Consecutive reactions to construct tricarbonyl compounds and synthetic applications thereof

Madroñero, Diego; Mujica-Martinez, C. A.; Vázquez, Alfredo Macías

doi:10.1039/d1ra05187c

Cited by 2 publications

(2 citation statements)

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“…Solvents were described using the SMD continuum solvation model [39] . pKa's were determined using a direct approach at the same level of theory, [40] which has been used before in several systems [41–43] . Natural Bond Orbital analysis, which provided mechanistic details of the activation reaction, was performed by using the NBO Version 3.1 [44] implemented in Gaussian 16.…”

Section: Methodsmentioning

confidence: 99%

“…[39] pKa's were determined using a direct approach at the same level of theory, [40] which has been used before in several systems. [41][42][43] Natural Bond Orbital analysis, which provided mechanistic details of the activation reaction, was performed by using the NBO Version 3.1 [44] implemented in Gaussian 16. Bond properties were determined according to the formalism of reference.…”

Section: Conflict Of Interestsmentioning

confidence: 99%

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Electronic Effect of the [Au(PPh₃)]⁺ Fragment in the Stabilization of Imidazolium Salts and the Destabilization of NHCs

Rosero‐Mafla,

Chaur,

Mujica‐Martinez

et al. 2024

Eur J Inorg Chem

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This work presents the synthesis and characterization of mono (1) and di‐nuclear (2) imidazolium salts stabilized by [AuPPh3]+ fragments. The presence of the gold moiety induces a significant decrease in the carbenic proton's acidic character (high pKa). This high stability is consistent with the pronounced instability of the conjugate bases obtained through deprotonation using strong bases. The formation of carbene species is accompanied by the identification of a 1,2‐rearrangement process in which a preference for the C‐bound species over the N‐bound species is observed. Experimental techniques such as NMR, single‐crystal X‐ray diffraction analysis, mass spectrometry, and computational calculations are employed to investigate the reactivity exhibited by the imidazolium salts. Additionally, the electrochemical properties of the two imidazolium salts were also investigated. This study reveals that both species 1 and 2 display two cathodic peaks which are related to two electro‐chemical irreversible reduction events. The results obtained from both experimental and theoretical studies of this system reveal a strong tendency of the [AuPPh3]+ fragment to stabilize imidazolium salts. Additionally, they demonstrate the preference of this fragment for C‐bound species over N‐bound ones, with the former proving to be highly unstable even under severe conditions of air and moisture exclusion.

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Section: Methodsmentioning

confidence: 99%

Section: Conflict Of Interestsmentioning

confidence: 99%

Electronic Effect of the [Au(PPh₃)]⁺ Fragment in the Stabilization of Imidazolium Salts and the Destabilization of NHCs

Rosero‐Mafla,

Chaur,

Mujica‐Martinez

et al. 2024

Eur J Inorg Chem

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PhI(OAc)₂-mediated aminoacyloxylation of β,γ-unsaturated hydrazones using Togni reagent II as an acyloxyl precursor

Dong-fang

et al. 2023

Org. Biomol. Chem.

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Consecutive reactions to construct tricarbonyl compounds and synthetic applications thereof

Abstract: A cascade process to construct synthetically valuable β-keto-β′-acylcycloalkanecarboxylic acid esters and their transformation into bicyclic and tricyclic systems through intramolecular condensation reactions.

Cited by 2 publications

References 51 publications

Electronic Effect of the [Au(PPh₃)]⁺ Fragment in the Stabilization of Imidazolium Salts and the Destabilization of NHCs

Electronic Effect of the [Au(PPh₃)]⁺ Fragment in the Stabilization of Imidazolium Salts and the Destabilization of NHCs

PhI(OAc)₂-mediated aminoacyloxylation of β,γ-unsaturated hydrazones using Togni reagent II as an acyloxyl precursor

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Consecutive reactions to construct tricarbonyl compounds and synthetic applications thereof

Abstract: A cascade process to construct synthetically valuable β-keto-β′-acylcycloalkanecarboxylic acid esters and their transformation into bicyclic and tricyclic systems through intramolecular condensation reactions.

Cited by 2 publications

References 51 publications

Electronic Effect of the [Au(PPh3)]+ Fragment in the Stabilization of Imidazolium Salts and the Destabilization of NHCs

Electronic Effect of the [Au(PPh3)]+ Fragment in the Stabilization of Imidazolium Salts and the Destabilization of NHCs

PhI(OAc)2-mediated aminoacyloxylation of β,γ-unsaturated hydrazones using Togni reagent II as an acyloxyl precursor

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Electronic Effect of the [Au(PPh₃)]⁺ Fragment in the Stabilization of Imidazolium Salts and the Destabilization of NHCs

Electronic Effect of the [Au(PPh₃)]⁺ Fragment in the Stabilization of Imidazolium Salts and the Destabilization of NHCs

PhI(OAc)₂-mediated aminoacyloxylation of β,γ-unsaturated hydrazones using Togni reagent II as an acyloxyl precursor