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Iron‐Based Deep Eutectic Solvents: Key Players for Amide and Sulfonamide Synthesis and Alcohol Oxidation Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-22 Luciana Cicco, Sara Urselli, Claudia Favia, Filippo Maria Perna, Paola Vitale, Vito Capriati
A sustainable protocol has been devised for the oxidation of activated secondary alcohols to their corresponding carbonyl compounds, as well as their utilization as selective mono‐alkylating reagents for both amide and arylsulfonamide derivatives. These reactions proceed smoothly and in good yields (up to 98%) when conducted in Fe‐based deep eutectic solvents (DESs), which serve dual roles as solvents
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Activation/Cyclization of 2H‐Azirines and 3‐Amino‐2‐fluoropyridines Towards 2‐Aryl‐Pyrido[2,3‐b]pyrazines Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-22 Tess Fortier, Audrey Belouin, Frédéric Vuillermet, Joanick Bourret, Guillaume Pelletier
The electrophilic activation of 2H‐azirines with triflic anhydride (Tf2O) for an addition/cyclization reaction producing 2‐aryl‐pyrido[2,3‐b]pyrazines regioselectively is described. This reaction proceeds via nucleophilic addition of 3‐amino‐2‐fluoropyridines onto 1‐trifloyl‐aziridin‐2‐yl triflates and subsequent cyclization via SNAr. Desulfonylation and oxidation provides a single regioisomer of the
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Fluoroalkoxylating Reagents in Organic Synthesis: Recent Advances Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-22 Quande Wang, Mingxi Chen
The fluoroalkoxy groups (ORf) are widely used motifs in pharmaceutical and agrochemical fields due to their unique physicochemical properties including higher lipophilicity and increased metabolic stability. Thus, the high value of ORf‐containing derivatives has stimulated the development of fluoroalkoxylation reactions. In this review, we highlight the recent progress of various trifluoroalkoxylating
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Transition‐Metal‐Free Carbonyl Reduction and Hydrodefluorination of β‐Trifluoromethyl Enones with Hydrosilanes: Synthesis of gem‐Difluorovinyl Alcohols Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-20 Peng-Yuan Zhang, Ya-Fei Hu, Jia-Hao Chu, Ren-Jun Zheng, Mengtao Ma, Zhi-Liang Shen, Xue-Qiang Chu
A transition‐metal‐free tandem carbonyl reduction and hydrodefluorination of b‐trifluoromethyl enones with hydrosilanes was developed for the synthesis of a variety of valuable gem‐difluorovinyl alcohols. The hydrosilane could act as both a reductive agent and a C(sp3)‐F bond‐breaking promotor under mild reaction conditions. Synthetically useful organofluorides, such as gem‐fluorophosphine alkene,
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Copper‐Promoted Oxidative Amidation of Imines: A Facile Route to Amides Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-20 Zhonghua Cao, Da Sheng, Zhiyang Zhang, Haitao Ren, Yong Liu, Songhai Wu, Jiaxiang Zhang, Xu Han
Herein, an environmentally friendly and efficient amidation method of imines by Oxone and CuO has been developed. This facile method shows excellent selectivity without affecting other functional groups such as phenyls, halogens, cyans, esters or heterocycles. This method features a broad substrate scope, mild conditions and high yields (≤90%), and the yield in the gram scale experiment also reaches
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Pd‐catalysed indirect and regioselective phosphonation of azobenzenes: toward the design of water‐soluble photoswitches Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-19 Ivanna AMARSY, Nicolas Gigant, Izel Erturk, Nicolas Bogliotti, Delphine JOSEPH, Sandrine Delarue-Cochin
An efficient palladium‐catalysed ortho C‐H acyloxylation of azobenzenes, allowing the introduction of the difunctionalised substituent, diethyl phosphonoacetate, is reported. Thanks to the mild reaction conditions implemented, this regioselective late‐stage ortho‐functionalisation tolerates a wide range of functional groups and permits the access of diversely substituted azobenzenes in good to excellent
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Expression of Concern: One‐Step Synthesis of Biaryls under Mild Condotions Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-19
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Synthesis of Noncoded Amino Acids Bearing a Salicylaldehyde Tag for the Design of Reversible‐Covalent Peptides Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-19 Mattia Mason, Beatrice Nava, Laura Belvisi, Luca Pignataro, Alberto Dal Corso
Insertion of electrophilic species on the structure of small molecule ligands or peptides is a well‐known strategy to increase their binding affinity for the target protein of interest. Among these reactive units, the salicylaldehyde (SA) tag can form remarkably stable imine bonds with the ε‐amino group of lysine, a highly frequent residue in proteins. In this work, we describe the optimized synthesis
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Structure‐Activity Relationships of Glucose‐based PdII‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-18 Hannes Ziems, Mirai Komabayashi, Paul Lehmann, Alexander Villinger, Stefan Jopp
The authors of this work have optimized a novel synthetic route towards glucose‐based PdII‐bis(NHC) complexes in only 4 steps with total yields up to 73 %. The synthesis route encompasses an Appel reaction towards 6‐iodo‐glucopyranosides, followed by acyl‐protection, then quaternization with imidazoles and finally the conversion of these acyl‐protected glucosyl imidazolium salts to their respective
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Catalyst‐free Chloroamination Cyclization Cascade with Sodium Hypochlorite: from N‑(Pentenyl)sulfonylamides to 2‑(1‐Chloromethyl)pyrrolidines Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-18 Jacopo Scarfiello, Marco Rusconi, Alberto Lanfranco, Emanuele Azzi, Stefano Caracciolo, Giovanni Ghigo, Polyssena Renzi, Annamaria Deagostino
A mild and catalyst‐free protocol to obtain several 2‐chloromethylpyrrolidines by the use of a commercial solution of sodium hypochlorite is here reported, without the need for a light source. The choice of the solvent revealed to be crucial in the success of the reaction. Mechanistic studies, both experimental and computational, confirmed a radical mechanism, where the deprotonation step, followed
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Front Cover: A Green Approach to Nucleophilic Aromatic Substitutions of Nicotinic Esters in Cyrene (Eur. J. Org. Chem. 15/2024) Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-18 Andrea Citarella, Miriam Cavinato, Arianna Amenta, Marco Nardini, Alessandra Silvani, Daniele Passarella, Valerio Fasano
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Iridium‐Catalyzed Electrooxidative Annulation of Naphthol with Acrylate via C‐H Bond Activation for the Synthesis of Naphtho[1,8‐bc]furan Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-17 Nilam Patil, Debarati Das, Bhalchandra Mahadeo Bhanage
Iridium catalyzed electrochemical coupling of naphthols with acrylates for the syntheses of naphtho[1,8‐bc]furan derivatives are herein reported. Ir‐catalyzed electrochemical C‐H annulation is accomplished within a supportive catalysis manifold, paving the way for electrooxidative C‐H acrylation via weak O‐coordination. The merge of iridium catalysts and electric current not only minimizes the need
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Enantioselective Synthesis of Sterically Hindered α‐Allyl‐α‐Aryl Lactams via Palladium‐Catalysed Decarboxylative Asymmetric Allylic Alkylation Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-17 Declan Galvin, Patrick Guiry
The Pd‐catalysed decarboxylative asymmetric allylic alkylation (DAAA) of sterically hindered α‐aryl,β‐amido allyl ester lactams has been developed. The key step in the synthesis of a range of α‐aryl lactam substrates for catalysis was a Pb‐mediated α‐arylation of a β‐amido allyl ester affording 14 novel examples of α‐aryl‐β‐amido allyl ester lactams in good yields (up to 80 %). The Pd‐catalysed DAAA
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Three‐Component Reactions of Alkenes with C–C Bond Formation: Recent Developments Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-17 Zhanyong Wang, Jiarong Li, Tingan Li, Xiaoying Jiang, Hang Li, Ziyan Zhang, Shaohong Xu
Alkenes are highly valuable materials in organic synthesis, and their three‐component reactions offer a promising method for C‐C bond formation and carbon chain elongation. This approach not only reduces the number of reaction steps but also minimizes waste generation, enabling the preparation of polysubstituted alkanes from simple starting materials. In this review, we provide an overview of recent
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Synthesis and Application of Well‐Defined Fluoroalkyl Zinc Complexes Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-17 Cai Zhang
Fluoroalkyl groups play an irreplaceable role in the field of pharmaceutical and agrochemical industry due to their unique properties. Based on this, it is crucial to effectively introduce fluoroalkyl groups into target molecules. In this review, we describe the synthesis of well‐defined fluoroalkyl zinc complexes and their applications in the fluoroalkylation of compounds. Different from the reactivities
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Fluorene and Fluorenone Unnatural Amino Acid Motifs via Diastereoselective Pd(II)‐Catalyzed sp3 C‐H Functionalization Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-17 Shefali Banga, Srinivasarao Arulananda Babu
This paper reports the construction of racemic and enantiopure (D‐ and L‐) fluorene and fluorenone‐based novel unnatural amino acid derivatives. The Pd(II)‐catalyzed bidentate directing group‐aided arylation of prochiral β‐C(sp3)‐H bonds in racemic, enantiopure carboxamides of amino acids with iodofluorenes was reported. The construction of novel examples of fluorene and fluorenone motifs containing
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Decatungstate‐Photocatalyzed Diastereoselective Dearomative Hydroalkylation of Indoles Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-16 Emeric Montinho-Inacio, Damien Bouchet, Wei-Yang Ma, Pascal Retailleau, Luc Neuville, Géraldine Masson
In this study, we present an efficient and straightforward dearomative hydroalkylation of indoles. By utilizing alkanes or ethers as alkyl radical sources and employing TBADT as a cost‐effective photocatalyst for direct hydrogen atom transfer (HAT), we achieved successful conversion of these heterocyclic derivatives into 2‐alkylindolines with good to excellent yields and high diastereoselectivity under
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Application of the Photo‐Fries Reaction as a Key Step in the Preparation of Valuable Aryloxyethyl Selenocyanates Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-16 Valentin Lucena, Sergio Hernán Szajnman, Juan Bautista Rodriguez, Sergio Mauricio Bonesi
A multi‐step sequence leads to the preparation of a series of aryl selenocyanate WC‐9 homologues which are interesting compounds with potential biological activity against Trypanosoma cruzi, the etiological agent of Chagas disease. The synthetic sequence involves the application of the photo‐Fries rearrangement reaction as a key step for the preparation of a series of 2‐hydroxyphenones bearing alkyl
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Direct Introduction of an Acetyl Group at the α‐Carbon Atom of an Arene Ring through an Amide Photo‐Fries Rearrangement upon Exposure to UV Light Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-16 Myeonggeuk Kim, Ha-Na Na, Liu-lan Shen, Jin Hyun Jeong
We employed amide photo‐Fries rearrangement for the synthesis benzoheterocyclic compounds and found that a direct acylation of α‐carbon in an arene ring can occur upon exposure to ultraviolet (UV) light. In this reaction, the N‐acetyl group of amides underwent rearranged to the α‐position cross the bridgehead carbon to the other side of the carbon under UV‐C light. The reaction conditions were gentle
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Transfer Hydrogenolysis of O‐ and N‐Benzyl Groups in Water with Tetrahydroxydiboron by Using an Amphiphilic Polymer‐Supported Nano‐Palladium Catalyst Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-16 Kaili Zhang, Shintaro Okumura, Yasuhiro Uozumi
Debenzylation of O‐ and N‐benzyl groups was achieved under safe and mild conditions by using B2(OH)4 as an alternative to gaseous hydrogen in the presence of an amphiphilic polystyrene–poly(ethylene glycol) resin‐supported nano‐palladium catalyst (ARP‐Pd) in water. Benzyl groups of a variety of benzylic ethers, esters, carbamates, and amines, including benzyl‐protected carbohydrates and amino acids
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New Avenues for the Synthesis of Oxa‐Cycles Using Lewis/Brønsted Acid mediated Carboxygenation and Carboalkoxylation of Alkynes Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-16 Santosh Kumar Nanda, Laxmi Narayan Nanda, Juhi Pal, Santosh J. Gharpure
The cascade functionalizations of alkynes have provided many elegant methods for the synthesis of useful scaffolds. Amongst these functionalizations, the ones comprising C‐C and C‐O bond formation have been utilized extensively due to the abundant presence of oxygenated motifs in various bio‐active natural as well as unnatural products. Transition‐metal catalysis is a mainstay for these tandem functionalizations
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Novel Ferrocenyl‐azole Derivatives: Synthesis, DFT Calculation and Unlocking the Anticancer Potential Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-16 Vijesh Tomar, Parveen Kumar, Deepak Sharma, Tejveer Singh, Meena Nemiwal, Raj Kumar Joshi
Herein, a series of novel ferrocenyl/phenyl/thiophenyl‐azoles was disclosed by vinylic amination of ferrocenyl/phenyl/thiophenyl substituted β‐chloro cinnamaldehydes and acrylonitriles. A highly economical and robust chalcogen‐stabilized iron selenide carbonyl cluster Fe3Se2(CO)9 worked as an efficient catalyst under aerobic conditions. The amination of ferrocenyl/phenyl/thiophenyl substituted β‐chloro‐vinylic
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Cyclopropanation of Aryl and Styryl Acetonitriles With Selenium‐Based Dielectrophiles. Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-15 Italo Franco Coelho Dias, Giulia Allegrini, Ewelina Wielgus, Józef Drabowicz, Eder João Lenardão, Luana Bagnoli, Claudio Santi, Francesca Marini
Efficient cyclopropanation reactions of aryl or styrylacetonitriles with vinyl selenones under mild conditions were described. By this approach, synthetically challenging 1‐vinylcyclopropane‐1‐carbonitriles were accessible in good yields. This methodology features the advantage of operational simplicity, broad substrate scope, good functional group tolerance, transition‐metal‐free conditions, mild
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Photo‐Induced Cross‐Dehydrogenative Coupling of Quinoxalin‐2(1H)‐ones with Aldehydes under Metal Free Conditions without an External Photocatalyst Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-12 Chunmiao Wang, Jiangtao Jiang, Min Wang, Weichang Zhu, Pinhua Li
A mild strategy to 3‐acylated quinoxalin‐2(1H)‐ones via a photo‐induced cross‐dehydrogenative coupling of quinoxalin‐2(1H)‐ones with commercially available aldehyde under metal free conditions without an external photocatalyst was developed. In this transformation, various 3‐acylated quinoxalin‐2(1H)‐ones were generated in high yields with good functional‐group tolerance.
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A Microwave‐Assisted One‐Pot Three‐Step Metal‐Free [4+2] Annulation for the Sustainable Synthesis of Highly Substituted 1,2,4‐Triazines Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-12 Daniele Rubini, Maria Grazia Martina, Matteo Incerti, Francesca Barbieri, Marco Radi
Herein we report the first microwave‐assisted one‐pot three‐step metal‐free [4+2] procedure for the synthesis of 5,6‐substituted‐3‐hydrazinyl‐1,2,4‐triazines directly from commercially available aromatic and heteroaromatic ketones. The 3‐hydrazinyl‐1,2,4‐triazine can be isolated or further elaborated, after a simple work‐up, by direct condensation with different aldehydes or ketones to provide highly
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Atroposelective Construction of Naphthylpyrazoles by Chiral Phosphoric Acid Catalyzed Enantioselective Cross‐Coupling of Pyrazoles with Naphthoquinone Esters Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-10 Xi Luo, Sen Li, Yuting Tian, Yuqi Tian, Limei Gao, Qiang Wang, Yongsheng Zheng
The catalytic asymmetric reaction of 5‐aminopyrazoles with naphthoquinone esters has been established. A wide range of unprecedented axially chiral naphthyl‐pyrazole derivatives (29 examples) have been synthesized in moderate to excellent yields (up to 99% yield) with excellent enantioselectivities (up to 99% ee) by utilizing chiral phosphoric acid as a catalyst. This protocol features mild reaction
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Nickel‐Catalyzed Branch Selective C‐H Alkylation of Indoles and Azoles with Alkenes: An Additive‐ and Solvent‐Free Approach Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-10 Shidheshwar B. Ankade, Shuvajit Baneerjee, Benudhar Punji
The development of sustainable protocols for the synthesis of alkylated heteroarenes is crucial owing to their widespread existence in medicinally relevant and bioactive natural products. Herein, we describe an efficient, additive‐ and solvent‐free approach for the regioselective C−H alkylation of indoles and azoles with alkenes using a nickel catalyst, which proceeds through a chelation‐assistance
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n‐Bu4NI/K2S2O8‐Mediated C–N Coupling between Aldehydes and Amides Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-10 Xiaochen Liu, Samual Hee, Netanel G. Sapir, Alvin Li, Syed Farkruzzaman, Jianbo Liu, Yu Chen
n‐Bu4NI/K2S2O8‐mediated C‐N coupling between aldehydes and amides is reported. A strong electronic effect is observed on the aromatic aldehyde substrates. The transformylation from aldehyde to amide takes place exclusively when an aromatic aldehyde bears electron‐donating groups at either the ortho or para position of the formyl group, while the cross‐dehydrogenative coupling dominates in the absence
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Oxygen‐Bridged Quasi‐Planar para‐Phenylenediamine and Its Oxidized States Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-10 Koshi Yoshida, Kai Hikida, Takayuki Tanaka, Shu Seki, Akihiro Ito
A quasi‐planar N, N, N’,N’‐tetraphenyl‐para‐phenylenediamine, where all the phenyl rings are tethered by four oxygen atoms to embed quasi‐planar triphenylamine moieties into the molecular skeleton, was prepared and characterized to evaluate the impact by incorporating the structural rigidity. The monocationic and dicationic species could be selectively generated, depending on the type of oxidizing
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Systematic Investigation of Optical and Chiroptical Properties of Chiral π‐Conjugated Oligomers in Solution and Thin Films Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-09 Gianluigi Albano, Andrea Taddeucci, Francesco Zinna, Laura Antonella Aronica, Gennaro Pescitelli, Lorenzo Di Bari
Four families of structurally related chiral π‐conjugated oligomers bearing a hydroquinone (HQ), 1,5‐dihydroxynaphthalene (Naph), benzo[1,2‐b:4,5‐b’]dithiophene‐4,8‐diol (BDT) or 9H‐carbazole (CBZ) central core, for a total of 11 new compounds, have been synthesized by simple and versatile synthetic strategies involving Pd‐catalyzed cross‐coupling protocols: a Suzuki‐Miyaura reaction, a Sonogashir
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Facile synthesis of hydroquinone linked 3,3’‐steroid dimers via a modified Mitsunobu protocol Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-09 Patryk Klochowicz, Jacek W. Morzycki, Claudia M. Ramírez-Lozano, Rosa Santillan, Dorota Czajkowska-Szczykowska
A successful approach for the construction of steroid dimers with a hydroquinone linker under PBu3/TMAD/Et3N/toluene conditions is described. This study provided a new one‐step methodology for the design and synthesis of bis‐steroidal 1,4‐phenylene diethers using mild and effective reagents.
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Copper‐Catalyzed Formal [4+2] Cycloaddition of Ethynylethylene Carbonates for the Construction of 3,4‐Dihydro‐2H‐benzo[b][1,4]oxazines Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-09 Xinzhe Hu, Haihui Zhu, Xiang Li, Zhengyu Han, Jianwei Sun, Xiaodong Jin, Hai Huang
A formal [4+2] cycloaddition reaction of ethynylethylene carbonates and 2‐aminophenols has been developed for the synthesis of 3,4‐dihydro‐2H‐benzo[b][1,4]oxazines bearing quaternary carbon atoms. The reaction features mild reaction conditions, good functional group compatibility and good yields. Furthermore, when using chiral PyBox ligand, this strategy could also achieve the asymmetric synthesis
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Novel Imidazole‐based Hydrazonoyl Cyanides and Amidrazones Containing N(N,O)‐Heterocycles: Selective Synthesis, Reaction Mechanisms and Preliminary Anticancer Evaluation Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-08 Soraia P. S. Fernandes, Jorge M. Gonçalves, Bruna F. Silva, Eva Q. Pereira, Paulo J. G. Coutinho, Cristina Pereira-Wilson, Alice Maria Dias
Two series of novel hybrid heterocyclic compounds that combine the imidazole ring with bioactive piperidine, morpholine or piperazine heterosystems, through a hydrazone unit, were easily obtained by two competitive pathways. Starting from 5‐amino‐4‐cyanoformimidoyl imidazoles and 1‐aminopiperidine, 4‐aminomorpholine or 1‐amino‐4‐methylpiperazine under mild acidic media led to the selective synthesis
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Hypersensitive Inhibition of Organocatalysts by Halide Salts: Are Two Catalysts Involved in the Mannich Reaction? Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-08 Teppo Leino, Dimitris Noutsias, Kaisa Helttunen, Jani Moilanen, Eeki Tarkkonen, Elina Kalenius, Anniina Kiesilä, Petri M. Pihko
Conformationally flexible tertiary amine—thiourea‐urea catalysts 1 and 2 for the Mannich reaction between imines and malonate esters are efficiently inhibited by quaternary ammonium halides. NMR titrations, isothermal titration calorimetry (ITC) and NOE experiments showed that the catalysts bind chloride and bromide ions with relatively high affinities (K = 103– 105 M–1 in acetonitrile). The halide
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Asymmetric Construction of Bis‐Spirocyclic Pyrazolones Bearing Vicinal Quaternary Carbon Centers Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-08 Mengjie Yang, Aiqi Xue, Xingfu Wei, Yue Huang, Jingping Qu, Baomin Wang
A catalytic asymmetric (3 + 2) cyclization of pyrazolone‐based MBH addudts with alkylidenyl isoxazolones was presented by using DMAP‐derived chiral catalyst, affording bis‐spirocyclic pyrazolones bearing vicinal all‐carbon quaternary stereocenters within an imbedded cyclopentene ring scaffolds, in good yields with excellent stereoselectivities under mild conditions.
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Construction of 3‐Substituted Phthalides via Lewis Acid‐Catalyzed Intramolecular Ring Opening of Aziridines with Esters Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-08 Siyang Xing, Panpan Zhang, Zhen Tian, Jingmeng Yang, Yuhao Pang, Yuanfen Liao, Yang Liu, Kui Wang, Bolin Zhu
A new strategy for the synthesis of 3‐substituted phthalides has been developed via a Lewis acid‐catalyzed intramolecular ring opening of aziridines with esters. Broad substrate scope, good yields and mild conditions made the cyclization reaction very suitable for the rapid construction of libraries of 3‐substituted phthalide compounds.
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Structural and Electronic Impacts of the Axial Substitution at the Phosphorus Center of C(sp3)‐Bridged P‐Heterotriangulenes Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-06 Siegfried Harrer, Johannes Schühle, Christian Neiß, Marina Günthert, Lena Mittmann, Andrea Reule, Jonas Leitner, Frank Rominger, Andreas Görling, Milan Kivala
The structural and electronic properties of the dimethylmethylene‐bridged P‐heterotriangulene have been systematically modulated by functionalization of its phosphorus center. The optoelectronic properties of the obtained derivatives in solution were characterized by UV/Vis absorption and emission spectroscopy, cyclic voltammetry and 31P NMR spectroscopy. The solid state structures were analyzed by
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Efficient Copper‐Free Sonogashira Coupling in Water and under Ambient Atmosphere Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-05 Erika Ghiglietti, Elena Aurora Incarbone, Sara Mattiello, Luca Beverina
Sonogashira coupling is one of the cornerstone Palladium mediated cross coupling reactions, giving a direct and high yield access to symmetric and non‐symmetric alkynes with high tolerance of substituents. The method generally requires the use of CuI as a cocatalyst, an inert atmosphere to protect palladium catalyst, somewhat harsh conditions like prolonged heating and the use of organic solvents due
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Low‐Impact Synthesis of γ‐Lactones Through Photoinduced Baeyer‐Villiger Oxidation of Cyclic Ketones Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-05 Maria Chiara Cabua, Viktoria Velichko, Luca Pilia, Davide Moi, Francesco Secci
A photocatalyzed oxidation of functionalized cyclobutanones to access g‐lactones has been performed in acetonitrile at room temperature, using anthraquinone derivatives as catalysts in the presence of TFA. The best reaction results were obtained by using 3 mol % of 9,10‐anthraquinone as a catalyst under 370 nm irradiation in an O2 environment. The scope and the limitations of this reaction have been
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Scalable Synthesis of Cinnamylamines Via the Heck Reaction: Application in the Synthesis of Abamine, Naftifine and Reboxetine Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-04 Fotini Moschona, Maria Tsitopoulou, Margarita Efstratiou, Maria Koutiva, Gerasimos Rassias
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LabEx SynOrg: Research Institute Dedicated to Molecular Chemistry Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-04 Annie‐Claude Gaumont, Philippe Jubault, Tatiana Besset
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Chiroptical Properties of a Cryptophane Soluble at Neutral pH Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-04 Thierry Brotin, Nicolas Daugey, Marion Jean, Nicolas Vanthuyne, Thierry Buffeteau
This article reports the synthesis of the two enantiomers of a water‐soluble cryptophane 3 enabling cesium and thallium complexation at neutral or basic pH. The two enantiomers of 3 were obtained in a two steps synthesis from cryptophane 4, a molecule decorated with three phenol groups and three other phenol groups protected by benzyl units. The two enantiomers of 4 were isolated from liquid chromatography
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Elucidating the Key Factors in Hydroamination and Defluoroamination Competitions: A DFT Analysis of Reaction between α‐(Trifluoromethyl)styrene and 2‐Pyridones Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-03 Haoran Xu, Yuchen Zhang, Xiao-Song Xue
β‐fluorocarbanions have garnered considerable attention for their dual reactivity in nucleophilic processes and β‐fluorine elimination. Herein, we reported a thorough computational analysis of the reactions between α‐(trifluoromethyl)styrenes and 2‐pyridones to delineate the factors determining protonation or defluorination pathways for the in situ generated β‐fluorocarbanions under varied basic conditions
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Inorganic ligand‐supported copper catalysts catalyzing alkyne coupling reactions Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-03 Mengjie Deng, Ya Xie, Junting Zhou, Da Shi, Sheng Han, Linke Wu, Han Yu
Glaser‐coupled synthesized 1,3‐diyne can participate in the generation of conjugated polymers and is now widely used in organic and polymer synthesis. Currently, the catalysts in coupling are mostly based on the complexation of noble metals with complex organic ligands, which inevitably increases the research cost and storage difficulty. However, polymetallic oxides (POMs), with acidic and redox properties
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Application of DNA‐Conjugated Aryl Diazonium Intermediates in DNA‐Encoded Libraries Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-02 Xiaohong Fan, Xianfeng Li, Yangfeng Li, Yizhou Li
Aryl diazonium intermediates have emerged as highly versatile intermediates in modern organic synthesis and chemical biology, demonstrating remarkable reactivity under mild reaction conditions. Their significance has extended to DNA‐encoded libraries (DELs), where they serve as valuable alternatives to traditional aryl halide‐based cross‐coupling reactions. Aryl diazonium intermediates as N2‐annulation
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Dielectrophilic Approach to Sequential Heterofunctionalization of Ethylene from Vinylthianthrenium Salt Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-02 Giandomenico Magagnano, Valentin Poirier, Filippo Romoli, Dario Corbisiero, Francesco Calogero, Pier Giorgio Cozzi, Andrea Gualandi
Vinyl thianthrenium salt is a compound with interesting electrophilic properties capable of reacting with two distinct nucleophiles. By using b‐keto esters as one of the reaction partners, it is possible to insert a chain of two carbon atoms with a further functionalization under mild conditions. We have studied this new methodology which involves the stepwise formation of a C‐C and a C‐X bond (with
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Kinetic Resolution of Cyclic Tertiary Alcohols with Lipase A from Candida antarctica Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-02 Satoshi Horino, Karla Wagner, Anke Hummel, Kyohei Kanomata, Harald Gröger, Shuji Akai
Enzyme‐catalyzed acylative kinetic resolution (KR) and dynamic kinetic resolution (DKR) of racemic primary and secondary alcohols have been widely reported to produce esters with high enantiomeric purity. In contrast, similar KRs of tertiary alcohols have been reported for only a limited range of substrates and require prolonged reaction times of several days. To gain deeper insight into the substrate
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TBHP: A sustainable alternative for Carbon‐Oxygen Bond Formation Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-02 Jyoti .., Suman Devi, Deepak Wadhwa, Jayant Sindhu, Vikram Kumar
Over past few decades, synthetic chemists are working tirelessly for the development of environmentally benign and economically competent carbon‐oxygen bond formation processes. Various oxidizing reagents and catalysts are being used to serve this purpose. Among all, t‐butyl hydrogen peroxide (TBHP) has emerged as a greener and economically viable oxygen source, radical initiator and precursor of t‐BuO•
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Synthesis of Aza‐Bicyclic Maleimide Skeleton by Addition‐Ring Opening Cascade Reaction of Vinylogous Oxindole Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-01 Qian Liao, Yang Zhang, Jin-Yu Liu, Qing-Song Li, Yu-Ming Huang
An efficient method has been developed to facilitate the addition‐ring opening cascade reaction of vinylogous oxindole, resulting in the synthesis of a variety of aza‐bicyclic maleimide derivatives with high yields and exceptional diastereoselectivities. Furthermore, the product could be effectively and easily transformed into the difluoromethylenecyclohexane skeleton through a dehydrofluorination
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Base‐catalyzed Highly Regioselective Synthesis of Bio‐based Hydroxyurethanes Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-01 Felipe de la Cruz-Martínez, Enrique Francés-Poveda, Michael North, José Antonio Castro-Osma, Agustín Lara-Sánchez
The regioselective synthesis of carbamates from bio‐derived cyclic carbonates and amines by using 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD) as an organocatalyst is reported. This methodology led to the preparation of a wide range of bio‐sourced hydroxyurethanes from furan‐, carvone‐ and limonene‐based scaffolds under solvent‐free and mild reaction conditions. Moreover, a comprehensive analysis of the
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Direct and Stereoselective Protecting‐Group‐Free N‐ADP‐Ribosylation through Traceless Staudinger Ligation Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-01 Rui Hagino, Naoko Komura, Akihiro Imamura, Hideharu Ishida, Hiromune Ando, Hide-Nori Tanaka
Adenine diphosphate (ADP)‐ribosylation catalyzed by bacterial toxins is the addition of an ADP‐ribose moiety to specific amino acid residues in target proteins such as arginine, asparagine, glutamine, and histidine through 1,2‐cis(α)‐glycosidic bond formation. ADP‐ribosylation modifies host cell functions, altering normal cellular processes to facilitate their survival, and replication. Despite the
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N‐Directed defluorinative γ‐C(sp3)−H allylation of sulfamate esters for synthesis of gem‐difluoroalkenes via photoredox catalysis Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-29 Jia-Wen Yang, Meng Li, Guang-Qiang Tan, Feng Liu, Hai Tao Qin
gem‐Difluoroalkenes are unique structural motifs with important applications ranging from drugs to materials. Herein, we report a novel radical‐mediated defluorinative allylation of sulfamate esters with α‐trifluoromethyl alkenes through distal C(sp3)−H functionalization under photoredox conditions. The reaction could readily incorporate various gem‐difluoroalkene motifs into previously unfunctionalized
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Base‐ and Visible‐Light‐Promoted Formation of 3‐Benzyl‐3‐Methoxyisoindolin‐1‐one Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-29 Nathan Martin, Aurélien Moncomble, Lydie Pélinski, Eric Deniau, TILL BOUSQUET
Aryl diazonium salts are versatile compounds known for their reactivity in various transformations. In this study, we explored the arylation of 3‐methylene isoindolinones using aryl diazonium salts. The objective was to develop a method for accessing 3‐benzyl‐3‐methoxyisoindolin‐1‐ones, a class of compounds with diverse biological activities and synthetic importance. Optimization of the reaction conditions
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Bimetallic Ru(II) Complex Catalysed β‐Alkylation of Secondary Alcohols and α‐Alkylation of Ketones: Selective Formation of Saturated Ketones Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-29 Gopal Deshmukh, Ramaswamy Murugavel
Ru(II) bimetallic [(p‐cymene)2(RuCl)2L1]2X (X = BF4 (Cat2); X = PF6 (Cat3)) and monometallic [(p‐cymene)(RuCl)L2]BF4 (Cat4) (where L1 = N,N'‐(3,3',5,5'‐tetraisopropyl‐[1,1'‐biphenyl]‐4,4'‐diyl)bis(1‐(pyridin‐2‐yl)methanimine); L2 = N‐(2,6‐diisopropyl‐phenyl)‐1‐(pyridin‐2‐yl)‐methanimine) catalyse selective synthesis of saturated ketones using β‐alkylation of secondary alcohol or α‐alkylation of ketones
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Advances in Enzymatic Incorporation of Small Fluorine Modules Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-29 Yuqi Lin, Wanqing Xue, Hechen Li, Bingmei Su, Juan Lin, Keyin Ye
Organofluorine compounds find extensive application in the fields of agrochemicals, pharmaceuticals, materials science, and molecular imaging. Introducing fluorine atoms can provide organic compounds with unique physicochemical properties or improve their biological activity. Although significant progress has been made in the chemical synthesis of fluorine‐containing compounds, achieving selective
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Heteroaryl 2‐Sulfonamide Synthesis by SN2 Reaction‐Oxidation Cascade Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-28 Lu Yan, Chaofan Xu
Heteroaryl 2‐sulfonamides are an important structural moiety in drug discovery. However, reports of the efficient synthesis of these scaffolds are rare. Herein we disclose new reaction conditions to synthesize heteroaryl 2‐sulfonamides from disulfanes and amines through an SN2–oxidation cascade. The approach is compatible with a wide variety of heteroaryl and amine substrates and can be conducted on
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Front Cover: Synthesis and Photochemical Characterization of Indolizine Fluorophores Obtained by a Multicomponent Palladium Iodide−Catalyzed Oxidative Aminocarbonylation Approach (Eur. J. Org. Chem. 12/2024) Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-28 Ida Ziccarelli, Roberta Amuso, Raffaella Mancuso, Antonio Maggiore, Giuseppe Lamberti, Paola Vitale, Vincenzo Maiorano, Lucia Veltri, Bartolo Gabriele
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SO2F2‐Mediated Thioesterification of Carboxylic Acids with Thiols Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-27 Guofu Zhang, Huijie Qi, Chenfei Guan, Hui Jin, Ying Zhou, Chengrong Ding
The generation of thioesters through thioesterification of carboxylic acid has significant synthetic value given the easy availability of various carboxylic acids and the extensive application of thioesters. An economical and rapid thioester synthesis approach is still needed. Herein, we achieved thioesterification of carboxylic acids with valuable glycosyl thiol, aromatic and aliphatic thiols mediated