• Issue
    Volume 26, Issue 4
    January 24, 2023

Cover Pictures

Free Access

Front Cover: Recent Advances in the Development and Synthesis of Carbohydrate-Based Molecules with Promising Antibacterial Activity (Eur. J. Org. Chem. 4/2023)

  • First Published: 18 January 2023
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The Front Cover represents the lysis of a bacterial cell promoted by a sugar-based, membrane-binding bactericide – an illustrative example of one of the three main classes of sugar-derived antibacterials. Some of the most promising compounds published between 2016 and 2022 are covered in this review, where their design, synthesis, and biological evaluation are concisely explored. Based on the promising bioactivities and innovative mechanisms of action of these compounds, carbohydrates are highlighted as starting points for the development of new solutions for the emerging problem of antimicrobial resistance. More information can be found in the Review by A. M. de Matos.

Reviews

Very Important Paper

Open Access

Recent Advances in the Development and Synthesis of Carbohydrate-Based Molecules with Promising Antibacterial Activity

  • First Published: 17 September 2022
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In this review, the potential of carbohydrates as starting materials for the synthesis of antimicrobial agents is explored. The most recent and successful reports of sugar-based bactericides, bacteriostatic agents, and adhesin binders are covered with focus on the methodologies employed in their synthesis, resulting in a useful compilation of state-of-the-art reactions used in carbohydrate modification.

Organophosphites: An Addition to the Arsenal of Organocatalysts

  • First Published: 15 December 2022
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The development of organophosphite catalysis is introduced in the context of nucleophilic organocatalysis. Its unique characteristics were compared with other known nucleophile catalysts to describe new and complimentary reactions. In this review, we evaluate the reactivity pattern to provide our views on challenges, advantages, and potential applications of phosphite catalyst.

Research Articles

Very Important Paper

Open Access

Combining Matteson Homologations and Claisen Rearrangements – An Efficient Protocol for Amino Acid Synthesis

  • First Published: 15 December 2022
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The Matteson homologation with vinyl nucleophiles can be combined with the zinc-chelated ester enolate Claisen rearrangement to obtain highly functionalized unusual amino acids. The substitution pattern of the side chain can be determined by variation of the nucleophiles used in the homologation steps.

Copper-Catalyzed One-Pot Arylation and Cyclization of Diaryliodonium Salts Derived from o-Iodoanilines for Indolo[2,3-b]indoles Syntheses

  • First Published: 18 December 2022
Description unavailable

A one-pot strategy to access indoloindoles with wide scope and good functional group tolerance from diaryliodonium salts is described.

Gold(I)-Catalyzed and PTSA-Promoted Cycloisomerization of Ynamides to Access Pyrrole Substituted α,β-Unsaturated Ketones

  • First Published: 01 December 2022
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In this work, a new ynamide scaffold has been designed, synthesized and later applied in a gold-catalyzed cycloisomerization reaction to access pyrrole containing α,β-unsaturated ketones in low-to-moderate yields. Interestingly, the trans product has been obtained as a major isomer.

Open Access

Highly Conjugated Bis(benzo[b]phosphole)-P-oxides: Synthesis and Electrochemical, Optical, and Computational Studies

  • First Published: 30 December 2022
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The synthesis of the two diastereoisomers cis-(E)-1 and trans-(E)-1 (the chiral and meso one respectively) containing two stereogenic P atoms has been accomplished in three different ways. This highly conjugated bis-(benzo[b]phosphole) P-oxide has been characterized by means of electrochemical and photophysical studies and the relative configuration of the two diastereoisomers assigned through CV and NMR studies.

Synthesis of 2-Arylpyrimido[4,5-b]porphyrins via Cyclization Reaction with Ammonia

  • First Published: 15 December 2022
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For the first time, a new series of β,β’-fused 2-arylpyrimido[4,5-b]porphyrins were synthesized through an ammonia assimilated condensation cyclization of 2-aroylamino-3-formylporphyrins in DMSO at 50 °C. The preliminary photophysical studies revealed a significant bathochromic shift in electronic absorption and emission spectra of these porphyrinoids as compared to meso-tetrakis(4-chlorophenyl)porphyrins due to the extended π-conjugation.

Synthesis of Cyclic 1,2-Bisphosphines by Tandem Michael Addition of 2,3-Bis(diarylphosphinyl)-1,3-butadiene

  • First Published: 14 December 2022
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In this work, an efficient method for the synthesis of cyclopentyl 1,2-diphosphines from malonates and diphosphinyldienes is reported. The asymmetric version was also accomplished in the presence of a chiral auxiliary. The product can be easily converted into a corresponding transition metal complex, which may be widely used in asymmetric catalysis.

Synthesis and Properties of Bis(naphthofuran)-Fused [7]Helicene Derivatives

  • First Published: 30 December 2022
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Late-stage cyclization of the McMurry dimerized product furnished oxa[7]helicene with functional group tunability.

Visible-Light-Driven One-Pot Synthesis of Benzimidazoles, Benzothiazoles, and Quinazolinones Catalyzed by Scalable and Reusable Ba-Doped CoMoO4 Nanoparticles Under Air Atmosphere

  • First Published: 14 December 2022
Description unavailable

This work reports the visible light mediated oxidative coupling of aryl methyl amines with o-phenylenediamine, 2-aminobenzenethiol and 2-aminobenzamide to benzimidazoles, benzothiazoles, and quinazolinones in one pot using scalable and reusable heterogeneous Ba-doped CoMoO4 nanoparticles under air atmosphere.

Open Access

Nickel-Catalyzed Electrochemical Synthesis of (Hetero)Aryl Trifluoromethyl Selenides

  • First Published: 13 December 2022
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This paper describes an electrochemical nickel-catalyzed reaction of trifluoromethylselenolation of various aryl iodides, catalytic in electron, and using [Me4N]+[SeCF3] as reagent. A Ni(0)-based catalytic cycle was proposed on the basis on electrochemical investigations.

Open Access

Photocatalyzed Synthesis of 3-Substituted Phthalides: A Key Access to (±)-Herbaric Acid

  • First Published: 12 December 2022
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Herein, we investigated a new organophotocatalyzed protocol enabling the preparation of 3-substituted phthalides. From this work, the 1,2,3,5-Tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) turned out to be a particularly efficient organophotocatalyst to promote lactone formation under visible-light irradiation within 6 h. Ultimately, it was found that this protocol could enable the formation of racemic herbaric acid.