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A Molecular Electron Density Theory Study of the Domino Reaction of IN/I-Phenyl Iminoboranes with Benzaldehyde Yielding Fused Bicyclic Compounds

Molecules (Basel, Switzerland), 2023-08, Vol.28 (17) [Peer Reviewed Journal]

COPYRIGHT 2023 MDPI AG ;ISSN: 1420-3049 ;EISSN: 1420-3049 ;DOI: 10.3390/molecules28176211

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  • Title:
    A Molecular Electron Density Theory Study of the Domino Reaction of IN/I-Phenyl Iminoboranes with Benzaldehyde Yielding Fused Bicyclic Compounds
  • Author: Domingo, Luis R ; Aurell, María José ; Ríos-Gutiérrez, Mar
  • Subjects: Aldehydes ; Analysis ; Chemical properties
  • Is Part Of: Molecules (Basel, Switzerland), 2023-08, Vol.28 (17)
  • Description: The reaction of N-phenyl iminoborane with benzaldehyde yielding a fused aromatic compound, recently reported by Liu et al., has been studied within the Molecular Electron Density Theory (MEDT). Formation of the fused aromatic compound is a domino process that comprises three consecutive reactions: (i) formation of a weak molecular complex between the reagents; (ii) an intramolecular electrophilic attack of the activated carbonyl carbon of benzaldehyde on the ortho position of the N-phenyl substituent of iminoborane; and (iii) a formal 1,3-hydrogen shift yielding the final fused aromatic compound. The two last steps correspond to a Friedel–Crafts acylation reaction, the product of the second reaction being the tetrahedral intermediate of an electrophilic aromatic substitution reaction. However, the presence of the imino group adjacent to the aromatic ring strongly stabilizes the corresponding intermediate, being the reaction product when the ortho positions are occupied by t-butyl substituents. This domino reaction shows a great similitude with the Brønsted acid catalyzed Povarov reaction. Although N-phenyl iminoborane can experience a formal [2+2] cycloaddition reaction with benzaldehyde, its higher activation Gibbs free energy compared to the intramolecular electrophilic attack of the activated carbonyl carbon of benzaldehyde on the ortho position of the N-phenyl substituent, 6.6 kcal·mol[sup.−1], prevents the formation of the formal [2+2] cycloadduct. The present MEDT study provides a different vision of the molecular mechanism of these reactions based on the electron density.
  • Publisher: MDPI AG
  • Language: English
  • Identifier: ISSN: 1420-3049
    EISSN: 1420-3049
    DOI: 10.3390/molecules28176211
  • Source: Open Access: DOAJ Directory of Open Access Journals
    Open Access: PubMed Central
    Geneva Foundation Free Medical Journals at publisher websites
    AUTh Library subscriptions: ProQuest Central
    Alma/SFX Local Collection
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