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View article: Clove as a Versatile Resource: CuO Nanoparticles and Their Catalytic Role in Eugenol-Based Triazole Synthesis
Clove as a Versatile Resource: CuO Nanoparticles and Their Catalytic Role in Eugenol-Based Triazole Synthesis Open
As eco-friendly processes become central to modern organic synthesis, plant-based materials are emerging as attractive alternatives for both nanoparticle fabrication and catalysis. In this study, we explore the use of clove extract, a natu…
View article: Structural Modifications at the C3 and C30 Positions of the Lupane Skeleton with Carbon-Centered Nucleophiles
Structural Modifications at the C3 and C30 Positions of the Lupane Skeleton with Carbon-Centered Nucleophiles Open
Lupeol, a naturally occurring pentacyclic triterpenoid widely distributed in various medicinal plants, has attracted significant attention due to its diverse pharmacological properties. In this study, we report the synthesis and structural…
View article: Sequential Ester Homologation–Nucleophile‐Guided Functionalization: A Chemoselective Access to Thioesters, Amides, and Acids
Sequential Ester Homologation–Nucleophile‐Guided Functionalization: A Chemoselective Access to Thioesters, Amides, and Acids Open
The homologation of esters—in the presence of a lithium carbenoid—to thioesters, amides, and carboxylic acid is reported. By controlling the tetrahedral intermediate collapsing and promoting a series of rearrangements ultimately leading to…
View article: Chemoselective Synthesis of α‐Chloro and α,α‐Dichloro Acetamidines via the Carbenoids Addition to Inherently Low Electrophilic Carbodiimides
Chemoselective Synthesis of α‐Chloro and α,α‐Dichloro Acetamidines via the Carbenoids Addition to Inherently Low Electrophilic Carbodiimides Open
The hitherto few explored α‐halomethyl amidine motif has been assembled through the addition of a lithiated (di)‐halomethane (i.e., carbenoid) to easily accessible N,N’‐diaryl‐substituted carbodiimides. Despite the inherent low electrophil…
View article: Chemoselective Synthesis of α‐Chloro and α,α ‐Dichloro acetamidines via the Carbenoids Addition to Inherently Low Electrophilic Carbodiimides
Chemoselective Synthesis of α‐Chloro and α,α ‐Dichloro acetamidines via the Carbenoids Addition to Inherently Low Electrophilic Carbodiimides Open
The hitherto few explored α‐halomethyl amidine motif has been assembled through the addition of a lithiated (di)‐halomethane (i.e. carbenoid) to easily accessible N,N’‐diaryl substituted carbodiimides. Despite the inherent low electrophili…
View article: The Versatility of the Roskamp Homologation in Synthesis
The Versatility of the Roskamp Homologation in Synthesis Open
Modern organic synthesis continues to benefit from the flexibility of α-diazo carbonyl intermediates. In the context of homologation processes, the Roskamp reaction—first introduced in 1989—has become a valuable tool due to its selectivity…
View article: Geminal homologative fluorination of carbonyl derivatives <i>en route</i> to 1-fluoro-2-haloethyl skeletons
Geminal homologative fluorination of carbonyl derivatives <i>en route</i> to 1-fluoro-2-haloethyl skeletons Open
Carbonyl groups undergo the sequential installation of two nucleophilic elements, halomethyl and fluoride moieties.
View article: Chemoselective homologative preparation of trisubstituted alkenyl halides from carbonyls and carbenoids
Chemoselective homologative preparation of trisubstituted alkenyl halides from carbonyls and carbenoids Open
The chemoselective synthesis of trisubstituted alkenyl halides (Cl, Br, F, I) starting from ketones and aldehydes and lithium halocarbenoids is reported.
View article: Chemoselective Synthesis of Cyanoformamides from Isocyanates and a Highly Reactive Nitrile Anion <i>Reservoir</i>
Chemoselective Synthesis of Cyanoformamides from Isocyanates and a Highly Reactive Nitrile Anion <i>Reservoir</i> Open
The direct addition of a nitrile anion to isocyanates is reported for a straightforward preparation of valuable cyanoformamides. Through the proper activation of an adequate silicon‐ ate complex precursor (PhMe 2 SiCN) with a Lewis base (p…
View article: Electronic Effects in a Green Protocol for (Hetero)Aryl-S Coupling
Electronic Effects in a Green Protocol for (Hetero)Aryl-S Coupling Open
Aryl and heteroaryl iodides have been efficiently converted into the corresponding thioacetates in cyclopentyl methyl ether (CPME), a green solvent, under Cu catalysis. The chemoselectivity of the reaction is mainly controlled by electroni…
View article: Ruppert‐Prakash Reagent (TMSCF<sub>3</sub>)‐Catalyzed Chemoselective Esterification of Weinreb Amides
Ruppert‐Prakash Reagent (TMSCF<sub>3</sub>)‐Catalyzed Chemoselective Esterification of Weinreb Amides Open
A straightforward TMSCF 3 ‐catalyzed conversion of Weinreb amides into esters through the treatment with sodium alkoxides is reported. The procedure documents a genuine selectivity for the esterification of primary alcohols with Weinreb am…
View article: Homologation reactions for olefin synthesis
Homologation reactions for olefin synthesis Open
View article: CCDC 2191936: Experimental Crystal Structure Determination
CCDC 2191936: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2191935: Experimental Crystal Structure Determination
CCDC 2191935: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: Selective noncovalent proteasome inhibiting activity of trifluoromethyl‐containing<i>gem</i>‐quaternary aziridines
Selective noncovalent proteasome inhibiting activity of trifluoromethyl‐containing<i>gem</i>‐quaternary aziridines Open
The ubiquitin‐proteasome pathway (UPP) represents the principal proteolytic apparatus in the cytosol and nucleus of all eukaryotic cells. Nowadays, proteasome inhibitors (PIs) are well‐known as anticancer agents. However, although three of…
View article: Leveraging the 3-Chloro-4-fluorophenyl Motif to Identify Inhibitors of Tyrosinase from Agaricus bisporus
Leveraging the 3-Chloro-4-fluorophenyl Motif to Identify Inhibitors of Tyrosinase from Agaricus bisporus Open
Tyrosinase (EC 1.14.18.1) is implicated in melanin production in various organisms. There is a growing body of evidence suggesting that the overproduction of melanin might be related to several skin pigmentation disorders as well as neurod…
View article: Base-mediated homologative rearrangement of nitrogen–oxygen bonds of <i>N</i>-methyl-<i>N</i>-oxyamides
Base-mediated homologative rearrangement of nitrogen–oxygen bonds of <i>N</i>-methyl-<i>N</i>-oxyamides Open
Due to the well known reactivity of C(O)–N functionalities towards canonical C1-homologating agents ( e.g. carbenoids, diazomethane, ylides), resulting in the extrusion of the N -centered fragment en route to carbonyl compounds, formal C1-…
View article: Highly chemoselective homologative assembly of the α-substituted methylsulfinamide motif from <i>N</i>-sulfinylamines
Highly chemoselective homologative assembly of the α-substituted methylsulfinamide motif from <i>N</i>-sulfinylamines Open
α-Substituted methylsulfinamide are prepared through the homologation of electrophilic N -sulfinylamines with Li-CHXY reagents.
View article: Novel Class of Proteasome Inhibitors: In Silico and In Vitro Evaluation of Diverse Chloro(trifluoromethyl)aziridines
Novel Class of Proteasome Inhibitors: In Silico and In Vitro Evaluation of Diverse Chloro(trifluoromethyl)aziridines Open
The ubiquitin-proteasome pathway (UPP) is the major proteolytic system in the cytosol and nucleus of all eukaryotic cells. The role of proteasome inhibitors (PIs) as critical agents for regulating cancer cell death has been established. Az…
View article: Application of Biobased Solvents in Asymmetric Catalysis
Application of Biobased Solvents in Asymmetric Catalysis Open
The necessity of more sustainable conditions that follow the twelve principles of Green Chemistry have pushed researchers to the development of novel reagents, catalysts and solvents for greener asymmetric methodologies. Solvents are in ge…
View article: Novel alpha6 preferring GABA-A receptor ligands based on loreclezole
Novel alpha6 preferring GABA-A receptor ligands based on loreclezole Open
View article: Fluoroiodomethane: A CH<sub>2</sub>F‐Moiety‐Delivering Agent Suitable for Nucleophilic‐, Electrophilic‐, and Radical‐Harnessed Operations
Fluoroiodomethane: A CH<sub>2</sub>F‐Moiety‐Delivering Agent Suitable for Nucleophilic‐, Electrophilic‐, and Radical‐Harnessed Operations Open
The recent renewed interest in mono‐fluoromethylation chemistry – somehow less developed than the analogous well‐established trifluoro‐ and difluoro‐methylation tactics – identified the simple C1 building block fluoroiodomethane as an effe…
View article: CCDC 2150363: Experimental Crystal Structure Determination
CCDC 2150363: Experimental Crystal Structure Determination Open
View article: CCDC 2150362: Experimental Crystal Structure Determination
CCDC 2150362: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: Straightforward synthesis of bench-stable heteroatom-centered difluoromethylated entities <i>via</i> controlled nucleophilic transfer from activated TMSCHF<sub>2</sub>
Straightforward synthesis of bench-stable heteroatom-centered difluoromethylated entities <i>via</i> controlled nucleophilic transfer from activated TMSCHF<sub>2</sub> Open
The commercially available difluoromethyltrimethylsilane acts as a valuable difluoromethylating agent for heteroatom-based electrophiles. Upon activation with an alkoxide, a nucleophilic displacement furnishes the corresponding bench-stabl…
View article: CCDC 2081745: Experimental Crystal Structure Determination
CCDC 2081745: Experimental Crystal Structure Determination Open
View article: Consecutive and Selective Double Methylene Insertion of Lithium Carbenoids to Isothiocyanates: A Direct Assembly of Four‐Membered Sulfur‐Containing Cycles
Consecutive and Selective Double Methylene Insertion of Lithium Carbenoids to Isothiocyanates: A Direct Assembly of Four‐Membered Sulfur‐Containing Cycles Open
A formal CH 2 −CH 2 homologation conducted with C1 carbenoids on a carbon electrophile for the obtainment of a four‐membered cycle is reported. The logic proposes the consecutive delivery of two single nucleophilic CH 2 units to an isothio…
View article: Consecutive and Selective Double Methylene Insertion of Lithium Carbenoids to Isothiocyanates: A Direct Assembly of Four‐Membered Sulfur‐Containing Cycles
Consecutive and Selective Double Methylene Insertion of Lithium Carbenoids to Isothiocyanates: A Direct Assembly of Four‐Membered Sulfur‐Containing Cycles Open
A formal CH 2 −CH 2 homologation conducted with C1 carbenoids on a carbon electrophile for the obtainment of a four‐membered cycle is reported. The logic proposes the consecutive delivery of two single nucleophilic CH 2 units to an isothio…
View article: Pseudo-Dipeptide Bearing α,α-Difluoromethyl Ketone Moiety as Electrophilic Warhead with Activity against Coronaviruses
Pseudo-Dipeptide Bearing α,α-Difluoromethyl Ketone Moiety as Electrophilic Warhead with Activity against Coronaviruses Open
The synthesis of α-fluorinated methyl ketones has always been challenging. New methods based on the homologation chemistry via nucleophilic halocarbenoid transfer, carried out recently in our labs, allowed us to design and synthesize a tar…
View article: CCDC 2016506: Experimental Crystal Structure Determination
CCDC 2016506: Experimental Crystal Structure Determination Open