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Synthesis and Conformational Analysis of α,β‐Dichlorocarbonyl Compounds Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-07-01 Shunta Kobayashi, Nurcahyo Iman Prakoso, Xin Zheng, Shin-ichiro Noro, Masaru Hashimoto, Tatsuya Morozumi, Taiki Umezawa
α,β‐Dichlorocarbonyl compounds were synthesized by facile dichlorination of α,β‐unsaturated amides with TCIA‐PPh3 and the resultant amides were converted to ketones. Conformational analyses of the products were performed to confirm our previous hypothesis regarding vicinal dichlorinated carbonyl compounds. The compounds exhibited 1H NMR signals with large coupling constants (7‐11 Hz) for the 1,2‐anti‐configuration
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Difluorocarbene Enables Modular Synthesis of Difluoroalkylated Bicyclopentanes Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-07-01 Meng-Die Zhang, Hai-Yang Zhao, Xingang Zhang
A straightforward method for the synthesis of difluoroalkylated bicyclopentanes (BCPs) from [1.1.1]propellane (TCP) through a stepwise procedure has been developed. This process involves nucleophilic addition of organozinc or ArMgBr rea‐gents to TCP, followed by reaction with difluorocarbene to generate BCP substituted difluoroalkylzinc species, which subsequently couple with electrophiles, including
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Hydrocyanation of Non‐Activated Alkenes Without Handling HCN Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-07-01 Rafael Chinchilla, Alejandro Baeza
The hydrocyanation of alkenes can be considered a straightforward methodology that gives access to different functionalized organic chemistry entities. This is due to nitrile's high versatility, which can easily undergo further transformations. However, this process has traditionally employed hazardous hydrogen cyanide as the hydrocyanation agent. Therefore, in the last decades, different protocols
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Reduction and Hydrocyanation of Aziridines with C‐C Bond Cleavage Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-29 Yuki Kawamoto, Tomoyuki Yoshimura, Jun-ichi Matsuo
The carbon‐carbon bond in three‐membered ring of 2,3‐diaryl aziridines was reductively cleaved to give the corresponding dibenzylamine derivatives by electrocyclic ring opening of N‐Li or N‐Na aziridines followed by reduction of the 2‐azaallyl anion formed with sodium borohydride in ethanol. Hydrocyanation of the 2‐azaallyl anion with trimethylsilyl cyanide gave a secondary amine bearing a cyano group
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Synthetic Strategies to Prepare Bioactive Lysine and Peptide Conjugates with Triazolium Derivatives Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-29 Patrycja Dominika Ledwoń, Michal Jewginski, Claudia Bello, Francesca Nuti, Paolo Rovero, Rafal Latajka, Anna Maria Papini
Peptides conjugated with organic molecules can be useful tools for the development of novel bioactive compounds. The lysine side‐chain is an interesting functional group to act as a linker to connect small molecules in peptide conjugates. Herein we present the design and synthesis of four Safirinium derivatives, their facile conjugation to lysine in solid phase, and incorporation in peptides. The compounds
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Base‐Promoted Regioselective Synthesis of α‐Amino BODIPYs through Cross‐Dehydrogenative Coupling with Anilines Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-29 Hua Wang, Luying Guo, Huiquan Zuo, Long Wang, Xing Guo, Zhengxin Kang, Zhong-Yuan Li, Lijuan Jiao, Erhong Hao
The construction of C‐N bond at the α‐position of BODIPYs (boron dipyrromethene) not only enables flexible reactivity but also leads to strong electron‐donating properties. In this study, a base‐promoted oxidative cross‐dehydrogenative coupling was developed to synthesize α‐amino BODIPYs with air as a green oxidant. By this strategy, a series of weak nitrogen nucleophiles, such as heteroaryl and aryl
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Reconstructive Approach to the Regiospecific Synthesis of N9‐Alkylated Purines Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-28 Konstantin Valerievich Savateev, Denis A. Gazizov, Pavel A. Slepukhin, Evgeniy N. Ulomsky, Vladimir L. Rusinov
A regiospecific synthesis of N9‐alkylated purines as novel acyclic nucleosides was developed. This approach is based on reconstructive methodology involving the construction of a target heterocyclic scaffold on a readily available 5‐aminotetrazole moiety, which is subsequently cleaved under reductive conditions due to azido‐tetrazole tautomerism. It appeared that the rate of reduction for the azide
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On the Role of the Solvent in the Synthesis of Spirocycles from Alkyne Cations Catalyzed by Triflic Acid: A DFT Study Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-28 Abel de Cózar, Ana Arrieta, Fernando P. Cossío
The role of discrete solvent molecules in the reactivity of alkyne cations has been analyzed computationally. Analysis of the possible reaction mechanisms towards competitive cyclization and elimination processes including a molecule of solvent show the crucial role of dichloromethane (DCM) and tetrahydrofuran (THF). In the presence of DCM, a strong intramolecular p‐cation interaction between the electrophilic
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Organocatalysis for enantioselective decarboxylative nucleophilic addition reactions Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-28 Shuichi Nakamura, Naoki Yasukawa
The catalytic decarboxylation of malonic acid half oxy‐ and thioesters, β‐ketocarboxylic acids, and their related compounds is a straightforward, powerful, and atom‐economical strategy for the in‐situ formation of enolates, which are important and well‐studied synthons for various functional materials and natural products. This strategy, inspired by the biosynthesis of polyketides and fatty acids,
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Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway. Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-28 María Inés Mangione, Darián Vazquez, Rolando Ángel Spanevello, Ariel Marcelo Sarotti
Diels‐Alder between nitroalkenes derived from a sugar scaffold and cyclopentadiene were examined. Depending on chemical structure of nitroalkene and polarity of solvent used, the reaction proceeded via the formation of a nitronate intermediate. Cyclic nitronates highly functionalized were obtained as chemically stable and stereochemically pure compounds. [3,3] sigmatropic shift of these ones afforded
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Redox‐Driven Logic Gates Based on Intramolecular Weak Interactions in Pyridyl‐Containing Diarylnitroxides Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-28 Oleg A. Levitskiy, Igor V. Prolubshikov, Alexey V. Bogdanov, Tatiana V. Magdesieva
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Functionalisation of Chromane by Deprotonative Metallation Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-28 Cléo Bastien, William Erb, Yury S. Halauko, Vadim E. Matulis, Thierry Roisnel, Yann Sarazin, Florence Mongin
Despite the biological interest in chromane derivatives, few studies dedicated to the functionalisation of this heterocycle have been reported. Herein, our objective is to demonstrate the potential of alkali metal bases for the introduction of substituents at its positions 4 and 8, and to explain the observed reactivity based on quantum chemical calculations. Guided by these theoretical results, preliminary
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Chemoselective and Triggered Decomposition of Diazo Esters by the [(IMes)Rh2(OAc)4] Complex: En Route to Assisted Tandem Catalysis from Mixture of Diazo Compounds Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-26 Thomas Lecourt, Jana Hammoud, Vincent Gandon, antoine joosten
Decomposition of aryl and unsubstituted diazo ester into Rh(II)‐carbenes by the [(IMes)Rh2(OAc)4] complex is shown to be slower than with Rh2(OAc)4. Diazo esters substituted by a second electron‐withdrawing group do not suffer nitrogen extrusion when exposed for several hours to this Rh(II)·NHC complex at room temperature. This chemoselective decomposition of diazo esters depending on their substituent
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Post‐functionalization of Organoboranes by Cu‐Catalyzed Azide Alkyne [3+2]‐Cycloaddition Reaction Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-26 Mélanie Bonnard, Sandra Pinet, Laurent Chabaud, Mathieu Pucheault
The copper‐catalyzed azide alkyne [3+2]‐cycloaddition (CuAAC) reaction of organoboranes represents an attractive area of research within the field of click chemistry, with diverse applications in organic synthesis, medicinal chemistry, or materials science. Despite the potential issues caused by the copper insertion into the carbon‐boron bond, significant progress has been made to harness the reactivity
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Front Cover: Green Light‐Responsive D‐π‐A‐π‐D Quinoxaline Emitters for Luminescent Solar Concentrators: Potential Integration in Agrivoltaic Systems (Eur. J. Org. Chem. 24/2024) Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-26 Giulio Goti, Gianna Reginato, Carmen Coppola, Alessio Dessì, Daniele Franchi, Alessandro Mordini, Alberto Picchi, Andrea Pucci, Adalgisa Sinicropi, Lorenzo Zani, Massimo Calamante
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Effect of Solvate Ionic Liquids in the Enantioselective (S)‐Proline‐Catalyzed Mechanochemical Robinson Annulation. Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-25 Ismael J. Arroyo-Córdoba, Gonzalo Gamboa-Velázquez, Claudia Gabriela Ávila-Ortiz, Carlos Naranjo-Castañeda, Eusebio Juaristi
Herein we report our observations from the study of the classical Robinson annulation reaction under solvent‐free mechanochemical activation by means of high‐speed ball milling. In particular, the enantioselective synthesis of the Wieland‐Miescher ketone was used as model reaction. (S)‐Proline was employed as chiral organocatalyst, either alone or in the presence of additives in order to determine
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Experiment Meets Theory: Cope Rearrangements and Thermal E/Z Isomerisations of Terpenoid Hydrocarbons Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-25 Kizerbo Taizoumbe, Anuj Chhalodia, Bernd Goldfuss, Jeroen S. Dickschat
Several terpenes are known that can undergo a Cope rearrangement. Prominent examples include germacrene A and hedycaryol that show a Cope rearrangement already slightly above room temperature. In the present study the Cope rearrangements of several terpenes and eventually co‐occurring thermal E/Z isomerisations were investigated experimentally for their minimum required temperatures and for their states
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Cover Feature: One-Pot Gold/Acid-Catalyzed Synthesis of Indolo[1,2-a]quinolin-5(6H)-ones from 1-(2-Ethynylphenyl)-1H-indoles (Eur. J. Org. Chem. 23/2024) Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-19 Elisa Brambilla, Mariaclara Gugiatti, Silvia Rizzato, Giorgio Abbiati, Valentina Pirovano
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Mild C‐H Alkoxylation of Aromatic Amides Catalyzed by Salicylaldehyde‐Co(II) Complexes Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-22 Xiao-Hong Chen, Yi-Qing Xu, Mao-Gui Huang, Yu-Yan Tan, Yu-Han Li, Jia-Wei Li, Yue-Jin Liu
A simple and efficient salicylaldehyde‐promoted cobalt‐catalyzed protocol for the C‐H alkoxylation of aromatic amides by employing primary alcohols as the coupling partner has been developed. This method utilizes a 8‐aminoquinoline moiety as the directing group and successfully achieves the ortho‐C‐H alkoxylation in moderate to good yields under mild conditions. This protocol features excellent functional
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Transition‐Metal‐Free Perfluoroalkylation of N‐Thiophthalimides or N‐Thioimides to Access Perfluoroalkyl Sulfides Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-21 Wenting Liu, Han Qian, Zijie Song, Yong Liu, Jiajian Peng, Wen-Wu Sun, xinxin shao, Ying Bai
A practical and efficient trifluoromethylation of readily available and bench stable N‐Thiophthalimides and N‐Thioimides with Ruppert‐Prakash reagent (TMS‐CF3) is described. The reaction proceeds at room temperature and only requires NaOAc as the mild promoter to prepare a series of trifluoromethyl thioethers in good to excellent yields. Both aryl and alkyl derivates are well trifluoromethylated under
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Trifluoromethylsulfinyl Compounds: Recent Synthetic Approaches and Future Perspectives Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-21 Fangcan Liang, Dianhu Zhu
The introduction of trifluoromethylsulfinyl group into the required target molecules has become an indispensable strategy for pharmaceutical chemists to improve the success of new drug discovery. Compared with the indirect methods, direct trifluoromethylsulfinylation by employing available trifluoromethylsulfinylating reagents is an important and elegant strategy for the rapid assembly of valuable
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Metal‐Free Visible‐Light‐Induced Hydrodifluoroalkylation of Electron‐Deficient Alkenes Using Hantzsch Ester Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-21 Juan Wang, Ke Ren, Jian Hao, Wen Wan
A mild, metal‐free Giese‐type hydrodifluoroalkylation of electron‐deficient alkenes under visible‐light irratiation has been developed. This highly reducing photoactivated Hantzsch ester facilitates C(sp3)‐CF2 bond formation through photoinduced electron transfer (PET) and hydrogen atom transfer (HAT) processes, providing an easy access to diverse gem‐difluorinated alkanes.
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Controlled Reactivity of Viologens in Alkaline Solutions Via Cucurbit[7]uril Complexation Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-21 Axel Bossavit, valerie monnier, Didier Siri, Gabriel Canard, Didier Gigmes, David Bardelang, Anthony Kermagoret
A series of N‐alkyl‐ and N‐aryl‐viologens has been studied in alkaline solutions. In this work, we evaluated the deuteration rate of the viologens in D2O solutions of pH values ranging from 7.3 to 12.7. Kinetic experiments and computational calculations showed the high reactivity of H‐C(2) bonds toward deprotonation of N‐aryl‐pyridinium moieties compared to N‐alkyl‐pyridinium moieties, even in hybrid
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Synthesis of Lactones via Electrochemical Sequential Oxidative Process Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-21 Ming Fang, Peinan Shang, Hai Huang, Jianwei Sun, Zhengyu Han
Herein, we unveil a novel electrochemical oxidative strategy that facilitates the synthesis of lactones from 2‐arylbenzaldehydes and 2‐arylbenzoic acids. Crucially, our method allows for the convergent synthesis of lactones from the combinations of the respective 2‐arylbenzaldehyde and 2‐arylbenzoic acid as starting material, owing to the oxidative process's compatibility within our electrochemical
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Front Cover: Benzocoumarin-Fused Triskelions Exhibit AIEE Due to Inhibited Molecular Inversion (Eur. J. Org. Chem. 23/2024) Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-19 Masafumi Ueda, Midori Kuramochi, Riho Shimizu, Yuki Ohba, Norifumi Yamamoto, Yasuhiro Mazaki
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Rh‐Catalyzed [4+3] Annulation of N‐Sulfonyl‐1,2,3‐Triazoles with 4‐Vinyl Indoles to Access Azepinoindoles Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-20 Ze-Hua Wang, Ze-Feng Xu, Jing Feng, Mingming Yu
The present study provided an efficient synthesis pathway to the azepino[5,4,3‐cd]indoles using N‐sulfonyl‐1,2,3‐triazoles and 4‐vinylindoles through a cascade carbene insertion and intramolecular aza‐Michael addition. This method is distinguished by mild reaction conditions, straightforward operational steps, accessible starting materials, and broad substrate compatibility. Furthermore, the versatility
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Electro‐Organic Stereoselective Dehydrogenative Homo‐Coupling of β‐Naphthylamines Derivatives Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-20 Maurizio Benaglia, Simonetta Resta, Fabrizio Medici, Stefano Andolina, Sergio Rossi
the electrochemical stereoselective dehydrogenative homocoupling of b‐naphthylamine derivatives was investigated and successfully accomplished, the chiral diaryl amines being obtained in up to 60% yield. The use of an enantiopure b‐naphthylamine featuring an aminoalcohol as chiral auxiliary led to the expected 2,2’‐binaphthyl diamine derivative in up to 96/4 diastereoisomeric ratio. The application
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Corrigendum: Photoinduced Single‐Electron Reduction of Alkenes Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-20
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Reaction Course Dependent Regiospecific Transformation of 4-Azido-Coumarin into Coumarin C3-C4 Fused Imidazole and 5-Substituted-1,4-Benzodiazepine Scaffolds Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-18 Sriraghavan Kamaraj, Vediyappan Nagamani
Herein, we report an efficient route for coumarin C3-C4 fused imidazole scaffolds via indium chloride-mediated single-step transformation of 4-azido-coumarin with amines/aldehydes and coumarin C3-C4 fused 5-substituted-1,4-benzodiazepine scaffolds with 1,2-azide-nitrogen migration through two-step sequential synthesis via the transitory intermediacy of 2,3-bridged-2H-azirine. A plausible mechanistic
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Palladium-Catalyzed Direct Alkynylation of Carbazoles with Alkynyl Bromides Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-18 Jyothis Dharaniyedath, Vikash Kumar, Parthasarathy Gandeepan
Carbazole derivatives are vital in medicinal and materials chemistry, yet accessing diverse substitutions remains challenging. Here, we introduce a regioselective approach for C1 and C8 alkynylation of carbazoles via palladium-catalyzed C‒H activation. This method provides a direct route to mono- and di-alkynylated derivatives, addressing the scarcity of alkynylated carbazole-based materials. Our study
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Magnetically Reusable Fe3O4-CuO Nanoparticles as Catalysts for the Synthesis of Aryl-Substituted Fluorescent Pyrazines for Fe Sensing and Ink Applications Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-18 Dibya Das, Tanmayee Mohanta, Ashis Kumar Jena
Abstract. Synthesis of substituted pyrazines from readily available methyl aryl/heteroaryl ketones and 1,2-diamines were achieved using highly stable and reusable ferrite stabilized copper nanoparticles (Fe3O4-CuO) as catalyst. The reaction proceeds via cascade imine formation-oxidative cyclization method under oxygen atmosphere. The nanocatalysts were easily recovered and reused upto three consecutive
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HFIP-Promoted Short Total Synthesis of Gochnatiolide D and Ainsliadimer A from Dehydrozaluzanin C Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-18 Antonis Kelesidis, Kyriaki Gennaiou, Alexandros L. Zografos
The total syntheses of gochnatiolide D and ainsliadimer A were achieved through a streamlined one-pot sequence starting from their biogenetic precursor dehydrozaluzanin C. These biomimetic, protecting group-free syntheses involve the elegant orchestration of the highly diastereoselective hetero-Diels-Alder reaction of dehydrozaluzanin C, its subsequent hydrolysis to gochnatiolide D and finally an aldol
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Unraveling the Potential of Cyclic N-Sulfonyl Ketimines in the MCR Universe Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-18 Constantinos Neochoritis, Michael Fragkiadakis, Eirini Fotopoulou, Konstantinos Froudas
Cyclic N-sulfonyl ketimines constitute an accessible class of lead-like heterocycles with a vast application in both synthetic organic and medicinal chemistry. In this context, we harness the capabilities of these heterocycles in four different isocyanide-based multicomponent reactions. Our goal was to create libraries of compounds with functional groups and vectors that are compatible for structural
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In DFT We Trust: Exhaustive Exploration of 1,3-Dipolar Cycloadditions Between Nitrones and Levoglucosenone Exposes a Curious Case of Conformational Dynamics Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-18 Soledad Cicetti, Ariel Sarotti, Rolando A. Spanevello
An experimental and computational study (including DFT calculations and distortion/interaction analysis) was conducted to assess the effect of the nitrone structure in the outcome of dipolar 1,3-cycloadditions with levoglucosenone, a biomass derived chiral enone. While B3LYP/6-31G* (the most popular method for modeling these reactions according to our literature search) provides qualitatively good
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Iron(ΙΙΙ) Catalyzed Aerobic Cα–Cβ Cleavage of Allylic Alcohols Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-18 Christos I. Stathakis, Georgia G. Bagkavou
The regiospecific Cα–Cβ cleavage of allylic alcohols under modified aerobic Mukaiyama hydration conditions is presented. The new methodology can be regarded as an equivalent of a two-step process, a typical hydration of the parent allylic alcohol followed by a 1,2-diol cleavage. A broad scope of substrates, both cyclic and acyclic, are applicable, thus introducing substantial structural modification
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Accessing Polysubstituted NH Pyrroles from Nitroalkenes via [4+2]-Cycloaddition/Reductive Ring Contraction Strategy Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-17 Evgeny Pospelov, Alexander Zhirov, Baglan Kamidolla, Alexey Sukhorukov
A novel two-step access to polysubstituted pyrroles from nitroalkenes was developed. It involves [4+2]-cycloaddition with enol ethers to give six-membered cyclic nitronates followed by reductive ring contraction with Ra-Ni/AcOH or Ra-Ni/EtOH systems. The process is applicable to a variety of nitroalkenes and enol ethers bearing electron-rich and electron-poor substituents and functional groups. The
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Organocatalytic Diastereo- and Enantioselective Michael Addition of α‑Aryl Isocyanoacetates to Aurone-Derived Azadienes Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-17 Adrián Laviós, Amparo Sanz-Marco, Carlos Vila, Gonzalo Blay
A highly diastereo- and enantioselective organocatalytic Michael addition of α-aryl isocyanoacetates to aurone-derived azadienes under mild conditions has been developed. This efficient methodology enables access to chiral α,α-disubstituted α-amino ester derivatives with two adjacent stereocenters, one of them quaternary, bearing a benzofuran scaffold in their structure in high yields and stereocontrol
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Organocatalytic Activation of Unsymmetrical 2,3-Diketones towards Catalytic Asymmetric Domino Michael–Henry Reaction Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-17 Łukasz Włoszczak, Marcin Górecki, Jacek Mlynarski
In this study, we explored a method to distinguish between both enolizable regions of unsymmetrical 2,3-diketones in organocatalytic domino reactions involving nitroalkenes. The selective formation of an enamine from only one side of the molecule was made possible by the use of optically pure 2-(trifluoromethyl)pyrrolidine. This catalyst, remarkably enhancing the reaction, owes its efficacy to a unique
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Synthesis of (E)-Enaminoesters by a 1,6-Addition/Fragmentation Cascade Involving Coumalic Acid Esters and Secondary Amines Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-17 Tania Xavier, Sylvie Condon, Christophe Pichon, Erwan Le Gall, Marc Presset
Coumalic acid methyl ester (methyl coumalate), a biomass-derived building block, was converted into (E)-enaminoesters by an original uncatalyzed stereoselective 1,6-addition/fragmentation cascade involving secondary amines. The transformation occurred under useful experimental conditions as a simple heating of a stoichiometric mixture of the starting compounds led to the desired products. The reaction
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Synthesis of Deoxy Pyranosides via Fe(III) Catalyzed Regioselective Thiocarbonylation of Partially Protected Carbohydrates Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-16 Jie Zhao, Xiaorui Zhang, Qichang Yang, Haifeng Wang, Shuang-Xi Gu, Qiongjiao Yan, Jian Lv, Fen-Er Chen
Rapid and efficient synthesis of targeted deoxygenated glycosides is highly desired. Herein, we disclose a two-step procedure for the synthesis of deoxysugars from partially protected pyranosides via site-selective thiocarbonylation followed by tin-free Barton–McCombie deoxygenation. The selectivity can be smoothly achieved through FeCl3 as the catalyst assisted by low-priced benzoyl trifluoroacetonate
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Enantioselective Synthesis of Antifungal Agent Voriconazole via Asymmetric Epoxidation of Tetrasubstituted (Z)-Alkene Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-14 Jiale Peng, Ran Li, Zhuo Li, Yu Tang, Jin-Song Yang, Fei Xue, Yong Qin
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Organometallic-Free Approaches to the Direct Arylation of Benzoquinones and Naphthoquinones Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-14 Daniela Martins, Nayane Abreu do Amaral e Silva, Noemi de Jesus Hiller, Fernando de Carvalho da Silva, Vitor Francisco Ferreira
Quinones represent a ubiquitous class of natural products, extensively distributed throughout nature. Within these organisms, they fulfil pivotal roles across a spectrum of metabolic processes essential to the organisms. Their privileged core structure is present in a variety of substances explored in medicinal chemistry. Modification of the central core of quinones could give rise to new substances
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Understanding the Role of Internal Lewis Acids in the Catalytic Activity of Urea-Based Hydrogen Donors Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-13 Susana Portela, Israel Fernandez
Detailed quantum-chemical calculations have been carried out to understand both the origin of the catalysis in the urea-catalyzed nucleophilic ring-opening of nitrocyclopropanes and the acceleration induced by the presence of an internal Lewis acid in the catalyst. To this end, the mode of activation of these ureas is quantitatively analyzed in detail by means of the Activation Strain Model of reactivity
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Sc(OTf)3-Catalyzed Synthesis of 3-Substitued Lawsones through a Buchner–Curtius–Schlotterbeck Reaction Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-11 Dr Sailam Sri Gogula, Dasari Vijaya Prasanna, B Sridhar, Ch. Abraham Lincoln, P Muralidhar Reddy, B V Subba Reddy
An efficient strategy has been developed for the synthesis of 3-substituted lawsones using a catalytic amount of Sc(OTf)3 in toluene at -78 °C through a Buchner-Curtius-Schlotterbeck reaction. It is a versatile method to produce a large number of 3-aryl, 3-styryl, 3-alkyl, and 3-heteroaryl substituted lawsones under mild conditions. This is a first report on the synthesis of 3-substituted lawsones
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(Radio)Fluorination Reactions for the Synthesis of Aryl Fluorides: Recent Advances and Perspectives Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-11 Jie Han, Zhanming Zhang
The formation of carbon-fluorine (C-F) bonds is an important research field in organic synthesis because the insertion of a fluorine atom into an organic compound can alter its physicochemical properties, such as metabolic stability and permeability. Due to this unique property, organic fluorinated compounds, especially aryl fluorides, have a wide range of applications in various fields, including
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Streamlined Electrochemical Dihalogenation (F, Cl, and Br) of gem-Difluoroalkenes Using Hydrogen Halides as Reagents Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-10 Xiaoying Wang, Rui Zhang, Jiaxi Cai, Xin Liu, Haixia Song, Le Liu, Xin-Hua Duan, Mingyou Hu
We established a straightforward electrochemical dihalogenation (F, Cl, and Br) process for gem-difluoroalkenes. This reaction exhibits a broad functional group tolerance and has been effectively utilized in the construction of complex molecules. The subsequent synthetic transformations of the products have highlighted the adaptable nature of the dihalogenated compounds, demonstrating their potential
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Front Cover: Cyclodextrin-Based Catenanes Platformed with meso-Arylporphyrin (Eur. J. Org. Chem. 22/2024) Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-11 Kaoru Asai, Qiyue Mao, Atsuki Nakagami, Hiroaki Kitagishi
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Cover Feature: A Perspective on Centrohexaindane Chemistry and a Deep-Sleeping “Cartesian” Seed (Eur. J. Org. Chem. 22/2024) Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-11 Dietmar Kuck
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Detection and Differentiation of Amines and N-Heterocycles via Recognition Enabled Chromatographic 19F NMR Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-10 Guangxing Gu, Yilin Zeng, Tianci Peng, Wenjing Bao, Ziyang Zhang, Jian Wu, Yanchuan Zhao
In this study, we successfully employed a 19F-labeled cyclopalladium probe to achieve simultaneous differentiation and detection of various amines and N-heterocyclic compounds. This method features a broad detection window, facilitating the discrimination and multi-component analysis of structural analogs and isomers through the generation of characteristic 19F NMR signals with distinct chemical shifts
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Mixed Liquid and Solid Phase Synthesis of Isopeptidic Desferrioxamine Analogues for Complexation of Zirconium Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-10 Lasse Outzen, Hoang Duc Nguyen, Darius Ludolfs, Wolfgang Maison
89Zr has a number of advantageous properties for PET-imaging, but optimal chelators for its widespread clinical application still need to be found. Tetrahydroxamates derived from the natural siderophore DFOB are promising candidates in this context. This study describes a solid-phase approach to isopeptide analogs of DFOB (termed ipDFO*) with four hydroxamate groups for stable Zr(IV)-chelation. The
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Enantioselective Synthesis of Axially Chiral Heterobiaryl N-Cbz-Protected Diamines via Organocatalytic Arylation of 5-Aminoisoxazoles Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-08 Qian Li, Yuan-Yuan Xu, Tao Wang, You-Qing Wang
An enantioselective arylation of isoxazoles with N-Cbz-protected azonaphthalenes is disclosed, affording a range of axially chiral arylisoxazoles in good yields and excellent enantiocontrol by utilizing chiral phosphoric acid. Cbz protecting group can be readily removed, resulting in five-six membered axially chiral heterobiaryl amines bearing free amine maintaining enantiomeric purity.
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Front Cover: Kinetic Resolution of Cyclic Tertiary Alcohols with Lipase A from Candida Antarctica (Eur. J. Org. Chem. 21/2024) Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-07 Satoshi Horino, Karla Wagner, Anke Hummel, Kyohei Kanomata, Harald Gröger, Shuji Akai
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Palladium-Catalyzed Direct C(sp3)−H Arylation of 5H-Imidazo[2,1-a]isoindole Scaffolds With Arylbromides Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-10 Florian Panza, Alexandre Hauwelle, Antoine Briquet, Ali Awada, Vincent Levacher, Christophe Hoarau, Christine Baudequin
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Factors Governing Chemoselectivity in Alkanolamines: A Panoramic Overview Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-07 Jigyansa Sahoo, Jeetendra Panda, Sukanya Mandal, Gokarneswar Sahoo
The most challenging aspect of chemical synthesis has always been attainment of high chemoselectivity levels. This review will provide a panoramic view on how the innate reactivity of two nearly reactive functional groups (-O/-N) can be controlled or reversed for the chemoselective functionalisation in alkanolamines. A comprehensive compilation of reports encasing various methodologies developed to
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Synthesis of Fluorine-containing C2-Tetrasubstituted Indolin-3-ones via Rapid Incorporation of Difluoroacetate Radical into 2-Aryl-3H-indol-3-ones Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-07 Qian Li, Shi-Na Zhao, Ganpeng Li, Yonghui He, Xiao-Jing Zhao
Here, we have successfully achieved the addition of difluoroacetate radicals to 2-aryl-3H-indol-3-ones, enabling various difluoroalkylations of C2-tetrasubstituted 2-aryl indolin-3-ones in a highly efficient and economical manner. It is worth mentioning that these difluoroalkylation compounds can be easily transformed into various derivatives under mild reaction conditions. Control experiments suggest
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Stereoselective Synthesis of Key Skeleton of Mohangic Acids A-E Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-06 Joyanta Mondal, Sandip Guchhait, Himangshu Sharma, Rajib Kumar Goswami
The key skeleton that could allow to access structurally intriguing mohangic acids A-E has been synthesized in stereoselective manner. The salient features of this synthesis include Evans syn-aldol reaction to construct the C-11 and C-12 centers, HWE olefination to construct C14-C15 bond, Evans asymmetric methylation to install C-14 center and Crimmins acetate aldol to generate C-15 center whereas
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Binding of Linear Anions and Formation of Anion Encapsulated Dimeric Capsular Assembly by Cis-5,15-bis(3,5-trifluorometylphenyl)calix[4]pyrrole Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-06 Ashoke Kumar Patra, Anik Roy, Rosa M Gomila, Somenath Kundu, Soumya Srimayee, Dibakar Halder, Rajat Saha, Chang-Hee Lee, Maidul Hossain, Antonio Frontera, Debasis Manna, Indrajit Saha
Cis-5,15-bis(3,5-trifluorometylphenyl)calix[4]pyrrole (1) forms stable 1/1 complexes with linear anions such as N3-, SCN‑ and NCO‑ with the highest affinity for NCO- anion in acetonitrile solution. Crystallization of receptor 1 with TBASCN and (TMA)2SO4 resulted in the formation of dimeric capsular assembly, {(TMA)2[12•(SCN)2]}, in which two thiocyanate anions are encapsulated. On the other hand, 1•OCN(TMA)
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Asymmetric Rh Diene Catalysis under Confinement: Isoxazole Ring-Contraction in Mesoporous Solids Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-06 Max Marshall, Zarifishan Dilruba, Ann-Katrin Beurer, Kira Bieck, Sebastian Emmerling, Felix Markus, Charlotte Vogler, Felix Ziegler, Marina Fuhrer, Sherri S. Y. Liu, Shravan R. Kousik, Wolfgang Frey, Yvonne Traa, Johanna R. Bruckner, Bernd Plietker, Michael R. Buchmeiser, Sabine Ludwigs, Stefan Naumann, Petia Atanasova, Bettina V. Lotsch, Anna Zens, Sabine Laschat
Covalent immobilization of chiral dienes in mesoporous solids for asymmetric heterogeneous catalysis is highly attractive. In order to study confinement effects in bimolecular vs monomolecular reactions, a series of pseudo-C2-symmetrical tetrahydropentalenes was synthesized and immobilized via click reaction on different mesoporous solids (silica, carbon, covalent organic frameworks) and compared with
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UNDERSTANDING GOLD-ALKYNE ACTIVATION FROM BOND DISSOCIATION ENERGIES OF GOLD-ALKYNE COMPLEXES Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-06 David Gatineau, Denis Lesage, Rodolphe Gueret, Samuel Danladi Mador, Anne Milet, Yves Gimbert
A detailed approach into electronic effects of ligands on gold-alkyne interactions has been carried out in the gas phase using tandem mass spectrometry. A semi-empirical method coupled to DFT calculations was used to quantify ligands effects on Au-CC bond strength. To this end, the critical energies of 16 [L-Au-hex-3-yne]+ complexes with different L ligands were determined through collision induced
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Preparation and Aldol Couplings of 3(2H)-Furanones: Stereoselective Synthesis of the C8-C22 Fragment of Tuscoron A Eur. J. Org. Chem. (IF 2.5) Pub Date : 2024-06-06 Michelle Fernandez Bieber, Xin Gao, Raphael Wagner, Björn Holzapfel, Pascal Tomczyk, Dirk Menche
Various strategies for synthesis and stereroselective aldol coupling of furan-3(2H)-ones were evaluated that eventually enabled a highly stereroselective synthesis of the C8-C22 fragment of tuscoron A.