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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
One-Pot Total Synthesis of a Post-translationally Modified Max Transcription Factor Sheds Light on Ser-Phosphorylation and Lys-Acetylation Crosstalk in DNA Binding
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-03-31 DOI: 10.1021/acs.orglett.5c00978
Raj V. Nithun, Shada Khoury, Muhammad Jbara
{"title":"One-Pot Total Synthesis of a Post-translationally Modified Max Transcription Factor Sheds Light on Ser-Phosphorylation and Lys-Acetylation Crosstalk in DNA Binding","authors":"Raj V. Nithun, Shada Khoury, Muhammad Jbara","doi":"10.1021/acs.orglett.5c00978","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00978","url":null,"abstract":"We report a one-pot total synthesis of the transcription factor Max in seven consecutive steps, starting from three peptide segments and employing native chemical ligation. The developed synthesis facilitates the generation of homogeneous Max analogues bearing defined transformations within hours in excellent yields, enabling us to probe the effect of the crosstalk between Ser-phosphorylation and Lys-acetylation on the Max function. Our findings reveal that these post-translational modifications significantly inhibit DNA-binding activity, potentially by disrupting essential Max–DNA interactions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"12 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745269","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
Single-Wavelength Visible-Light-Induced Reversible Isomerization of Stiff-Stilbene under Dynamic Covalent Control
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-03-31 DOI: 10.1021/acs.orglett.5c00707
Indigo M. Bekaert, Maxime A. Siegler, Sander J. Wezenberg
{"title":"Single-Wavelength Visible-Light-Induced Reversible Isomerization of Stiff-Stilbene under Dynamic Covalent Control","authors":"Indigo M. Bekaert, Maxime A. Siegler, Sander J. Wezenberg","doi":"10.1021/acs.orglett.5c00707","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00707","url":null,"abstract":"Formylation of stiff-stilbene enables isomerization by visible instead of UV light, as is monitored by UV–vis and <sup>1</sup>H NMR spectroscopy. Further, it allows dynamic covalent imine formation, which gives rise to slightly blue-shifted absorbance. As a result, the irradiation wavelength that is used to promote <i>E</i> → <i>Z</i> isomerization for the formylated species, causes the opposite <i>Z</i> → <i>E</i> isomerization for the imine derivative. This feature can be used to produce either isomer with the same light source under control of imine formation and hydrolysis. Single crystal X-ray analysis and TD-DFT calculations provide structural and electronic insight.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"40 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143736934","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
Scaffold-Adaptive P450 Enzymes Balance Substrate Promiscuity with Catalytic Specificity in Brassicicene Biosynthesis
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-03-31 DOI: 10.1021/acs.orglett.5c00656
Zhe Chen, Wenling Yuan, Fengli Li, AWei Che, Zhenhua Guan, Zhengxi Hu, Yuan Zhou, Juan V. Alegre-Requena, Junjun Liu, Ying Ye, Yonghui Zhang
{"title":"Scaffold-Adaptive P450 Enzymes Balance Substrate Promiscuity with Catalytic Specificity in Brassicicene Biosynthesis","authors":"Zhe Chen, Wenling Yuan, Fengli Li, AWei Che, Zhenhua Guan, Zhengxi Hu, Yuan Zhou, Juan V. Alegre-Requena, Junjun Liu, Ying Ye, Yonghui Zhang","doi":"10.1021/acs.orglett.5c00656","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00656","url":null,"abstract":"We investigated the functional plasticity of two P450 enzymes, AbnK and AbnG, in the brassicicene biosynthetic pathway. Through <i>in vivo</i> heterologous expression, feeding assays, and <i>in vitro</i> reactions, we show that these enzymes regio- and stereoselectively transform both 5–8–5 and 5–9–5 terpenoid scaffolds in different ways, supported by computational simulations. AbnK also bridges a missing step in brassicicene A biosynthesis. Our findings demonstrate how controlled promiscuity underpins structural diversity, informing strategies to expand chemoenzymatic synthesis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"1 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745246","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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