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Unveiling Intramolecular [3+2] Cycloaddition Reactions Leading to Functionalized Heterocycles in the Light of Molecular Electron Density Theory.
Chemphyschem
January 2025
Durgapur Government College, Department of Chemistry, INDIA.
The relative reactivity and cis/trans selectivity of the intramolecular [3+2] cycloaddition (IM32CA) reactions of nitrile oxide (NO), azide (AZ), nitrile sulfide (NS) and nitrile ylide (NY), leading to functionalized heterocycles are studied within the Molecular Electron Density Theory. The kinetically controlled IM32CA reactions are predicted to be cis stereospecific, while the reaction feasibility follows the order NY > NS > NO > AZ with the respective activation Gibbs free energies of 13.7, 17.
View Article and Find Full Text PDFBuilding Three-Dimensional Complexity by Intramolecular 2-Aminoallyl Cation-Diene (4 + 3) Cycloaddition.
Angew Chem Int Ed Engl
January 2025
Nankai University, College of Chemistry, 94 Weijin Rd., 300071, Tianjin, CHINA.
Reliable methods for rapidly constructing C(sp3)-rich three-dimensional polycycles are in high demand for organic synthesis and medicinal chemistry. Although there are various mature systems for synthesizing five- or six-membered polycycles, a catalytic platform for accessing diverse cycloheptanoid-containing polycyclic scaffolds is lacking. Herein, we describe a method for copper-catalyzed intramolecular 2-aminoallyl cation-diene (4 + 3) cycloaddition reactions.
View Article and Find Full Text PDFUnderstanding the Reactivity of "Naked" Acyclic Carbene-like Species Featuring a Group 13 Element in the [4+1] Cycloaddition with Benzene.
Inorg Chem
January 2025
Department of Applied Chemistry, National Chiayi University, Chiayi 60004, Taiwan.
The chemical reactivity between benzene and the "naked" acyclic carbene-like (G13X) species, having two bulky N-heterocyclic boryloxy ligands at the Group 13 center, was theoretically assessed using density functional theory computations. Our theoretical studies show that (BX) preferentially undergoes C-H bond insertion with benzene, both kinetically and thermodynamically, whereas the (AlX) analogue favors a reversible [4 + 1] cycloaddition. Conversely, the heavier carbene analogues ((GaX), (InX), and (TlX)) are not expected to engage in a reaction with benzene.
View Article and Find Full Text PDFCopper-Catalyzed Radical Cascade Cyclization of -Substituted Indole-3-Aldehydes with Aryl Alkenes: Access to Pyrrolo[1,2-]indole Scaffolds.
J Org Chem
January 2025
Pharmacy College, Shandong First Medical University & Shandong Academy of Medical Sciences, Ji'nan 250117, China.
Herein, we report a Cu-DTBP-catalyzed [3 + 2] cycloaddition reaction between 1-(2-oxo-2-phenylethyl)--indole-3-aldehyde and arylalkene, using DMF as the solvent. Under relatively mild reaction conditions, a series of indole compounds were synthesized in moderate yields (up to 73%). This protocol features good functional group tolerance and high atom economy.
View Article and Find Full Text PDFTowards a unified fold-cusp model for bond polarity scaling: electron rearrangements in the pyrolytic isomerization of cubane to cyclooctatetraene.
J Mol Model
January 2025
Departamento de Investigación y Desarrollo, ConsultoresAcademicos SpA, Moneda 1137, 8340457, Santiago, Chile.
Context: This study meticulously examines the criteria for assigning electron rearrangements along the intrinsic reaction coordinate (IRC) leading to bond formation and breaking processes during the pyrolytic isomerization of cubane (CUB) to 1,3,5,7-cyclooctatetraene (COT) from both thermochemical and bonding perspectives. Notably, no cusp-type function was detected in the initial thermal conversion step of CUB to bicyclo[4.2.
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