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Featured Reviews in Organic Chemistry 2025
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Featured Reviews in Organic Chemistry 2025

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: 31 July 2025 | Viewed by 2231

Special Issue Editor

Prof. Dr. Roman Dembinski

E-Mail Website
Guest Editor
Department of Chemistry, Oakland University, 146 Library Drive, Rochester, MI 48309-4479, USA
Interests: organic, organometallic, and medicinal chemistry; organic synthesis; nucleosides; heterocycles; alkynes; fluorine and fluorous; cycloisomerizations; cyclizations
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

We have just completed the Special Issue “Featured Reviews in Organic Chemistry 2024”, which was a compilation of articles reaching across a variety of the areas in modern organic chemistry.

Based on readers’ continuous interest, we are pleased to announce the next edition of this Special Issue, which will be titled “Featured Reviews in Organic Chemistry 2025”. This Special Issue of Molecules (MDPI) is seeking contributions that review any area of research in organic chemistry that has broad appeal and is positioned within the scope of the journal. Summaries of the most recent, innovative developments in organic chemistry, synthesis, etc., are welcome. The contributions should critically summarize a range of organic studies, methodologies, or reactions; examine previously unaddressed aspects; propose and develop new approaches; exchange perspectives; or encourage new lines of study. Beyond the classical areas, other specific subfields, including, but not limited to, catalysis, flow, mechanochemistry, medicinal chemistry, bioorganic chemistry, or interdisciplinary studies, are welcome. The major goal of this Special Issue is to collect concise articles from prominent authors representing modern directions in the broad field of organic chemistry. We hope that your well-regarded research group will participate in this prestigious, visible, and publisher-promoted Special Issue of featured reviews.

Prof. Dr. Roman Dembinski
Guest Editor

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

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Published Papers (2 papers)

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Review

36 pages, 10506 KiB  
Review
HOF•CH3CN—The Most Potent Oxygen Transfer Agent for a Large Variety of Organic Molecules
by Shlomo Rozen
Molecules 2025, 30(6), 1248; https://doi.org/10.3390/molecules30061248 - 11 Mar 2025
Viewed by 679
Abstract
The complex of hypofluorous acid with acetonitrile—HOF•CH3CN—is the only substance possessing a truly electrophilic oxygen. This fact makes it the only tool suitable for transferring oxygen atoms to sites that are not accessible to this vital element. We will review here [...] Read more.
The complex of hypofluorous acid with acetonitrile—HOF•CH3CN—is the only substance possessing a truly electrophilic oxygen. This fact makes it the only tool suitable for transferring oxygen atoms to sites that are not accessible to this vital element. We will review here most of the known organic reactions with this complex, which is easily made by bubbling dilute fluorine through aqueous acetonitrile. The reactions of HOF•CH3CN with double bonds produce epoxides in a matter of minutes at room temperature, even when the olefin is electron-depleted and cannot be epoxidized by any other means. The electrophilic oxygen can also substitute deactivated tertiary C-H bonds via electrophilic substitution, proceeding with full retention of configuration. Using this complex enables transferring oxygen atoms to a carbonyl and oxidizing alcohols and ethers to ketones. The latter could be oxidized to esters via the Baeyer–Villiger reaction, proving once again the validity of the original Baeyer mechanism. Azines are usually avoided as protecting groups for carbonyl since their removal is problematic. HOF•CH3CN solves this problem, as it is very effective in recreating carbonyls from the respective azines. A bonus of the last reaction is the ability to replace the common 16O isotope of the carbonyl with the heavier 17O or 18O in the simplest and cheapest possible way. The reagent can transfer oxygen to most nitrogen-containing molecules. Thus, it turns practically any azide or amine into nitro compounds, including amino acids. This helps to produce novel α-alkylamino acids. It also attaches oxygen atoms to most tertiary nitrogen atoms, including certain aromatic ones, which could not be obtained before. HOF•CH3CN was also used to make five-member cyclic poly-NO derivatives, many of them intended to be highly energetic materials. The nucleophilic sulfur atom also reacts very smoothly with the reagent in a wide range of compounds to form sulfone derivatives. While common sulfides are easily converted to sulfones by many orthodox reagents, electron-depleted ones, such as Rf-S-Ar, can be oxidized to Rf-SO2-Ar only with this reagent. The mild reaction conditions also make it possible to synthesize a whole range of novel episulfones and offer, as a bonus, a very easy way to make SxO2, x being any isotope variation of oxygen. These mild conditions also helped to oxidize thiophene to thiophen-S,S-dioxide without the Diels–Alder dimerizations, which usually follow such dioxide formation. The latter reaction was a prelude to a series of preparations of [all]-S,S-dioxo-oligothiophenes, which are important for the efficient preparation of active layers in field-effect transistors (FETs), as such oligomers are considered to be important for organic semiconductors for light-emitting diodes (LEDs). Several types of these oligothiophenes were prepared, including partly or fully oxygenated ones, star-oligothiophenes, and fused ones. Several [all]-S,S-dioxo-oligo-thienylenevinylenes were also successfully prepared despite the fact that they also possess carbon–carbon p centers in their molecules. All oxygenated derivatives have been prepared for the first time and have lower HOMO-LUMO gaps compared to their parent compounds. HOF•CH3CN was also used to oxidize the surface of the nanoparticles of oligothiophenes, leaving the core of the nanoparticle unchanged. Several highly interesting features have been detected, including their ability to photostimulate the retinal neurons, especially the inner retinal ones. HOF•CH3CN was also used on elements other than carbon, such as selenium and phosphor. Various selenides were oxidized to the respective selenodioxide derivatives (not a trivial task), while various phosphines were converted efficiently to the corresponding phosphine oxides. Full article
(This article belongs to the Special Issue Featured Reviews in Organic Chemistry 2025)
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Graphical abstract

45 pages, 12731 KiB  
Review
Recent Developments in Stereoselective Reactions of Sulfoxonium Ylides
by Ciarán O’Shaughnessy, Mukulesh Mondal and Nessan J. Kerrigan
Molecules 2025, 30(3), 655; https://doi.org/10.3390/molecules30030655 - 1 Feb 2025
Viewed by 1322
Abstract
This review probes the recent developments in stereoselective reactions within the area of sulfoxonium ylide chemistry since the early 2000s. An abundance of research has been applied to sulfoxonium ylide chemistry since its emergence in the early 1960s. There has been a continued [...] Read more.
This review probes the recent developments in stereoselective reactions within the area of sulfoxonium ylide chemistry since the early 2000s. An abundance of research has been applied to sulfoxonium ylide chemistry since its emergence in the early 1960s. There has been a continued effort since then with work in traditional areas, such as epoxidation, aziridination and cyclopropanation. Efforts have also been applied in novel areas, such as olefination and insertion reactions, to develop stereoselective methodologies using organocatalysis and transition metal catalysis. The growing research area of interrupted Johnson–Corey–Chaykovsky reactions is also described, whereby unexpected stereoselective cyclopropanation and epoxidation methodologies have been developed. In general, the most observed mechanistic pathway of sulfoxonium ylides is the formal cycloaddition: (2 + 1) (e.g., epoxides, cyclopropanes, aziridines), (3 + 1) (e.g., oxetanes, azetidines), (4 + 1) (e.g., indanones, indolines). This pathway involves the formation of a zwitterionic intermediate through nucleophilic addition of the carbanion to an electrophilic site. An intramolecular cyclization occurs, constructing the cyclic product. Insertion reactions of sulfoxonium ylides to X–H bonds (e.g., X = S, N or P) are also observed, whereby protonation of the carbanion is followed by a nucleophilic addition of X, to form the inserted product. Full article
(This article belongs to the Special Issue Featured Reviews in Organic Chemistry 2025)
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