A DFT study of the mechanism of Brønsted acid catalysed Povarov reactions

Ríos‐Gutiérrez, Mar; Layeb, Hatem; Domingo, Luís R.

doi:10.1016/j.tet.2015.10.012

Cited by 18 publications

(14 citation statements)

References 72 publications

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“…ELF topological analysis for the C–C bond formation along the nucleophilic addition of 2-hydroxyprop-2-yl free radical 7u to electrophilic methyl acrylate evidenced that the new C–C bond is formed through the C-to-C coupling of two radical centers, which were properly characterised through the use of the Parr functions [68]. Besides, radical Parr functions Pko have also shown to be an applicable tool to analyse the most electrophilic and nucleophilic centers in cationic and anionic organic molecules participating in ionic reactions [41,69].…”

Section: Conceptual Dftmentioning

confidence: 99%

Applications of the Conceptual Density Functional Theory Indices to Organic Chemistry Reactivity

2016

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Theoretical reactivity indices based on the conceptual Density Functional Theory (DFT) have become a powerful tool for the semiquantitative study of organic reactivity. A large number of reactivity indices have been proposed in the literature. Herein, global quantities like the electronic chemical potential µ, the electrophilicity ω and the nucleophilicity N indices, and local condensed indices like the electrophilic Pk and nucleophilic Pḱ Parr functions, as the most relevant indices for the study of organic reactivity, are discussed.

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Section: Conceptual Dftmentioning

confidence: 99%

Applications of the Conceptual Density Functional Theory Indices to Organic Chemistry Reactivity

2016

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“…[20] In addition to these experimental evidences, computational results have shown that the stepwise mechanism is preferred (or, at least, competitive) to the concerted one. L. R. Domingo et al, using Density Functional Theory (DFT), studied the effect of both Brønsted [47] and Lewis acid catalysis [48] on the PR, showing lower activation barriers related to the non-concerted process. However, the same group showed that for the oxa-PR, in which the hetero-diene is an oxocarbenium, the lowest-Scheme 4.…”

Section: Mechanistic Aspectsmentioning

confidence: 99%

Enantioselective Povarov Reactions: An Update of a Powerful Catalytic Synthetic Methodology

et al. 2022

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The enantioselective Povarov reaction is one of the most powerful synthetic strategy to synthesize chiral, highly functionalized 1,2,3,4-tetrahydroquinolines. The present Minireview aims to collect the most significant successful examples of highly efficient enantioselective catalytic protocols for this reaction, since 2014. A comprehensive discussion of different catalytic strategies employed in recent years to realize the enantioselec-tive Povarov reaction is provided; the use of chiral phosphoric acids, thio(urea) and proline derivatives, as well as transition metal complexes will be presented. Additionally, this Minireview critically discusses the intriguing and yet obscure mechanistic pathways of this well-known reaction, the controversial dispute between a concerted or a polar two-step process.

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“…Domingo's group has been actively contributing to the study of the mechanism of Povarov reactions via formal [4+2] cycloadducts. [16][17][18][19][20] These authors, using density functional theory (DFT) methods and different levels of theory for different substrates, have contributed to the understanding of the regioselectivity and the stereoselectivity of Povarov reactions.…”

Section: Mechanism Of the Povarov Reactionmentioning

confidence: 99%

The Povarov Reaction: A Versatile Method to Synthesize Tetrahydroquinolines, Quinolines and Julolidines

et al. 2022

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Multicomponent Povarov reaction is a powerful approach for the construction of N-heterocyclic containing substances. By using Povarov reaction, in addition to accessing tetrahydroquinolines, quinolines and julolidines in a single step, it is possible to form, respectively, two new Csp3-Csp3 and one Csp3-Nsp3 bonds, two new Csp2-Csp2 and one Csp2-Nsp2 bonds and four Csp3-Csp3 and two Csp3-Nsp1 bonds. This review article reports the main features of the Povarov reaction such as its mechanism, the scope of such reaction concerning to different catalysts and substrates used on it as well as the stereoselective versions of Povarov reaction

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A DFT study of the mechanism of Brønsted acid catalysed Povarov reactions

Cited by 18 publications

References 72 publications

Applications of the Conceptual Density Functional Theory Indices to Organic Chemistry Reactivity

Applications of the Conceptual Density Functional Theory Indices to Organic Chemistry Reactivity

Enantioselective Povarov Reactions: An Update of a Powerful Catalytic Synthetic Methodology

The Povarov Reaction: A Versatile Method to Synthesize Tetrahydroquinolines, Quinolines and Julolidines

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