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Green Light-Responsive D-π-A-π-D Quinoxaline Emitters for Luminescent Solar Concentrators: Potential Integration in Agrivoltaic Systems Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-18 Giulio Goti, Gianna Reginato, Carmen Coppola, Alessio Dessì, Daniele Franchi, Alessandro Mordini, Alberto Picchi, Andrea Pucci, Adalgisa Sinicropi, Lorenzo Zani, Massimo Calamante
the integration of photovoltaic technologies within agricultural settings, also known as agrivoltaic, is attracting increasing attention as a sustainable approach to ensure both clean energy and food supply. The success of this strategy relies on the development of innovative materials that can selectively convert specific wavelengths into energy while being transparent to photosynthetically relevant
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Tf2O-Promoted Synthesis of Ureas, Carbamates and Thiocarbamate via Lossen Rearrangement: A Mechanistic Insight Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-17 Eti Chetankumar, Chinthaginjala Srinivasulu, Ganga Periyasamy, Vommina Venkata Sureshbabu
Herein, we report triflic anhydride mediated synthesis of ureas starting from hydroxamic acids. The scope of triflic anhydride was also expanded to encompass carbamates. In addition, this reaction is applicable to activation of hydroxamic acid derivative of dipeptide giving α-uriedopeptidomimetics in good yield. The mechanistic study of reaction was carried out by DFT. This study is important because
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A Simple Device for Automated Mixing of Heterogeneous Solid-Liquid Reactions During In-Situ Monitoring by NMR Spectroscopy Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-17 Yuan Gao, Andrew M. R. Hall, Nicole A. Fohn, Edward J. King, Lloyd A. L. Mitchell, George A. Steedman, Guy Charles Lloyd-Jones
In-situ NMR spectroscopy can provide valuable insight into chemical reactions, including detailed information on reaction kinetics and thus mechanism. The application of in-situ NMR techniques to heterogeneous reactions has so far been limited by the requirement for efficient mixing, which is challenging within the confines of a standard NMR spectrometer. We report an automated plunger-based device
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Organocatalyzed Asymmetric Michael Addition of 4-Monosubstituted-pyrazol-5-ones to Enones: Construction of Vicinal Quaternary and Tertiary Stereocenters Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-15 Pooja Goyal, Akhil K. Dubey, Raghunath Chowdhury
Pyrazolone moiety bearing an all-carbon quaternary stereogenic center is frequent in biologically active products and pharmaceuticals. The catalytic route for the construction of a quaternary carbon center possesses challenges. In this report, catalytic asymmetric Michael addition of 4-monosubstituted-pyrazol-5-ones to simple enones catalysed by primary amine-Brønsted acid composite has been developed
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Effects of a Larger N‐Heterocyclic Ring in Rofecoxib Analogues on AIE Activity and Multifunctional Applications Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-16 Wei Liu, Yinyin Yao, Yanbing Ke, Jingming Zhou, Weiwei Zhang, Renfu Li, Yusheng Lu, Hong Jiang, Lijun Xie
Two analogues of rofecoxib, 2‐Pyr‐ROF and 2‐Pip‐ROF, were designed according to the strategy of heterocyclic ring enlargement and facilely synthesized in a facile manner by Knoevenagel reactions. The first compound, 2‐Pyr‐ROF, had low quantum yields (QY) of 3.0% in the solid states. After replacing the pyrrolidinyl with piperidinyl, the resulting 2‐Pip‐ROF had a significantly increased QY, with a value
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Investigations on Superbase Mediated Reactivity of N‐Tosylhydrazones with Aza‐ortho‐Quinone Methide Precursors Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-16 Rahul P., Arunkumar T. K., Seena Sebastian, Haritha Raveendran, Sunil Varughese, Jomon Mathew, Jubi John
We have encountered a superbase‐mediated chemoselective reaction of N‐tosylhydrazones with aza‐ortho‐quinone methide precursors. When tosylhydrazone was treated with ortho‐aminobenzyl alcohol in super basic conditions (KOH+DMSO), we observed the formation of 2‐substituted quinoline. The reaction was found to be general, and by this method, mono‐, di‐ and tri‐substituted quinolines could be made. We
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Visible‐Light Promoted Minisci–Type Cyanoalkylation of Azauracils via C‐C Bond Cleavage Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-16 Chengli Xiang, Sheng Yu, Haiyang Fei, Changduo Pan, Jin-Tao Yu
A photo‐induced Minisci–type cyanoalkylation of azauracils was developed under metal‐free and base‐free conditions. Readily available cyclobutanone oxime esters were used as the cyanoalkylating reagents via C‐C bond cleavage to generate the γ‐cyanoalkyl azauracil derivatives in good to moderate yields. The introduced cyano group can be easily converted into many other functional groups, thus makes
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Molybdenum‐Catalyzed One‐Pot Multi‐Step Synthesis of N‐Polyheterocycles from Nitroarenes and Glycols Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-16 Sara Gómez-Gil, Nuria Cases, Raquel Hernández-Ruíz, Rubén Rubio-Presa, Samuel Suárez-Pantiga, María R. Pedrosa, Roberto Sanz
We report the efficient, sustainable one‐pot synthesis of a wide variety of N‐polyheterocycles, such as imidazo‐quinolines and quinoxalines, and furoquinolines, from easily available nitroaromatics and glycols via a molybdenum catalytic domino reduction‐imine formation‐intramolecular cyclization‐oxidation sequence. It is worth highlighting that the recycling and incorporation of the waste carbonyl
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Dynamic Covalent Synthesis Applied to Optoelectronic and Energy Materials: Design, Applications and Limitations Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-16 Elarbi Chatir, Arthur David, Adèle Gapin, Antoine Goujon
Dynamic Covalent Chemistry, consisting in the use of dynamic covalent bonds (DCBs) to create complex objects by working at the thermodynamic equilibrium, has undeniable advantages for the preparation of conjugated systems with tailored optoelectronic properties for organic electronics. Chemists can combine simple building blocks with simple functional groups of appropriate geometry, structure and stoichiometry
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Synthesis of β‐Aryl‐α,β‐Dehydroaminophosphonates by Pd‐Catalyzed Fujiwara–Moritani C−C Coupling Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-16 Javier Sáez, David Dalmau, Francisco J. Sayago, Esteban P. Urriolabeitia
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Base‐Regulated Synthesis of the Bestmann‐Ohira or Seyferth‐Gilbert Reagent Utilizing FSO2N3 Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-14 Shuo Liu, Yufei Liang, Long Xu, Jiajia Dong
Herein, we present a new application of fluorosulfonylazide (FSO2N3) for diazotizing a series of activated methylene compounds to deliver the corresponding diazo products. Notably, by the judicious choice of bases, the selective generation of the Bestmann‐Ohira reagent (BOR) or the Seyferth−Gilbert reagent (SGR) has been realized from FSO2N3 and dimethyl‐2‐oxopropylphosphonate. We also investigated
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Synthesis of Artemisinin G from Artemisinin via Photocatalysis Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-14 Menghan Wang, Xiaoling Liu, Xiaoshan Zheng, Yining Luo, Yu Gao, Haijun Chen
Photoredox catalysis has become a mainstay in synthetic methodology over the past decade. However, its versatility for the development and functionalization of natural products remains further exploration. Herein, we report an efficient approach to synthesize artemisinin G by using TBADT as the efficient initiator under mild conditions.
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Practical and Divergent Synthesis of Carbocyclic Pyrazolo[3,4‐d]pyrimidine Nucleoside Analogues Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-14 Ewout Van de Velde, Anouk Van Hauwermeiren, Natascha Van Pelt, An Matheeussen, Guy Caljon, Serge Van Calenbergh
A concise set of 4‐substituted pyrazolo[3,4‐d]pyrimidine carboriboside analogues was synthesized in a divergent fashion through a central intermediate. An oxaziridine reagent allowed to synthesize a crucial hydrazine glycon intermediate, which was transformed via a base build‐up strategy to the desired intermediate using a commercially available pyrimidine building block. Reaction with a variety of
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N‐Heterocyclic Carbene–Catalyzed Kinetic Resolution of 3–Nitro–1,2–dihydroquinolines: Asymmetric Synthesis of All C2–, C3– and C4–Functionalized Tetrahydroquinolines Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-14 Pushpendra Mani Shukla, Aniruddh Pratap, Biswajit Maji
An efficient N‐heterocyclic carbene (NHC)‐catalyzed kinetic resolution of 2‐substituted 3‐nitro‐1,2‐dihydroquinolines (DHQs) allowing the synthesis of densely functionalized enantioenriched tetrahydroquinolines through the resolution at remote stereocenter is described. The Re‐face addition of α,β‐unsaturated azolium homoenolate intermediate generated in situ from enal with the more kinetically favored
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CO‐Boosted Protocol for the Photocatalytic C‐H Thiolation of Aldehydes Using Phenylthiobenzenesulfonate Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-13 Lin-Wei Pan, Nobukazu Taniguchi, Mamoru Hyodo, Ilhyong Ryu
The formyl C‐H thiolation of aldehydes using thiosulfonates using the decatungstate anion as a photocatalyst is reported. Using this photocatalytic protocol, both aromatic and aliphatic thioesters can be synthesized in good yields. The transformation consists of a cascade of double SH2 reactions, HAT and an ArS group transfer, and the yields are improved when the reaction is carried out in a CO atmosphere
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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. (IF 2.8) Pub Date : 2024-03-13 Elisa Brambilla, Mariaclara Gugiatti, Silvia Rizzato, Giorgio Abbiati, Valentina Pirovano
We present a method for the synthesis of substituted indolo[1,2‐a]quinoline‐5(6H)‐ones starting from 1‐(2‐ethynylphenyl)‐1H‐indoles. The transformation involves gold‐catalyzed oxidation of the triple bond followed by acid‐promoted intramolecular cyclization at the indole C2 position. Demonstrating noteworthy versatility, the reaction tolerates a wide array of substituents on the indole core and proceeds
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Unsymmetrical Anthracene Platforms as Singlet Oxygen Batteries: Effects of Substituents on Photooxygenation and Endoperoxide Thermolysis Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-12 Paul De Bonfils, Pierrick Nun, Vincent Coeffard
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On the Substrate Scope of Dimethylsulfonium Propionate Lyases toward Dimethylsulfoxonium Propionate Derivatives Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-12 Anuj K. Chhalodia, Jeroen S. Dickschat
The six dimethylsulfonium propionate (DMSP) lyases DddQ, DddW, DddP, DddY, DddK and DddL catalyze the elimination of dimethyl sulfide from DMSP and can also cleave the marine metabolite dimethylsulfoxonium propionate (DMSOP) to DMSO and acrylate. In this study the potency of all six enzymes for the conversion of four DMSOP analogs with longer alkyl chains that were synthesized in three steps from 3‐mercaptopropionic
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Practical and Selective Syntheses of S‐Acyl and N‐Acyl Glutathiones with N‐Acyl Imidazoles in Water Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-12 Michele Retini, Andrea Sisti, Diego Olivieri, Michele Mari, Francesca Bartoccini, Giovanni Piersanti
A selective, mild, convenient, and green protocol for the preparation of S‐acyl and N‐acyl glutathiones is described involving the chemical modification of glutathione (GSH) with N‐acyl imidazoles at room temperature in water. The syntheses of S‐acyl glutathiones were achieved in very high yields using 1 equiv of an N‐acyl imidazole in water at room temperature, without the need of a base. Double acylation
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cis‐Linked Cyclotetraphenylenes: Synthesis, Structures and Fluorescence Properties Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-11 Bo Zou, Jian-An Li, Zaofen Zhai, Taoxing Yu, Haoran Liu, Jieqing Huang, Huowang He, Bingjia Xu, Hua-Wei Jiang
cis‐Linked cyclotetraphenylene dimer [2]c‐CTPE and trimer [3]c‐CTPE were synthesized via Pt‐mediated cyclization of cis‐diboronated tetraphenylethene. The structure of [2]c‐CTPE has been confirmed by single crystal X‐ray diffraction. The strain energy of [2]c‐CTPE and [3]c‐CTPE was calculated to be 86.28·kJ mol‐1 and 9.23 kJ·mol‐1, respectively. [2]c‐CTPE and [3]c‐CTPE are typical AIEgens and show
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Photo/Electrochemical‐Mediated C(sp3)–H Bond Functionalization of (Thio)Ethers Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-11 Lianglong Sun, Dongyang Zhao, Kai Sun, Fei Liu, Shubing Yang, Si Chen, Xin Wang
Molecules containing ether skeletons are widely present in drugs, natural products, functional materials, and life science. Direct C(sp3)–H bond ether functionalization is considered a powerful strategy for the construction of novel ether derivatives. Photo‐/electro‐chemical technology is a relatively green and sustainable synthesis method, which opens up a broad application prospect in the field of
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Decarboxylative Amination of SMAHOs by Dialkyl Azodicarboxylates Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-09 Marine Pinaud, Erwan Le Gall, Marc Presset
The decarboxylative addition of substituted malonic acid half oxyesters (SMAHOs) to dialkyl azodicarboxylates is described. The reaction was promoted by 1,4‐diazabicyclo[2.2.2]octane (DABCO) as an organocatalyst in heated toluene. High yields of the coupling products were generally obtained, and the scope of the reaction proved rather important with the potential presence of functionalized pending
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Boron‐Based Enantiomerism Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-07 Manfred Braun
Boron‐based enantiomerism is fragile due to the inherent tendency of a dissociation of a ligand from tetra‐coordinate chiral boron complexes under formation of the achiral tri‐coordinate species. This review will present the different approaches in overcoming the inherent tendency of racemization in boron‐stereogenic compounds. When embedded in an environment of chiral ligands or substituents, configurationally
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Palladium‐Catalyzed C8‐Fluoroalkylation and C8‐Fluoroalkenylation of Naphthalenes by C−H Activation Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-07 Hugo Amistadi-Revol, Julie Tremblais, Nicolas Casaretto, Sébastien Prévost
In this study, two novel C8‐functionalization methods of 1‐carbonylnaphthalenes are detailed. Leveraging iodonium triflate as coupling partners, we disclosed palladium‐catalyzed C8‐fluoroalkylation and C8‐fluoroalkenylation processes. These protocols exhibit broad applicability across diverse naphthalene derivatives, thanks to carbonyl directing groups at C1 position which can be retained for subsequent
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Front Cover: Investigation into a Tetrahydroquinazoline Scaffold (Eur. J. Org. Chem. 10/2024) Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-07 Jonathan Jardner, Leah Bantel, Marie Claußen, Jens Christoffers
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Unlocking the Power of Acyl Fluorides: A Comprehensive Guide to Synthesis and Properties. Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-06 Clémence Bonnefoy, Adrien Gallego, Clément Delobel, Betty Raynal, Maxime Decourt, Emmanuel Chefdeville, Gilles Hanquet, Armen Panossian, Frederic R Leroux, Fabien Toulgoat, Thierry Billard
Acyl fluorides have emerged as versatile reagents in various synthetic endeavors, offering a range of advantages over their counterparts, acyl chlorides. This study delves into the properties and reactivity of acyl fluorides, particularly their reaction with amines and alcohols, to elucidate their distinct characteristics. We also introduce a facile and practical synthesis of acyl fluorides from a
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Direct Diels‐Alder Reaction of Biomass‐Derived Furfurol with Maleimides in a Bio‐Based Green Solvent Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-06 Elpida Skolia, Christoforos G. Kokotos
Environmental concern has motivated an inclination to exploit waste and upgrade it into high‐added‐value chemicals. Biomass is an excellent carbon source that provides a variety of raw materials as building blocks, such as furans. Herein, we report the upcycling of furfurol, a known biomass by‐product, through a Diels‐Alder cycloaddition with maleimides that is performed in a green bio‐derived solvent
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Exploitation of Mechanistic Product Selectivity for the Two‐step Synthesis of Optically Active Bio‐derived Cyclic Carbonates Incorporating Amino Acids Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-06 Diego Jaraba Cabrera, Lucía Álvarez-Miguel, Adrián Hernando Rodríguez, Alex Hamilton, Marta E. G. Mosquera, Christopher J. Whiteoak
The synthesis of bio‐derived cyclic carbonates is attracting a lot of attention as the incorporation of bio‐derived functionality into these compounds provides the opportunity to prepare previously unknown structures, whilst also improving their sustainability profiles. This study presents a facile preparation of diastereomerically pure bio‐derived cyclic carbonates displaying a range of optical rotation
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Photoinduced Generation of Active Intermediates from Unmodified 1,3‐Dicarbonyl Compounds for Organic Transformations Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-06 Hao-Yuan Li, Niu Xiaoying, Xiu-Long Yang
Photocatalysis utilizes light as the initial driving force for chemical reactions, enabling reactions with high energy barriers in traditionally thermal chemistry to proceed under mild conditions. 1,3‐Dicarbonyl compounds occur as important active molecules in nature and are intermediates in pharmaceutical syntheses. In recent years, there have been numerous studies of these compounds, and it is common
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C(sp2)‐H Imination of Imidazo[1,2‐a]pyridines: A Catalyst‐Free, Multicomponent Approach Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-05 Yadavalli Subba Rao, Doma Arun, Nagaraju Devunuri, Srinivasarao Yaragorla
We report here a catalyst‐free, (sp2)C‐H imination reaction of in‐situ formed imidazo[1,2‐a]pyridines and a‐iminoketones. This one‐pot, multicomponent, and atom economic reaction is performed at moderate to room temperature without the need for any catalyst and inert conditions. The reaction showed good substrate tolerance with appreciable yields. Gram‐scale synthesis and post‐synthetic modifications
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Stereoselective Total Synthesis of Pyranicin and 4‐epi‐Pyranicin from Carbohydrate Precursors Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-05 Praveen Ambati, Akanksha Gupta, Anjaneyulu Bandi, Perali Ramu Sridhar
Herein, we describe a simple and efficient pathway for the total synthesis of pyranicin and 4‐epi‐pyranicin by utilizing carbohydrates as chiral raw materials for the first time. The general synthetic strategy involves the formation of two main fragments: Fragment 1 is the central tetrahydropyran core, which was constructed in a total of 10 steps from 2,3,4,6‐tetra‐O‐acetyl D‐glucal via Ferrier‐type
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Polyhalogenated Carbohydrates: Synthesis and Applications of Sugar Halides from Fluorine to Iodine Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-05 Olivier Lessard, Danny Lainé, Denis Giguére
Polyfluorinated carbohydrates have attracted attention in the last decades. This is due to the interesting properties of such organofluorines. What about the other halogens? Since the discovery of sucralose (a trichlorinated disaccharide) more than 50 years ago, only a handful of chlorinated, brominated, or iodinated carbohydrates have been reported. This review focuses on the synthesis of polyhalogenated
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Metal‐Free ipso‐Halocyclization of N‐arylpropynamides Using Hypervalent Iodine(III) Reagents under Aqueous Condition Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-05 Pankaj Jangir, Kalu Ram Bajya, Akshay Pathare, Mohammad Sodoor, Rinku Saini, Mukesh Purohit, Sermadurai Selvakumar
We report, an intramolecular ipso‐halocyclization of N‐arylpropynamides using readily available hypervalent iodine reagent as mild oxidant and alkali halides like KCl, KBr, and KI as the halogen source. Using this method, a broad range of valuable halogenated spiro[4.5]trienones can be obtained in an excellent yield at room temperature. Notably, this protocol doesn’t require para‐substituents such
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Selective Transformation of 1,3-Cyclooctadiene into Novel Functionalized Azaheterocycles, β-Amino Esters, and Lactams by Means of Ring-Rearrangement Metathesis Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-04 Anas Semghouli, László Drahos, Balázs Volk, Loránd Kiss
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Synthesis and Properties of Azadibenzo[a,e]pyrenes Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-04 Aleksandra Khomutetckaia, Peter Ehlers, Alexander Villinger, Peter Langer
Four different isomeric azadibenzo[a,e]pyrenes (benzo[4,10]anthra[9,1‐gh]isoquinolines and benzo[4,10]anthra[1,9‐fg]isoquinolines) were prepared by combination of Pd‐catalyzed Sonogashira and Suzuki cross‐coupling, Brønsted acid mediated cycloisomerization and Pd‐catalysed CH‐activation reactions. The optical properties have been studied by steady‐state absorption and emission spectroscopy in different
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Co‐Catalyzed Peroxidation of Cyclic β‐Dicarbonyls Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-04 Oleg V. Bityukov, Pavel Yu. Serdyuchenko, Vera A. Vil’, Gennady I. Nikishin, Liang-Nian He, Alexander O. Terent'ev
A Co‐catalyzed peroxidation of cyclic β‐dicarbonyls (cyclic 1,3‐diketones, 4‐hydroxy‐2(5H)‐furanones and Meldrum’s acids) with TBHP has been disclosed. A series of the alkylperoxy derivatives of 4‐hydroxy‐2(5H)‐furanones and Meldrum’s acids were synthesized in moderate to good yields (13‐86%). The functionalization of 4‐hydroxy‐2(5H)‐furanones by the tBuOO group was performed with high selectivity
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Cyclodextrin‐Based Catenanes Platformed with meso‐Arylporphyrin Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-04 Kaoru Asai, Qiyue Mao, Atsuki Nakagami, Hiroaki Kitagishi
Among mechanically interlocked supramolecular systems with cyclodextrins (CDs), successful examples of CD‐based catenanes are limited compared to a number of CD rotaxanes owing to the synthetic difficulties. We herein demonstrate an efficient synthesis of a CD‐based catenane using a meso‐arylporphyrin (Por) platform. Using Por modified with two olefin‐terminated oxyethylene chains at the cis‐meso‐positions
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Synthesis of Bicyclo[1.1.1]pentane Carboxamides and Ketones from [1.1.1]Propellane Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-04 Min Ling, Mengke Chen, Qian Jiang, dongping cheng, Jing-Hua Li
Bicyclo[1.1.1]pentane (BCP) carboxamides are prepared from the direct addition of [1.1.1]propellane with semicarbazides in the presence of iron(II) phthalocyanine {Fe(Pc)} and tert‐butyl hydroperoxide (TBHP) in moderate to good yields. BCP ketones are also obtained under similar conditions in moderate yields. This protocol provides a straightforward one‐step access to BCP carboxamides, synthesis of
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Recent Advances of 2‐Nitroglycals as Powerful Glycosyl Donors Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-02 Xinxin Li, Lei Deng, Liming Wang, Qingju Zhang
2‐Nitroglycals are important synthons for biological active 2‐aminoglycosides, glycoconjugates and natural products synthesis. Herein, we summarized the recent advances of 2‐nitroglycals including its synthetic methods and its applications. Using 2‐nitroglycals, 2‐aminoglycosides, nitro‐polyol derivatives, sugar‐furan derivatives, sugar‐pyrrole molecules, 2,3‐diaminoglycosides and 2‐amino‐1,3‐dithioglycosides
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TBAI‐catalyzed, TBHP‐mediated Modular Three‐Component Cascade towards Highly Functionalized Pyrrole via [3+2] Annulation Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-01 Karthiyayini Gnanaoli, Deepan Babu Rajkumar, Keerthana Gopal, B Saritha, C Uma Maheswari
A facile, one‐pot sequential synthesis of highly substituted pyrrole employing TBAI/TBHP has been developed from readily available precursors. β‐Enaminones generated in situ from β‐ketoesters and primary amines react sequentially with electron‐deficient alkynes via a radical pathway to form the penta‐substituted pyrroles in moderate to good yields. This strategy for the synthesis of highly functionalized
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Mechanistic Insights into Urea‐, Thiourea‐, and Isothiourea‐Based Bifunctional Tetraarylphosphonium Salt Catalysis for Conversion of Carbon Dioxide to Cyclic Carbonates Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-29 Yasunori Toda, Daiki Suenaga, Ren Yamaguchi, Hiroyuki Suga
A novel bifunctional isothiourea derived from a tetraarylphosphonium salt catalyzes the coupling reaction of monosubstituted epoxides with 1 atm of carbon dioxide to afford five‐membered cyclic carbonates in high yields. Thiourea and urea groups are also effective hydrogen bond donors for the carbon dioxide fixation. Comprehensive mechanistic studies on this catalysis using theoretical calculations
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Cp2Fe‐Mediated Electrochemical Synthesis of Functionalized Compounds: Recent Advances Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-29 Ranran Zhu, Dumei Ma, Yufen Zhao, Ju Wu
Unlike traditional organic methods, electrosynthesis has emerged as an environmentally friendly and sustainable approach to generate a series of functionalized compounds. In this process, the traceless electron serves as the redox agent, eliminating the need for stoichiometric oxidants or reductants. In contrast to direct electrolysis, redox‐mediated electrolysis has the ability to overcome kinetic
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One‐Pot Synthesis of 2‐(Alkylsulfanyl)quinolines from Aryl Isothiocyanates and Allenes or Alkynes Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-29 Nina Nedolya, Olga Tarasova, Alexander Artem’ev, Alexander Albanov, Irina Bagryanskaya, Boris A. Trofimov
In this work, a conceptually novel approach to diversely substituted 2‐(alkylsulfanyl)quinolines is described. The approach includes the assembly of the target molecules from allenic or acetylenic carbanions, aromatic isothiocyanates, and alkylating agents, The process proceeds in a single synthetic operation via the formation and 6π‐electrocyclization of N‐aryl‐1‐aza‐1,3,4‐trienes, R2R3C=C=C(R1)C(SAlk)=NAr
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Benzocoumarin-Fused Triskelions Exhibit AIEE Due to Inhibited Molecular Inversion Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-28 Masafumi Ueda, Midori Kuramochi, Riho Shimizu, Yuki Ohba, Norifumi Yamamoto, Yasuhiro Mazaki
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Reactivity of Electrophilic Trifluoromethylating Reagents Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-28 Daria S. Timofeeva, Ángel Puente, Armin Ofial, Herbert Mayr
Kinetics of the reactions of colored carbanions (reference nucleophiles) with S‐(trifluoromethyl)dibenzothiophenium ions (Umemoto’s reagents) and hypervalent trifluoromethyl‐substituted iodine compounds (Togni’s reagents) have been determined photometrically using stopped‐flow techniques. The second‐order rate constants k2(20 °C) for the reactions of Umemoto’s sulfonium ions (generation I and II) with
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Simple and Efficient Method for Mono- and Di-Amination of Polypyridine N-Oxides Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-28 Wessel Verbeet, Yurii Husiev, Sylvestre A. Bonnet
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Nitrile Furanics via Copper-Catalyzed Dehydration of Aldoximes and Knoevenagel Condensation Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-28 Mattia Annatelli, Chaimaa Sadraoui, Giacomo Trapasso, Fabio Aricò
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Kinetic Resolution of a Planar‐Chiral [2.2]Paracyclophane via Michael Addition to Nitroolefins Catalyzed by N‐Terminal Guanidinylated Helical Peptide Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-27 Jiaqi Tian, Kenya Tamaribuchi, Isao Yoshikawa, Kazuaki Kudo
Kinetic resolution of 4‐(2‐nitrovinyl)[2.2]paracyclophane based on N‐terminal‐guanidinylated resin‐bound helical peptide catalyzed asymmetric Michael addition of malonate esters was developed. This approach provides a new pathway to enantiopure paracyclophane derivatives characterized by both planar and central chirality, along with the recovery of the chiral substrate with a selectivity factor of
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Photoinduced Radical Borylation of Alkyl Chlorides Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-27 Lutao Bai, Lei Jiao
The traditional method for the preparation of alkylboronic esters involves transition metal catalysis or transition metal‐free methods relying on single electron transfer. Each method relies on the suitable choice of catalyst or electron transfer mediator. In this study, we have developed a new method for the synthesis of alkylboronic esters from alkyl chlorides and diboron(4) compounds, without the
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NIS/TEMPO‐Promoted Oxidative Cyanation and Nitro‐Mannich Reaction of Tertiary Amines Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-26 Bulunuer Yusan, Adila Amuti, Xiu Juan Xu, Abudureheman Wusiman
A metal‐free N‐iodosuccinimde (NIS)/2,2,6,6‐tetramethylpiperidinyloxy (TEMPO)‐promoted protocol was developed for the oxidative α‐cyanation and nitro‐Mannich reaction of tertiary amines via a cross‐dehydrogenative coupling reaction under mild conditions. Several control experiments were performed; the coupling reaction outcomes indicated that the C‐N coupled intermediate (N‐Mannich base) formed from
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Direct ortho-Selective Amination of Naphthols with Nitroarenes through Transfer-Hydrogenation Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-25 Renchao Ma, Ruiqin Zhang, Huili Xia, Lei Wang, Yongmin Ma
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Hydroxymethyl-Substituted Tetrathiatriarylmethanol with Variable Reactivity: Selective Access to Three Different Trityl Radicals by Unique Acid-Mediated Reactions Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-24 Yande Gao, Meirong Feng, Longfei Gao, Yurui Leng, Guifang Han, Yuguang Song, Yangping Liu
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Boron Complexes of Tridentate Acyl Pyridylhydrazones Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-23 Alexander E. R. Watson, Paul D. Boyle, Paul J. Ragogna, Joe B. Gilroy
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Synthesis, Structures, Electrochemical and Optical Properties of Vinyl-Extended Tetrathiafulvalene Derivatives Functionalized with Two 2,6-Dicyano-λ5-Phosphinine Units Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-22 Tomoya Misaki, Aya Yoshimura, Takashi Shirahata, Minoru Hayashi, Yohji Misaki, Daisuke Sakamaki, Hideki Fujiwara
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Nitration of Pyrrolo[2,1-a]isoquinolines with NaNO2/HFIP Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-22 Xiang Huang, Yun-Meng Li, Jing Zhou, Yu-Yi Pan, Wei Li, Xiao-Hui Chen, Xin Yu, Shu-Chen Pei, Hai-Lei Cui
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CAN Interceded Oxidative Coupling of β-Dicarbonyl Compounds to 2-Aryl/Heteroarylchromenes: A Regio- and Diastereoselective Synthesis of Tetrahydro-benzofuro[3,2-c]chromenones Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-21 Sayanwita Panja, Arun Dhurey, Gourhari Maiti, Animesh Pramanik
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Thiophane-Catalyzed Umpolung of N-Bromoimides for Dibromination of Olefins Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-02-20 Miao Wang, Teng Niu, Changming Xu