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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
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Palladium Catalyzed Carbonyl Amination of Fluorinated Olefins for Synthesis of α‐CF3‐Acrylamides Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-27 Yang Li, Yu Jing, Yi‐Ran Shi, Hong Li, Min‐Ge Yang, Yong‐Li Kou, Qiang‐Wei Fan
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Dehydrogenative N‐N Coupling and Facile Synthesis of Cobalt Complexes Supported by Tetrazene Based Ligand: Synthesis of Quinolines and Quinazolinones via Activation of Alcohols Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-26 Sheela Kumari, Ankur Maji, Rahul Chauhan, Virendra K. Chaudhary, Tapasya Kush, Mayank Joshi, Angshuman R. Choudhury, Kaushik Ghosh
Herein we first report the unprecedented synthesis of tetrazene‐based cobalt complexes using unusual coupling of amines via dehydrogenation. These cobalt complexes were employed for dehydrogenative coupling reactions to synthesize N‐heterocycles (quinoline, and quinazolinone). Based on control experiments and IR identification of intermediates, we proposed a plausible reaction mechanism. Synthesis
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Recent Advances in the Direct N–C(sp2) Nitrone Synthesis from Oxime Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-25 Kosaku Tanaka
Nitrones are pivotal in organic chemistry, especially for the synthesis of natural and biologically active compounds via 1,3‐dipolar cycloadditions and Kinugasa reactions. Although numerous methods have been reported for the synthesis of nitrones with an sp3 carbon connected to a nitrogen atom, the development of nitrones with an sp2 carbon linkage, including N‐vinyl, N‐aryl, and N‐alkoxycarbonyl nitrones
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Exploring the Reactivity of Melanins as Photocatalysts for Reductive Dehalogenations Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-25 Andrea Capucciati, Valentina Foli, Pasquale Lioniello, Maria Laura Alfieri, Elena Cassera, Daniele Merli, Paola Manini, Davide Ravelli
Four melanin polymers prepared from different precursors (5,6‐dihydroxyindole, 5,6‐dihydroxyindole 2‐carboxylic acid, 1,8‐dihydroxynaphthalene and dopamine) have been adopted as photocatalysts in the reductive dehalogenation of a series of model a‐halogen carbonyl derivatives. The best performing melanin was that obtained from 5,6‐dihydroxyindole 2‐carboxylic acid, which allowed to dehalogenate efficiently
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Commercial transaminases for the asymmetric synthesis of bulky amines. Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-25 Marianne Bore Haarr, Kotchakorn T.sriwong, Elaine O'Reilly
Transaminase‐catalysed asymmetric amination is a valuable transformation for the synthesis of chiral amines. However, its use in synthetic chemistry has been curtailed by a narrow substrate scope and limited information on commercially available catalysts. In this work we have explored the substrate scope of selected commercially available transaminases, focusing on prochiral ketones bearing two bulky
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Polymorphism and White Light Emission of 1‐Bromo‐3,5,7‐triphenyladamantane Compared with 1,3,5,7‐Tetraphenyladamantane Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-25 Saravanan Gowrisankar, Andrey A Fokin, Jonathan Becker, Neeshma Mathew, Jörn Schmedt auf der Günne, Peter Richard Schreiner
Here we report our investigation of 1‐bromo‐3,5,7‐triphenyladamantane (1) and the elucidation of polymorphic crystals (1A and 1B) using single crystal X‐ray diffraction. In the monoclinic crystal system of 1A (P21/n), we observed CH−π interactions, while Br···Br interactions are absent. Conversely, the Br···Br interactions are an apparent factor in the formation of the monoclinic crystal system of
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Synthesis of a Bicyclo[1.1.1]pentane‐Containing Aromatic Lipoxin B4Analogue and Heteroaromatic Congeners Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-23 Benjamin Owen, Patrick Jerome Guiry
Lipoxins are pro‐resolving mediators that play an important role in the resolution phase of the innate inflammatory response. However, because of their chemical and metabolic instability, the design of more stable synthetic analogues of lipoxin A4 and lipoxin B4 is an ongoing area of study. Herein we report the asymmetric synthesis of an aromatic lipoxin B4 analogue containing a conformationally rigid
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Aerobic Photoredox Catalyzed Oxamate Ester Synthesis from Bromodifluoroacetate Esters Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-23 Takuma Tagami, Shintaro Kawamura, Mikiko Sodeoka
Here we report an aerobic photoredox catalysis approach to oxamate ester synthesis using bromodifluoroacetate esters and amines under open‐air conditions. Oxamate ester is an important skeleton found in bioactive molecules and used as a synthetic building block. However, previous synthetic methods require the use of moisture‐ and air‐sensitive precursors and/or harsh conditions, limiting accessible
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Metal‐Free K2S2O8 Mediated Synthesis of 3‐(Substituted)‐2‐Arylisoindolin‐1‐one Derivatives With Cascade C‐N / C‐C Bond Formations Via Radical Cyclization Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-22 Soumitra Rana, Rajiv Karmakar, Uday Shee, Chhanda Mukhopadhyay
A facile technique was demonstrated for the synthesis of 2‐hydroxy‐2‐[N‐(alkyl/aryl/heteroaryl)‐3‐oxoisoindolin‐1‐yl]‐1H‐indene‐1,3(2H)‐diones by using a metal‐ free persulfate‐mediated one pot three‐component reaction. The reaction involved the combination effect of TBAB (PTC) and K2S2O8 with the addition of the amine to phthalaldehyde and 2,2‐dihydroxyindane‐1,3‐dione to generate isoindolin‐1‐one
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Selective Synthesis of Functionalized 3(2H)‐Furanones via Tandem MichaelAddition/Rearrangement/Cyclization Reaction of Aliphatic Alkynones: A Combined Experimental and Theoretical Study Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-22 Sofia Karnakova, Anton Kuzmin, Igor Ushakov, Dmitrii Shabalin
A novel catalyst‐ and solvent‐controlled dimerization of aliphatic alkynones through tandem Michael addition/rearrangement/cyclization sequence has been developed. The elaborated protocol provides a convenient chemo‐, regio‐ and stereoselective access to rare 3(2H)‐furanones decorated with 2‐exo‐methylene and 4‐ethenyl functionalities. A comprehensive density functional theory (DFT) study of possible
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Mechanochemical Assembly of a Nitrile‐Based Directing Group in Arylacetic AcidsUsing the Passerini 3‐CR: Exploration of the Pd(II)‐Catalyzed meta‐C(sp2)‐H Bond olefination Process Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-22 Juvenal García-Uribe, Sebastián Martínez-Flores, Valeri Martínez-Barrita, Luis Angel Polindara-García
The multicomponent assembly of a nitrile‐based directing group in a set of arylacetic acids under solvent‐free mechanochemical conditions using the Passerini 3‐CR and the subsequent Pd(II)‐mediated meta‐C(sp2)‐H bond olefination process has been achieved. The protocol demonstrated that removing the DG under mild conditions from the activated Passerini adducts affords a novel N‐(tert‐butyl)‐2‐(2‐cy
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A ChemoEnzymatic Approach for the Preparation of “Linear‐Shaped” Diaryl Pyrazines as Potential Antiprotozoal Agents Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-22 Ivan Bassanini, Tommaso Braga, Chiara Tognoli, Marta Vanoni, Gaia Mazza, Nicoletta Basilico, Silvia Parapini, Sergio Riva
Nitrogenous heterocyclic rings are present in a wide range of drugs, natural compounds, and fine chemicals and are considered privileged scaffolds in medicinal chemistry. Seeking novel antiprotozoal drugs acting on new targets or by novel mechanisms of action, we focused on a preliminary evaluation of the potential of “linear‐shaped” diaryl pyrazines. To this purpose, a two‐enzyme chemoenzymatic synthesis
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Selective Palladium(II)‐Catalyzed Dimerization of Styrenes and Acrylates in Molten Tetrabutylammonium Acetate as an Ionic Liquid Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-22 Andrea Aloia, Michele Casiello, Angelo Nacci, Antonio Monopoli
: A method for the selective dimerization of styrenes and acrylates has been developed. The reaction is catalyzed by a very low amount of palladium acetate in molten tetrabutylammonium acetate without the need for any additional ligand. The use of this method enabled the coupling of substituted vinyl arenes in reasonable yields to give exclusively the (E,E)‐1,4‐diarylbutadiene motif within 7‐10 h.
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Recent Advances in the Synthesis of Chiral Allenes via Asymmetric 1,4‐Difunctionalization of 1,3‐Enynes Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-22 Sijia Li, Kaiyao Yuan, Guozhu Zhang, Rui Guo
Allenes represent a distinctive class of organic molecules characterized by their unique physical and chemical properties. Among them, chiral allenes play a significant role in modern chemistry. They not only serve as pivotal frameworks for natural products and drug molecules but also are essential building blocks in organic synthesis. Over the years, numerous remarkable and efficient methods have
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Double winding vine‐shaped biphenyl with molecular asymmetry. Synthesis, structure, and properties Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-21 Atsunori Mori, Aruto Maruka, Kohei Tabuchi, Kentaro Okano, Masaki Horie
A biphenyl derivative in which two benzene rings are strapped with two chains is prepared. The synthesized product shows molecular asymmetry, which was confirmed by HPLC analysis with chiral column and named as winding vine‐shaped biphenyl. The synthesis of such vine shaped molecule was performed by ring‐closing metathesis or alternatively by annulation with nosylated ethylenediamine. The structure
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Molecular Networking‐Guided Discovery of Kyonggic Acids in Massilia spp. Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-21 Till Steinmetz, Anton Lindig, Stephan Lütz, Markus Nett
In recent years, bacteria of the genus Massilia have been identified as promising sources of bioactive natural products. In this study, we used mass spectrometry (MS)‐based molecular networking for the first comprehensive analysis of the secondary metabolome of these microorganisms. Annotation of the detected metabolite clusters with a mass fragmentation database revealed several compounds not previously
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[N–I–N] Type Halogen Bonding: Structure, Synthesis and Applications Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-21 Tianhao Wang, Pengyao Xing
Halogen bond has received widespread attention in recent years due to the vast applications in supramolecular chemistry, sensing and crystal engineering. In contrast to the normal halogen bonds, [N–I–N] type halogen bond exhibits enhanced strength and solvent resistance capabilities. It adopts a bonding geometry of the three‐center four‐electron bond, where the nitrogen can be a neutral, positive,
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Visible‐Light‐Induced Metal‐Free Three‐Component Amidoheteroarylation of Alkenes to Synthesize β‐(Hetero)arylethylamines Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-21 Qiange Feng, He Wang, Yang Liu, Lin Wei, Jing Sun, Xin Wang, Ran Sun, Yujia Wang, Lei Li
Herein, visible‐light‐induced metal‐free three‐component amidoheteroarylation of alkenes with quinoxalin‐2(1H)‐ones and N‐sulfonylaminopyridinium salts is developed. This protocol involves a radical relay process in which the N‐centered radicals undergo chemoselective addition to alkenes to form an alkyl radical that selectively combines with heteroarenes, leading to the formation of C−C and C−N bonds
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Uranyl‐Organic Framework as Hydrogen Atom Transfer Catalyst for Visible‐Light‐Driven Heterogeneous Hydroacylation of Azodicarboxylates Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-21 Lei Chen, Ke-Xin Tan, Zhi-Jian Zheng, Xiao-Ling Lin, Bang-Ming Ming, Zhi-Bin Zhang, Guoping Yang
The direct C−H to C−N bond conversion at room temperature using heterogeneous visible‐light catalysts is both interesting and challenging. Herein, we disclosed visible‐light‐promoted hydroacylation of azodicarboxylates using uranyl‐organic framework [UO2(OH)(cpt)]n (Ucpt, Hcpt = 4‐(4'‐carboxyphenyl)‐1,2,4‐triazole) as an efficient heterogeneous hydrogen atom transfer photocatalyst. In this procedure
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Phosphine‐Catalyzed 1,6‐Addition and Tandem Addition/Self‐Aldol Condensation Reactions of para‐Quinone Methides with Thiols Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-20 Yuan Zhong, Guichen Li, Dan Zhang, Yuxuan Xie, Long Hao, Zhengjun Cai, Xin Wang
Phosphine‐catalyzed chemodivergent reactions of para‐quinone methides (p‐QMs) affording a wide variety of diarylmethyl thioether derivatives have been reported. In the transformation presented in this work, P(4‐FC6H4)3 catalyzed the direct 1,6‐addition of p‐QMs with thiols, whereas P(4‐MeC6H4)3 promoted the tandem addition/self‐aldol condensation reactions of p‐QMs with 1,4‐dithiane‐2,5‐diol. Moreover
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Halogen Promoted Desulfurative Cleavage of Cyclopropylmethyl Thioethers and Amination of the Formed Cyclopropylcarbinyl Cations Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-20 Pablo Marín-Díaz, Clara Martínez-Núñez, Roberto Sanz, Samuel Suarez Pantiga
Cyclopropylmethyl sulfides react with N‐fluorosulfonimide (NFSI) or molecular iodine, enabling C–S cleavage to generate cyclopropylcarbinyl cations, which evolve through cyclopropane ring‐opening reactions into homoallyl cations suitable to react with nucleophiles present in the reaction media. This desulfurative cleavage of cyclopropylmethyl thioethers under non‐acidic conditions facilitates homoallylation
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Visible‐Light Induced Trifluoromethylation/Cyclization of Unactivated Alkene‐Bound Quinazolinones Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-19 Luqian Zou, Hengyuan Zhao, Xianming Wang, Jun Dong, Chungang Yang, Weiqing Sun, Jianbin Xu, Baomin Fan
Herein, we reported a selective, mild method for the visible light‐photocatalyzed trifluoromethylation and cyclization of unactivated tethered alkenes to provide tri‐ and tetracyclic quinazolinones. Trifluoroacetic acid and anhydride are inexpensive and readily available reagents for the process which proceeds without the addition of a strong oxidant. Broad substrate scope and the formation of 5‐ and
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Hexafluoroisopropanol Catalyzed Ring‐Opening‐Cyclization of Donor−Acceptor Cyclopropanes with Primary Amines Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-19 Srinivasarao Yaragorla, Rajeshwari Tangellapally, Doma Arun
We reveal here a metal‐free, ring‐opening‐cyclization of donor‐acceptor cyclopropanes with primary amines to synthesize functionalized dihydropyrroles. This protocol avoids inert conditions and solvents promoted by hexafluoroisopropanol (HFIP). The reaction is quite general with aryl, alkyl, and alicyclic amines. A good number of cyclopropanes bearing keto groups reacted excellently to produce the
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Cu(III)‐CF3 Compound‐Activated DMSO: An Efficient Oxidizing Reagent to Convert Alcohols to Ketones Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-19 Yi-Feng Hou, Song-Lin Zhang
In this study high‐valent Cu(III) trifluoromethyl compounds in combination with DMSO is shown to be an efficient and mild oxidizing system for the conversion of alcohols to ketones (aldehydes as well). Trifluoromethoxylated sulfonium species is proposed to be initially formed that engages in crucial steps of alkoxy replacement at sulfonium center and deprotonative collapse of the resulting alkoxysulfonium
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Ligand‐Free Cu(0) Catalyzed C–S Cross‐Coupling Ullmann‐type Reaction: S‐Arylation of 5,4‐Disubstituted‐2,4‐dihydro‐3H‐1,2,4‐triazole‐3‐thiones. Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-19 Artyom Petrosyan, Armen Ayvazyan, Tariel Ghochikyan, Armen Galstyan
Studied the S‐arylation of 5,4‐disubstituted‐2,4‐dihydro‐3H‐1,2,4‐triazole‐3‐thiones under ligand‐free Cu(0) catalyzed Ullmann‐type reaction conditions. Optimum reaction conditions and the effect of substituents in the arylating agent on the course of the reaction were revealed. The presence of EWG in aryl halides allows the reaction to be carried out without a catalyst, in particular, the presence
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Adventures in the Chemistry of Multicomponent and Domino Reactions Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-19 Peter Langer
The present personalized account summarizes various cyclization reactions, including multicomponent and domino processes, which are directed towards the synthesis of complex heterocyclic products. Reactions include, for example, various domino Knoevenagel /cyclization reactions, formal [3+3] cyclizations of pyridinium salts and of thioxindoles with fluoroaroyl chlorides, cyclizations of heterocyclic
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Photochemical Trifluoromethylative Difunctionalization of Styrenes and Phenylacetylenes via a Catalytic EDA Platform Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-19 Seshadri Reddy Nasireddy, Ganesh Chandra Upreti, Anand Singh
Herein we report a visible‐light‐induced trifluoromethylative difunctionalization of styrenes and phenylacetylenes using trifluoromethyl thianthrenium triflate (TT‐CF3+OTf−). The transformation was enabled by the discovery of a photoactive catalytic EDA complex formed between carbazolyl dithiocarbamate and TT‐CF3+OTf−. This three‐component reactivity platform establishes a new paradigm for TT‐CF3+OTf−
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A New Strategy for the Synthesis of (+)‐Crambescin B Decarboxylate Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-03-19 Yuki Yonekura, Masahide Konno, Taku Ozaki, Atsuo Nakazaki
Crambescin B decarboxylate is an inhibitor of voltage‐gated sodium‐channel and a potential biochemical tool. Herein, we report the asymmetric total synthesis of crambescin B decarboxylate using a new synthetic strategy. The key aspects of this new protocol include: 1) the use of an optically pure epoxide, synthesized by the Jacobsen hydrolytic kinetic resolution, as the starting material for guanidino‐aziridine
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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 : 2024-03-18 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 : 2024-03-18 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 : 2024-03-16 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 : 2024-03-08 Marine Pinaud, Erwan Le Gall, Marc Presset
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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
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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
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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
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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 : 2024-03-05 Hao-Yuan Li, Xiaoying Niu, Xiu-Long Yang
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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