Artikel[2+2] Cycloadditions of Methylene exo‐Glycals: Synthesis of Glycopyranosylidene‐Spiro‐Azetidine‐2‐ones (β‐Lactams) and Cyclobutanonesvon János József et al. · 21.03.2023 New anomeric spiro-β-lactam and spiro-cyclobutanone derivatives were synthesized by [2+2] cycloadditions of methylene exo-glycals with chlorosulfonyl isocyanate and dichloroketene. The reactions were studied in detail, investigating the effect of ca...
ArtikelO‐Acylative Vinylation of Cyclodextrin‐Based [3]Rotaxane Towards Rotaxane Crosslinkersvon Yosuke Akae et al. · 21.03.2023 Random acylation of cyclodextrin (CD) was revealed to highly depend on the steric hindrance of the reagent. Based on this phenomenon, the facile synthesis of a [3]rotaxane crosslinker was implemented via random methacrylation without any demanding s...
ArtikelHalogen Dance on 2‐Iodobenzofuran and 2‐Iodobenzothiophene and Related Reactionsvon Loubna Elmir et al. · 21.03.2023 New derivatives of benzofuran and benzothiophene were synthesized by halogen dance from the 2-iodinated precursors. In addition, our efforts to deprotometallate 2-substituted (SiR3, CH(OH)R) benzofurans and benzothiophenes at the 7-position are repo...
ArtikelCatalytic Asymmetric Friedel–Crafts Alkylation of Indole via In Situ Generated Indol‐2‐onevon Yuanai Fei et al. · 21.03.2023 An asymmetric Friedel–Crafts alkylation of indole derivatives with in situ generated indol-2-ones from functionalized 3-bromooxinidoles to construct 3-substituted 3’-indolyloxindole skeleton catalyzed by chiral N,N’-dioxide/Ni(BF4)2 has been develop...
ArtikelMetal‐Free, Photoredox‐Catalyzed Synthesis of Quinazolin‐4(3H)‐ones and Benzo[4,5]imidazo[1,2‐c]quinazolines Using Trialkylamines as Alkyl Synthonvon Ajithkumar Arumugam et al. · 21.03.2023 A metal-free, visible-light photocatalytic approach for the construction of 2-alkyl substituted quinazolin-4(3H)-ones and benzo[4,5]imidazo[1,2-c]quinazolines using trialkylamines as carbon synthons has been developed. Some of the notable features o...
ArtikelConcise Total Synthesis of rac‐Betuphenone Fvon Nguyen Ngoc et al. · 21.03.2023 Betuphenone F, a natural product isolated from the bark of Betula alnoides Ham. ex D. Don, has the potential to be a new-generation anti-cancer agents based on anti-austerity. We succeeded in constructing the 2-oxabicyclo[3.3.1]nonane skeleton, a st...
ArtikelNegishi Cross‐Coupling in the Preparation of Benzyl Substituted Pyrrolo[2,3‐d]pyrimidine Based CSF1R Inhibitorsvon Thomas I. et al. · 21.03.2023 CSF1R is a protein kinase emerging as an attractive target with medicinal chemistry. Guided by molecular docking a series of pyrrolopyrimidine inhibitor candidates have been synthesis using Negishi and Suzuki–Miyaura cross-coupling in the key steps....
ArtikelMultidynamic Crystalline Molecular Rotors Comprising an N‐Heterocyclic Carbene Binuclear Au(I) Complex Bearing Multiple Rotatorsvon Mingoo Jin et al. · 21.03.2023 Herein, we report novel multi-rotational solid-state dynamics utilizing a crystalline molecular rotor bearing multicomponent rotators encapsulated by a concave-shaped NHC Au(I) complex. The motion of the central pyrazine and neighboring THF molecule...
ArtikelHemin‐Promoted Direct C−H Thiolation in the Synthesis of Diaryl Sulfidesvon Bao Li et al. · 21.03.2023 A new method for direct preparation of diphenyl sulfides using P-toluenesulfonyl chloride as an effective thiophenyl radical precursor with assistance from Hemin. Various substituted anisoles and benzenesulfonyl chlorides are well tolerated. Gram sc...
ArtikelDiscovery of New Cytotoxic Aplaminone Derivatives from the Sea Hare Aplysia kurodai and Elucidation of Their Accumulation from Local Sea Algae through the Food Chainvon Yusuke Hioki et al. · 21.03.2023 Six new cytotoxic aplaminone derivatives 3–8 were discovered from the herbivorous marine mollusk Aplysia kurodai. A comprehensive LC–MS/MS analysis of the extracts of sea algae distributing in the habitats of A. kurodai revealed that aplaminones cou...
ArtikelElectrochemically Generated Copper(I)‐Catalyzed Click Chemistry: Triazole Synthesis and Insights into Their Photophysical Propertiesvon Murugan Krishnan et al. · 21.03.2023 Catalytic azide-alkyne cycloaddition via electrochemically generated cuprous species leading to 1,2,3-triazoles in good yield and regioselectivity was accomplished. Selected triazoles were applied for the spectrophotometric detection of transition m...
ArtikelFront Cover: Katritzky Salts for the Synthesis of Unnatural Amino Acids and Late‐Stage Functionalization of Peptides (Eur. J. Org. Chem. 12/2023)von Ali Munaim et al. · 21.03.2023 The Front Cover shows chalkboard drawings of recent advances in the use of Katritzky salts as intermediates for the synthesis of unnatural amino acids, late-stage functionalization of peptides, and macrocyclization. Thanks to the progress made in de...
ArtikelCover Feature: O‐Acylative Vinylation of Cyclodextrin‐Based [3]Rotaxane Towards Rotaxane Crosslinkers (Eur. J. Org. Chem. 12/2023)von Yosuke Akae et al. · 21.03.2023 The Cover Feature illustrates the acylation reaction of cyclodextrin (CD)-based [3]rotaxane. In this reaction system, one [3]rotaxane has 36 hydroxyl groups on two CD units, and excess of methacryl anhydride was added, as shown on the background. Ho...
ArtikelKatritzky Salts for the Synthesis of Unnatural Amino Acids and Late‐Stage Functionalization of Peptidesvon Ali Munaim et al. · 21.03.2023 In the last few years, Katritzky salts emerged as a potential tool for the synthesis of unnatural amino acids, and late-stage functionalization of peptides. In this review, we summarized the applications of deaminative functionalization in the pepti...
ArtikelTransition‐Metal‐Free Radical Borylation Reactionsvon Zhi‐Hao Shang et al. · 21.03.2023 This review provides an overview of recent advances in the discovery, development, and mechanistic studies of transition-metal-free radical borylation processes. Abstract Organoboron compounds are versatile synthons in synthetic chemistry, materia...
ArtikelSelective Radical Transformations with Aryldiazonium Saltsvon Edson Leonardo et al. · 21.03.2023 Since 1858, aryldiazonium salts have been inspiring chemists to use them as dye precursors and as substrates for ionic or radicalar transformations. The latter is experiencing a renaissance among the reliable methodologies in chemical synthesis due ...
ArtikelChemistry and Applications of Functionalized 2,4‐Thiazolidinedionesvon Ayman et al. · 29.03.2023Thiazolidinedione (TZD) is one of the privileged heterocyclic rings and has shown many biological applications in medicinal chemistry and drug discovery. The manuscript covers the synthetic approaches of TZD and its derivatives, different synthetic t...
ArtikelSubstrate‐Controlled Hydrogenation of Flavanones: Selective Synthesis of 2′‐Hydroxy‐1,3‐Diarylpropanes and Flavansvon Martín Soto et al. · 29.03.2023 Herein, a new substrate-controlled hydrogenation of flavanones to selectively obtain 2′-hydroxy-1,3-diarylpropanes or flavans depending on the substitution of the flavanone moiety is described. Thus, hydrogenation of non-fluorinated flavanones provi...
ArtikelDesign and Synthesis of Linearly Fused Triquinanes via Tandem‐Metathesis: Access to Basic Core of Cucumin, Capnellene, Chondrosterin, and Xeromphalinonevon Sambasivarao Kotha et al. · 29.03.2023Herein, a short synthetic approach to linearly fused tricyclic enone 1 and cis-anti-cis type hydroxy-triquinane 2 has been described in an efficient manner by employing tandem-metathesis as a key step. The triquinane-based enone 1 is prepared by a Ba...
ArtikelSelf‐Promoted N‐Glycosylation: Extended Substrate Scope and Substituent Effectsvon Benedicte Rønne et al. · 28.03.2023 Amino acid sidechains have been functionalized and glycosylated without the aid of catalysts or additives. Disarmed glycosyl donors were found to react efficiently and excess glycosyl acceptor as well as trichloroacetamide could effectively be remov...
ArtikelWhite Light/NIS‐Promoted Aminoselenylation of Alkenes by Using N‐Tosylhydrazonesvon Xianlie Chen et al. · 28.03.2023 A three component reaction of alkenes, N-tosylhydrazones, and diorganyl diselenides for the synthesis of organylselenylethyl sulfonylhydrazones is disclosed, in which 42 products were synthesised in moderate to excellent yields (51 %–85 %). In addit...
ArtikelPd/Ni Co‐catalyzed Selective Cross‐Coupling of Aryl Bromides and Aryl Fluorosulfonates at Room Temperaturevon Guofu Zhang et al. · 28.03.2023 This work reports a method for the synthesis of biaryls using inexpensive aryl fluorosulfonates coupled with electrophilic reagents, which enhances the selectivity of the cross-coupling products by palladium and nickel cooperative catalysis. This re...
ArtikelDesign and Synthesis of Exocyclic Cyclitol Aziridines as Potential Mechanism‐Based Glycosidase Inactivatorsvon Tim et al. · 27.03.2023Cyclophellitol aziridines have found wide application as mechanism-based, covalent and irreversible inhibitors of retaining glycosidases. These compounds, like their parent compound, cyclophellitol (a natural product retaining β-glucosidase inactivat...
ArtikelMetal‐ and Catalyst‐Free Synthesis of 2‐Substituted‐Phthalimides Using 2‐(Arenesulfonyl)Phthalimide as Key Reagentsvon Abdalrahman Khalifa et al. · 27.03.2023Phthalimide derivatives are an important tool in medicinal chemistry, thus several phthalimidation methodologies have been developed. Here, we report a facile, metal-free, and catalyst-free method for the preparation of N-phthalimides in good to exce...
ArtikelPyrazolo[1,5‐a]pyrimidine‐Dioxaborinine Hybrid Dyes: Synthesis and Substituent Effect in the Photophysical Propertiesvon Alexis Tigreros et al. · 25.03.2023 A novel family of hybrid fluorophores based on the pyrazolo[1,5-a]pyrimidine-dioxaborinine (PP-DB) system is provided by constructing the dioxaborinine moiety on the fused ring in a one-pot manner. Abstract A novel family of pyrazolo[1,5-a]pyrimid...
ArtikelMetal‐Free and Mild Synthesis of 2,4‐Diarylquinolinesvon Shanshan Li et al. · 25.03.2023 In this paper, a practical and efficient one-pot, non-transition metal, regioselective route has been designed for the direct synthesis of 2,4-diarylquinolines containing diverse functional groups of different electronic and steric nature from 2-(1-...
ArtikelA Historical Review of the Total Synthesis of Natural Products Developed in Portugalvon Duarte B. et al. · 25.03.2023 This review summarizes the strategies for the natural product synthesis that were developed in Portugal in the past five decades, including alkaloids, cyclitols, phenylpropanoic acids, γ-butyrolactones, fatty alcohols, xanthones and nucleosides. A...
ArtikelVisible‐Light‐Promoted Reaction of N‐Hydroxyphthalimide Esters with Vinyl Boronic Pinacol Estervon Petros L. et al. · 25.03.2023 A light-driven protocol to access alkyl boronic acid pinacol esters from vinyl boronate using N-hydroxyphthalimide esters as the alkyl generator was developed. A good substrate scope was examined, demonstrating good to high yields and excellent func...
ArtikelIron‐Catalyzed Trifluoromethylation of Indole‐Tethered Alkene Enables Synthesis of CF3‐Containing Spiroindolenines and Tetrahydrocarbazolesvon Yilin Zhao et al. · 24.03.2023A novel iron-catalyzed trifluoromethylation of indole-tethered alkene with Togni’s reagent to construct CF3-containing spiro[indole-3,3’-pyrrolidine] and tetrahydrocarbazole derivatives under mild and convenient conditions has been disclosed. The mec...
ArtikelC2‐Cyanomethyl (CNMe) Ether‐Protected Glycosyl Trichloroacetimidate Donors for Stereoselective β‐O‐Glycosylationsvon Mosidur Rahaman et al. · 24.03.2023 Cyanomethyl (CNMe) ether group has been reported as a stereodirecting C2-protecting group on glycosyl trichloroacetimidate donors. The synthesized donors were activated by TMSOTf catalyst to obtain the β-O-glycosides in excellent stereoselectivities...
ArtikelEnantioselective Desymmetrization of Curcumins with 3‐Olefinic Oxindoles for the Synthesis of Spirocyclohexanoneoxindolesvon Chenikkayala Siva et al. · 24.03.2023 Spiro-oxindoles containing three contiguous chiral centers were synthesized with excellent diastereo- and enantioselectivities via cascade double Michael reactions of curcumins with 3-alkylideneoxindole carboxylates. The selectivities are supported ...
ArtikelVisible‐Light‐Induced Photocatalytic C3‐Trifluoroethylation of Quinoxalin‐2‐(1H)‐onesvon Jian Liu et al. · 24.03.2023 A visible-light-induced C3-trifluoroethylation of quinoxalin-2-(1H)-ones has been developed using an inexpensive organic dye as a photocatalyst and commercially available 1,1,1-trifluoro-2-iodoethane as a trifluoroethyl radical source. This reaction...
ArtikelStereoselective Domino Semipinacol‐Schmidt Reaction: Diastereoselective Synthesis of 7 a‐epi‐(+)‐Lepadiformine C and Formal Synthesis of 7 a‐epi‐(−)‐Lepadiformine Avon Manohar Puppala et al. · 24.03.2023 A TiCl4 Lewis acid-mediated domino semi-pinacol-Schmidt reaction-based approach has been developed for the diastereoselective synthesis of 7 a epi-lepadiformine C (+)-7 and azatricyclic core of 7 a epi-lepadiformine A (+)-8 a. Abstract A concise a...
ArtikelCobalt‐Promoted Transfer Hydrogenation of Azaaryl Ketones by Using Formate as the Hydrogen Sourcevon Rurong Yu et al. · 24.03.2023 A cobalt-catalyzed transfer hydrogenation of azaaryl ketones using formate as hydrogen source was developed and a possible reaction mechanism is proposed. Abstract A novel cobalt-catalyzed reduction of 2-pyridyl ketones and related heteroaryl comp...
ArtikelPhI(OAc)2/I2‐Mediated Decarboxylative C4‐Amination of Coumarin‐3‐Carboxylic Acids via Csp2−H Dehydrogenative C−N Cross‐Coupling under Ambient Conditionsvon Anindita Bhowmick et al. · 24.03.2023 PIDA/I2-mediated decarboxylative C4-amination of coumarin-3-carboxylic acids was achieved via direct Csp2−H dehydrogenative C−N cross-coupling with secondary amines under ambient conditions. Abstract An efficient and straightforward protocol for a...
ArtikelPhotoinduced Metal‐Free Decarboxylative Transformations: Rapid Access to Amines, Alkyl Halides, and Olefinsvon Jia‐jing Luo et al. · 23.03.2023 Herein, we described a versatile photocatalytic strategy for the decarboxylative transformations of redox-active esters (RAE) to a variety of alkyl halides, amines, and olefins in the presence of nBu4NI in a single-step. It is a straightforward meth...
ArtikelReactions in Endohedral Functionalized Cagesvon Matthias Otte · 23.03.2023 Endohedral-functionalized cage compounds play an increasing role in cage chemistry. Here, the recent developments of reactions that are mediated or catalyzed by such endohedral-functionalized cages is reviewed. The article is structured according to...
ArtikelPyridine Adducts of Tricyano‐ and Dicyanoboranesvon Jarno Riefer et al. · 23.03.2023 Efficient syntheses for pyridine and 4-cyanopyridine adducts of the strong Lewis acids BH(CN)2, B(CN)3, and BF(CN)2 starting from readily available hydridoborates are described. The different Lewis acidities of the three boranes have been assessed b...
ArtikelOxovanadium(V)‐Catalyzed Deoxygenative Coupling Reaction of Alcohols with Trimethylsilyl Enol Ethers in the Presence of MS3Avon Takanari Matsutani et al. · 23.03.2023 The deoxygenative coupling reaction of allyl alcohols with trimethylsilyl enol ethers was performed by using a commercially available oxovanadium(V) catalyst, providing γ,δ-unsaturated carbonyl compounds in one-step. This catalytic system could be a...
ArtikelKI‐Mediated Chlorine Gas‐Free Synthesis of 3,3‐Dichloro‐2‐oxindole Derivativesvon Xuejian Li et al. · 23.03.2023 An efficient KI-mediated chloro-oxidation of indoles was developed, using KCl/NaCl as the chlorine source and oxone as oxidant, which affording various functionalized 3,3-dichloro-2-oxindoles in moderate to excellent yields. This chlorine gas-free p...
ArtikelConstruction of C2‐Spirocyclopropyl‐Indolin‐3‐Ones through Base‐Promoted [2+1] Annulation Reaction of Indolin‐3‐ones with Bromosulfonium Saltsvon Mao Zhang et al. · 23.03.2023 A simple and efficient base-promoted [2+1] annulation reaction has been developed for the synthesis of the structural diversity C2-spirocyclopropyl-indolin-3-ones. This [2+1] annulation process using simple and easily prepared nucleophilic indolin-3...
ArtikelVisible Light Promoted Iron‐Catalyzed One‐Pot Synthesis of 2‐Arylimino‐2H‐Chromenes from 2‐Hydroxybenzyl Alcohols and β‐ Ketothioamides at Room Temperaturevon Mohd Waheed et al. · 23.03.2023 An efficient, environmentally benign and one-pot approach for the synthesis of 2-arylimino-2H-chromenes from 2-hydroxybenzyl alcohols and β-ketothioamides at room temperature under visible light has been developed. The reported reaction conditions w...
ArtikelHighly Selective and Practical Iron‐Catalyzed Formal Hydrogenation of Epoxides to Primary Alcohols Using Formic Acidvon Yi‐Xuan Yao et al. · 23.03.2023 Highly selective and efficient synthesis of primary alcohols from epoxides could be achieved under mild conditions by iron catalysis, this process used formic acid as hydrogen source and was suitable for both alkyl- and aryl-substituted epoxides. ...
ArtikelSynthesis of Diastereomeric 8‐Fluoro‐ABC‐Steroid Building Blocksvon Michael Essers et al. · 22.03.2023An eight-steps linear sequence for the preparation of two diastereomers of an 8-fluoro-ABC-steroid building block was developed. Key step was an intramolecular Diels-Alder reaction of an intermediate o-quinodimethane formed from a benzocyclobutene su...
ArtikelPhotoacidity of Indolinospirobenzopyrans in Watervon Cesare Berton et al. · 20.03.2023 Indolinospirobenzopyrans in their open protonated form constitute the archetype of “metastable-state photoacids”, as they can release protons persistently and reversibly following visible light absorption. In this Review, we survey their wide-spread...
ArtikelTotal Synthesis of (‐)‐HM‐3 and (‐)‐HM‐4 using an Asymmetric Gold‐Catalyzed [3,3]‐Sigmatropic Rearrangement of Sulfoniumvon Weiping Zhou et al. · 20.03.2023The asymmetric total synthesis of two sesquiterpenoids, (-)-HM-3 and (-)-HM-4, isolated from phytopathogenic fungus has been developed using as key step a gold-catalyzed [3,3]-sigmatropic rearrangement of sulfonium. During this transformation, an exc...
ArtikelMetal‐Free, Light‐Mediated, Site‐Specific, Radical C6−H Alkylation of Purines with Alcohols Intervened by Oxalates without Catalystsvon Gang Liu et al. · 20.03.2023 The Cover Feature shows a radical deoxyfunctionalization strategy for C6−H alkylation of purines with alcohols. The cover image was inspired by a tenth ring in archery, which represents the high C6-regioselectivity of the reaction with the help of o...
ArtikelSynthesis, Structural Characterization, and Reductive Cleavage of an Oxygen‐Containing Naphthyl Macrocyclevon Zheng Zhou et al. · 20.03.2023 A naphthyl-ether based macrocycle suffers multiple C−O cleavages under chemical reduction. The structures of the macrocycle and the resulting negatively charged fragment are analyzed in detail including single-crystal X-ray diffraction studies. Ab...
ArtikelEnantioselective Synthesis of [b]‐Annulated Azepane Scaffoldsvon Enno Aeissen et al. · 20.03.2023 Optically active α-allyl-β-oxoesters are submitted to olefin cross metathesis and subsequent exhaustive hydrogenation and reductive amination to furnish [b]-annulated azepane derivatives. Abstract Cyclopenta-, benzo-, and cyclohepta[b]-annulated a...
ArtikelAcidic DESs as Active Media for a Sustainable Synthesis of Biindoles Starting from 2,2’‐Diaminotolanes and Aldehydesvon Elisa Brambilla et al. · 20.03.2023We describe an alternative and more sustainable method for the synthesis of 2,2′-disubstituted 3,3′‑biindoles starting from 2,2’-diaminotolanes and (hetero)arylaldehydes. The key feature of the approach is the use of an acidic DES able to exploit a d...
ArtikelChiral Amine Catalyzed Reductive Aldol/Reductive Michael Addition Cascade Towards Enantioselective Synthesis of Benzannulated Diquinanesvon Abhisek Midya et al. · 18.03.2023 Chiral amine catalyzed intramolecular reductive Michael addition cascade to a keto-bis-enone is reported. Enantio- (up to 99 % ee) and diastereoselective benzannulated diquinanes were obtained with three consecutive stereocenters, includes an all-ca...
ArtikelPolystyrene‐Supported Aminocatalyst Derived from Diarylprolinol for Asymmetric α‐Amination of Aldehydesvon Rohtash Kumar et al. · 17.03.2023A new class of polystyrene-supported aminocatalysts with a triazole linker from diphenyl prolinol is achieved. Their catalytic activity is tested in the asymmetric α-amination of aldehydes. The substrate scope of this catalysis is studied under the o...
ArtikelElectrochemical Borylation of Electron‐Deficient Alkenes and Allenoatesvon Maude Aelterman et al. · 17.03.2023 The electrochemical borylation of electron-deficient alkenes and allenoates is described. In an undivided cell under galvanostatic conditions, a panel of Michael acceptors and allenoates was readily reacted. The reaction was efficient and the produc...
ArtikelSynthesis of Phosphate Esters by Using Diphenyl Ditelluride as Organocatalystvon Helen A. et al. · 17.03.2023 This work demonstrates an approach to prepare phosphate esters by a dehydrogenative phosphorylation reaction between functionalized naphthols and H-phosphonates using diphenyl ditelluride as an organocatalyst and sonochemistry as an alternative ener...
ArtikelRegioselective Alkynylation of Allylic Phosphates with Alkynyl Copper Reagentsvon Shunki Mamada et al. · 17.03.2023 We developed a regioselective alkynylation of allylic phosphates with alkynyl copper reagents. The reaction gave 1,4-enynes independent of steric hindrance or electronic effects of the substrate or nucleophile. Then, we efficiently synthesized inter...
ArtikelA Photochemical Protocol for the Synthesis of Weinreb and Morpholine Amides from Carboxylic Acidsvon Asimina Bourboula et al. · 16.03.2023 A photochemical protocol for the synthesis of Weinreb amides and morpholine amides from carboxylic acids is presented. Various carboxylic acids were directly coupled to N,O-dimethylhydroxylamine and morpholine, upon irradiation with either LED 370 n...
ArtikelSynthesis of Dibenzo[b,e]azepin‐6(11H)‐ones via a Sequential Ugi‐4CR and Surfur Ylide‐Mediated Rearrangement Reactionvon Han‐Han Kong et al. · 16.03.2023 A surfur ylide-mediated rearrangement reaction of a functionalized Ugi adduct produced polysubstituted dibenzo[b,e]azepin-6(11H)-ones in good overall yields under mild one-pot reaction condition. Abstract A new one-pot preparation of dibenzo[b,e]a...
ArtikelHighly Fluorescent 2‐Aminopurine Derivatives: synthesis, photophysical characterization, and preliminary cytotoxicity evaluationvon Jorge et al. · 15.03.2023New fluorescent nucleobase analogues (FBAs) are emerging as extraordinarily useful tools for DNA labelling technologies. The highly fluorescent adenine analogue 2‑aminopurine (2AP) is still the most used within the few hundreds of newly FBAs synthesi...
ArtikelSynthesis and Reactivity of Dithienopyrazines von Franziska Kreuzer et al. · 14.03.2023 The efficient preparation and investigation of so far unknown heterotriacenes, basic anti- and syn-dithienopyrazine 5 and 6 is reported. The comparison of the two isomers with respect to electronic properties and follow-up reactions gives insights i...
ArtikelThe Oxidation of Organo‐Boron Compounds Using Electrochemically Generated Peroxodicarbonatevon Philipp et al. · 14.03.2023Peroxodicarbonate represents a green and largely underexplored oxidizer generated electrochemically from aqueous carbonate solutions. Through state-of-the-art electrolyzer technology, highly concentrated solutions have now become accessible. These we...
Artikelβ‐N‐Heterocyclic Cyclobutane Carboximides: Synthesis Via a Tandem Base‐Catalyzed Amidation/aza‐Michael Addition Protocol and Facile Transformationsvon Stefano Barranco et al. · 13.03.2023A stereoselective one-pot double derivatization of cyclobutene-1-carboxylic acid via a mild organic base catalyzed ami-dation/aza-Michael addition of benzo[d]oxazol-2(3H)-ones has been developed. This unprecedented tandem reaction provides access to ...
ArtikelThiocyanation of Allylic Alcohols Promoted by Trifluoroacetic Acidvon Wen Xia et al. · 13.03.2023A rapid and efficient acid-promoted strategy to access allylic thiocyanates using allylic alcohols as substrates and easily available NH4SCN as the thiocyanate source is presented under metal- and oxidant-free conditions. Through screening kinds of a...
ArtikelCopper‐Catalyzed 1,4‐Addition of a Silicon Nucleophile to Azadienesvon wen-dao chu et al. · 13.03.2023The first copper-catalyzed 1,4-addition of a silicon nucleophile to azadienes is developed. This method facilely provided a wide variety of dibenzylic silane derivatives in good to excellent yields. The important practical features are the use of a c...
ArtikelSynthetic Studies Concerned with the Proposed Structure of Ribisin F, a Compound with Nerve Growth Factor Potentiating Activity Isolated from the Medicinal Fungus Phellinus ribisvon Yuqi Zhang et al. · 10.03.2023 The synthesis, from quinic acid, of the enantiomer of the structure assigned to the title natural product has been accomplished but the derived spectral data do not match those reported for ribisin F. A related synthesis of its C3 epimer suggests th...
ArtikelReactivity Tuning of Metal‐Free Artificial Photoenzymes through Binding Site Specific Bioconjugationvon Thomas Kuckhoff et al. · 10.03.2023 A metal-free artificial photoenzyme was designed based on the human steroid carrier protein (SCP-2L), which possesses a hydrophobic tunnel and facilitates substrate binding. Three variants of SCP-2L were bioconjugated with a photocatalytic moiety an...
ArtikelFacile One‐Step Oxidation of N‐Boc‐Protected Diarylhydrazines to Diaryldiazenes with (Diacetoxyiodo)benzene under Mild Conditionsvon Jakub Orvoš et al. · 10.03.2023 Simple, rapid one-step oxidation of shelf-stable N-Boc- and N,N'-bis-Boc-diarylhydrazines with (diacetoxyiodo)benzene provides unsymmetrical diaryldiazenes, arylazopyridines and tris(arylazo)benzenes in good to excellent yields. The method allows fa...
ArtikelIntroducing the DCO‐SCI Prize and Medal Winners 2020 and 2021von Maria Valeria · 09.03.2023 The Division of Organic Chemistry of the Società Chimica Italiana (DCO-SCI) and the European Journal of Organic Chemistry celebrate together, for the first time, the awardees of the Prizes and Medals of the Division 2020 and 2021. Guest Editor Prof....
ArtikelRuthenium‐Catalyzed Direct Reductive Amination of Carbonyl Compounds for the Synthesis of Amines: An Overviewvon Jisna Jose et al. · 09.03.2023 In synthetic chemistry and pharmacy, the reductive amination reaction is crucial because it is one of the most effective methods for forming C−N bonds. Reductive amination is a reaction that occurs when an amine or ammonia is combined with an aldehy...
ArtikelLate‐Stage Functionalisation of Pyridine‐Containing Bioactive Molecules: Recent Strategies and Perspectivesvon Mattia Failla et al. · 09.03.2023 Mind the gap! A practical guide to navigate through the complex network of selective late-stage functionalisations of pyridine-containing biomolecules. Abstract Late-Stage Functionalisation (LSF) is an innovative technique that has been successful...
ArtikelDesign and Synthesis of Chemiluminescent Cassettes Based on Energy Transfervon Steven Vertueux et al. · 09.03.2023 This article presents a new strategy to obtain near infrared emitting (NIR) chemiluminescent probes. The synthesis of green- or NIR-emitting chemiluminescent cassettes was achieved. Their photophysical study proved that efficient energy transfer occ...
ArtikelRh(III)‐Catalyzed Oxidative Annulation of 2‐Arylquinoxalines with Cyclic 2‐Diazo‐1,3‐diketones by C−H Bond Activationvon Chidrawar Ajay et al. · 09.03.2023 An oxidative C−H bond annulation of 2 arylquinoxalines with cyclic 2-diazo-1,3-diketones has been developed for the synthesis of polycyclic quinoxaline frameworks. This method involves C−H bond activation and double C−C bond formation. Abstract Rh...
ArtikelSynthesis of the N‐Amykitanosyl Tetramic Acid Moiety of Amycolamicinvon Yasuhiro Meguro et al. · 09.03.2023 An N-amykitanosyl tetramic acid derivative, Li's synthetic intermediate for the antibiotic amycolamicin, has been synthesized via stereoconvergent lactamization of a cyclic carbonate-protected N-glycosyl l-valine ester, prepared from l-fucose more e...
ArtikelRegiodivergent Synthesis of 11H‐Indolo[3,2‐c]quinolines and Neocryptolepine from a Common Starting Materialvon Katja S. et al. · 09.03.2023 A common intermediate gives easy access to both neocryptolepine and isocryptolepine analogues in up to 80 % and 95 % yield, respectively. Abstract A large number of diversely functionalized analogs of the bioactive natural products neocryptolepine...
ArtikelAmmonium Acetate Catalyzed Formation of 1,5‐Benzodiazepines through [4+2+1] Cycloaddition Involving 5‐Hydroxymethylfurfuralvon Jingjing Jiang et al. · 07.03.2023 Ammonium acetate in ethanol is a clean and efficient protocol for the multicomponent construction of 1,5-benzodiazepines, being an appropriately mild catalyst in the case of the acid-sensitive biobased platform 5-hydroxymethylfurfural (5-HMF). The p...
ArtikelSunlight‐ or UVA‐Light‐Mediated Synthesis of Hydroxamic Acids from Carboxylic Acidsvon Olga G. et al. · 03.03.2023 A sunlight- or UVA-light-mediated synthesis of hydroxamic acids from carboxylic acids and protected hydroxylamines is reported, the key step of which is the formation of a charge transfer complex. Mechanistic studies by DI-HRMS provide experimental ...
ArtikelDiastereoselective Synthesis of Camptothecin‐like Scaffolds: Construction of a New Class of Pseudo‐natural Productsvon Gourishetty Srikanth et al. · 03.03.2023 Pseudo-natural products (pseudo-NP) strategy has become one of the most important tools to deliver biologically significant chemical probes. In this article, we describe the development of a new class of pseudo-NP collection that led to the synthesi...
ArtikelPhoto‐Driven Direct C−H Arylation of Quinoxalin‐2(1H)‐Ones with Aryltriazenes under Catalyst‐Free and Ambient Conditionsvon Bin Wang et al. · 02.03.2023 A photo-promoted direct arylation of quinoxalin-2(1H)-ones with aryltriazenes under catalyst-free and ambient conditions was developed. The synthetic importance of this methodology was showcased by the simple operation, good functional group toleran...
ArtikelModular Synthesis of Triarylamines and Poly(triarylamine)s through a Radical Mechanismvon Jie Sun et al. · 02.03.2023 The modular synthesis of triarylamines and poly(triarylamine)s has been achieved by using diarylamines and electron-rich arenes as the building blocks. Through the modulation of reaction temperatures, the stepwise assembly of bis-triarylamines could...
ArtikelOne‐Pot Synthesis of Benzodiazepines through RuII‐Catalyzed Regioselective [5+2] Annulation of N‐Aryl Amidines with Alkynyl Cyclobutyl Acetatesvon Jian Shen et al. · 02.03.2023 A highly efficient synthesis of benzo[d][1,3]diazepines has been achieved via RuII-catalyzed regioselective [5+2] annulation reaction of N-Aryl amidines with alkynyl cyclobutyl acetates. Abstract A highly efficient strategy to construct benzo[d][1...
ArtikelAsymmetric Catalytic Approaches Employing α,β‐Unsaturated Iminesvon Suman K. et al. · 01.03.2023 α,β-Unsaturated imines, having diverse reactivity profile, have been exploited as versatile reaction partners in synthetic organic chemistry. This review comprehensively highlights the advancement made in asymmetric catalysis employing various chemi...
ArtikelTotal Synthesis and Biological Evaluation of Seiricuprolide and Pestalotioprolide Bvon Pitipat Sanphetchaloemchok et al. · 01.03.2023 Herein, we report the first and convergent total syntheses of seiricuprolide and pestalotioprolide B, 14-membered macrolides bearing a chiral epoxide moiety. The key synthetic features include OH-directed m-CPBA epoxidation, selective reduction of p...
ArtikelCo(Salox)‐Catalyzed Enantioselective Reduction of α,β‐Unsaturated Estersvon Giacomo Pugliese et al. · 28.02.2023 Easily accessible Salox ligands in combination with cobalt were found to be competent catalysts for the asymmetric conjugate reduction of α,β-unsaturated esters, amides, and nitriles with NaBH4 To give enantioselectivity up to 96.5 : 3.5 er and quan...
ArtikelTowards Green Reductions in Bio‐Derived Solventsvon Serena Perrone et al. · 28.02.2023 The reduction of unsaturated compounds is a powerful tool employed in almost all multistep syntheses. The present Review highlights the recent developments achieved in the field of sustainable reductions of organic compounds in green media: from the...
ArtikelCycloaddition Reactions of Enaminesvon Ilya V. et al. · 23.02.2023 Cycloaddition of enamines leads to the formation of different cyclic compounds with highly valuable structures. This review highlights this topic, discussing advantages, limitations and mechanistic aspects of the related methods over the around two ...
ArtikelSynthetic Approaches to Molecular Fragments of Carbon Allotropesvon Michal Juríček et al. · 23.02.2023 In this Guest Editorial, Michal Juríček and Marcel Mayor introduce the special collection on synthetic approaches to molecular fragments of carbon allotropes.
ArtikelOvercoming Thermodynamically Driven Retro‐Diels‐Alder Reaction through a Cascade One‐Pot Process Exemplified by a Bio‐Based Platform Chemicalvon Bastian Altemeier et al. · 17.02.2023In this contribution, we describe a new approach to apply thermodynamically unfavored reactions in synthetic chemistry and to integrate them in cascade processes. By means of a new developed procedure for multi-step one-pot syntheses, we succeeded in...
ArtikelSyntheses and Preliminary Biological Evaluations of the Dibromopyrrole‐Containing Marine Natural Products Agesasine A, Agesasine B, Longamide E and Various Congenersvon Chengzhi Chen et al. · 13.02.2023Total syntheses of the title marine natural products have been achieved and so confirming the structures originally assigned to them. Upon subjecting agesasine A and its corresponding ethyl ester to Mitsunobu conditions a 1,5-cyclodehydration reactio...
ArtikelSynthesis and Catalytic Studies of Thermoresponsive Copper (I) Complex towards Click Reactionsvon Varnakumar Gayathri et al. · 09.02.2023 To ensure the easy removal of Copper catalyst after click reaction, a thermoresponsive polymer (PNIPAM) is incorporated. As a result, through the volume phase transition behavior of PNIPAM, the catalyst can easily be removed from the system by simpl...
ArtikelStrapped Porphyrins as Model Systems for Atropisomeric Photosensitizer Drugsvon Claire Donohoe et al. · 04.02.2023 Tetrapyrrole shape and distribution of polar substituents have been established as important design considerations for novel photosensitizers. Such parameters were successfully incorporated into the design of novel porphyrins with isomer specific ce...
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