid L. Fershtat
{"title":"Synthesis of 4-Nitroisoxazole-Based Energetic Materials","authors":"Alexey A. Konnov, Anton D. Lisyutkin, Dmitry B. Vinogradov, Amina A. Nazarova, Alla N. Pivkina, Leonid L. Fershtat","doi":"10.1021/acs.orglett.5c01074","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01074","url":null,"abstract":"A set of novel biheterocyclic energetic materials incorporating the 4-nitroisoxazole scaffold was synthesized. Thus, prepared species demonstrated excellent thermal stability (181–244 °C), good densities (1.71–1.74 g·cm<sup>–3</sup>), and detonation velocities (7.6–8.3 km s<sup>–1</sup>), while retaining insensitivity to friction. To the best of our knowledge, this is the first example of an incorporation of the 4-nitroisoxazole scaffold into the structure of high-energy materials.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"134 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745268","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
Correction to “Ring Opening of Aziridines by Pendant Silanols Allows for Preparations of (±)-Clavaminol H, (±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and (±)-N-Hexanoyldihydrosphingosine” 对 "通过硅烷偶联醇打开氮丙啶环，制备出(±)-克拉维诺 H、(±)-去乙酰基克拉维诺 H、(±)-二氢鞘磷脂和(±)-N-己酰基二氢鞘磷脂 "的更正
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-01 DOI: 10.1021/acs.orglett.5c01213
Someshwar Nagamalla, Debobrata Paul, Joel T. Mague, Shyam Sathyamoorthi
{"title":"Correction to “Ring Opening of Aziridines by Pendant Silanols Allows for Preparations of (±)-Clavaminol H, (±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and (±)-N-Hexanoyldihydrosphingosine”","authors":"Someshwar Nagamalla, Debobrata Paul, Joel T. Mague, Shyam Sathyamoorthi","doi":"10.1021/acs.orglett.5c01213","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01213","url":null,"abstract":"We have corrected the synthetic procedures for N–H aziridines in the Supporting Information. In the original version, Rh<sub>2</sub>(esp)<sub>2</sub> was accidentally omitted from the synthetic procedures. The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.5c01213. Experimental procedures, reasoning for structural assignments, NMR spectra, and crystallographic information (PDF) Correction to\u0000“Ring Opening of Aziridines by\u0000Pendant Silanols Allows for Preparations of (±)-Clavaminol H,\u0000(±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and\u0000(±)-N-Hexanoyldihydrosphingosine” <span> 0 </span><span> views </span> <span> 0 </span><span> shares </span> <span> 0 </span><span> downloads </span> Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html. This article has not yet been cited by other publications.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"721 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143758490","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
Fe(III)-Catalyzed Stereoselective Synthesis of α-Alkenyl-γ-lactams via Radical Cyclization of 1,6-Enyne-Type Ugi 4-CR Adducts
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-03-31 DOI: 10.1021/acs.orglett.5c00544
Silvia J. Becerra-Anaya, Luis A. Polindara-García
{"title":"Fe(III)-Catalyzed Stereoselective Synthesis of α-Alkenyl-γ-lactams via Radical Cyclization of 1,6-Enyne-Type Ugi 4-CR Adducts","authors":"Silvia J. Becerra-Anaya, Luis A. Polindara-García","doi":"10.1021/acs.orglett.5c00544","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00544","url":null,"abstract":"A novel and highly stereoselective synthesis of α-alkenyl-γ-lactams via an Fe(III)-catalyzed radical 5-exo-<i>dig</i> cyclization of 1,6-enyne-type Ugi 4-CR adducts is described. This method operates under mild conditions and requires short reaction times, enabling the efficient construction of these valuable scaffolds while demonstrating broad substrate compatibility and good yields.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"15 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143736835","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
Photoinduced Copper-Catalyzed Radical Mizoroki–Heck Reaction with Unactivated Alkyl Iodide
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-03-31 DOI: 10.1021/acs.orglett.5c00602
Yongjie Xu, Hang Luo, Dan Hu, Lei Gao, Fangnian Yu, Sijia Li, Chen-Yi Li, Yu-Long Li, Min Gao, Luqing Lin
{"title":"Photoinduced Copper-Catalyzed Radical Mizoroki–Heck Reaction with Unactivated Alkyl Iodide","authors":"Yongjie Xu, Hang Luo, Dan Hu, Lei Gao, Fangnian Yu, Sijia Li, Chen-Yi Li, Yu-Long Li, Min Gao, Luqing Lin","doi":"10.1021/acs.orglett.5c00602","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00602","url":null,"abstract":"Herein, we present a method for copper-catalyzed photoinduced radical Mizoroki–Heck (M-H) reactions utilizing unactivated alkyl iodides and styrene. This approach enables the smooth generation of (<i>E</i>)-olefin products with a good functional group tolerance, demonstrating broad applicability. The mechanism involves the in situ formation of a copper complex that binds to the alkyl iodide, leading to radical fragmentation under visible-light irradiation. This process generates alkyl radicals and a persistent copper(II) radical complex, both of which are crucial for subsequent olefin formation. Primary mechanistic studies support the photoinduced cleavage of the C(sp<sup>3</sup>)–I bond via an inner-sphere electron transfer (ISET) process involving an excited Cu(I) complex associated with the alkyl iodide. Finally, the formation of the M-H product occurs via a base-assisted β-H elimination process.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"36 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143736836","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
One-Pot Sequential Alcohol Activation and Nickel-Catalyzed Cross-Electrophile Coupling with Chlorosilanes
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-03-31 DOI: 10.1021/acs.orglett.5c00830
Xiaojie Liu, Biping Xu, Martin Oestreich
{"title":"One-Pot Sequential Alcohol Activation and Nickel-Catalyzed Cross-Electrophile Coupling with Chlorosilanes","authors":"Xiaojie Liu, Biping Xu, Martin Oestreich","doi":"10.1021/acs.orglett.5c00830","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00830","url":null,"abstract":"A formal deoxygenative silylation of primary alcohols is reported. The one-pot procedure consists of an <i>in situ</i> bromination of the alcohol and a subsequent nickel-catalyzed cross-electrophile coupling of the formed alkyl bromide and various vinyl-substituted chlorosilanes. The key to success is the compatibility of the nickel catalysis as well as the chlorosilane electrophile with the byproducts of the preceding bromination step, especially with triphenylphosphine oxide likely acting as a weak ligand for the excess nickel catalyst used.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"88 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143736936","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
Driving Feringa Motors with Visible Light by Intermolecular Singlet Energy Transfer from a Commercial [Ru(bpy)3]2+ Photosensitizer
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-03-31 DOI: 10.1021/acs.orglett.5c00490
Cheng Luo, Guohong Liao, Ziwei Jiang, Chen Zhang, Bin Liu, Li Liu, Yanling Luo, Quan Li
{"title":"Driving Feringa Motors with Visible Light by Intermolecular Singlet Energy Transfer from a Commercial [Ru(bpy)3]2+ Photosensitizer","authors":"Cheng Luo, Guohong Liao, Ziwei Jiang, Chen Zhang, Bin Liu, Li Liu, Yanling Luo, Quan Li","doi":"10.1021/acs.orglett.5c00490","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00490","url":null,"abstract":"We herein report that a commercialized photosensitizer, Ru(bpy)<sub>3</sub>Cl<sub>2</sub>, can be successfully employed to “uphill” drive the rotation of Feringa motors via a singlet rather than an intuitive triplet intermolecular energy transfer mechanism, offering new insights into the sensitization strategy to power Feringa motors with more biocompatible light sources.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"58 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143737112","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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