A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety

Taydakov, Ilya V.; Kreshchenova, Yuliya M; Dolotova, Ekaterina P

doi:10.3762/bjoc.14.290

Cited by 13 publications

(4 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For verification and interpretation of data obtained, the DFT simulations were performed. In our previous study, we demonstrate the predomination of the enol form for both ligands. The calculations at the cc-pVDZ/DFT/PBE0/SMD level showed greater thermodynamic stability for one of the possible tautomers of the enol form (Figure ).…”

Section: Resultsmentioning

confidence: 64%

See 1 more Smart Citation

Behavior of Some Perfluorinated Analogs of Thenoyltrifluoroacetone in Aqueous Solution

2019

View full text Add to dashboard Cite

The acid–base properties, protonation activity, and complexing abilities of two substituted β-diketones have been studied. The equilibrium constants of dissociation (pK a) were obtained at constant ionic strength (I = 0.5 M) in the pH 2.0–7.5 region. Protonation processes have been investigated in a strongly acidic solution of HCl for the determination of protonation constants (−pK H). All received acid–base parameters characterize both ligands as more acidic compounds than thenoyltrifluoroacetone. The study of complexation with 11 lanthanides (Ce, Nd, Pr, Sm, Eu, Gd, Dy, Er, Tm, Yb, and Lu) was carried out in glycine buffer. The determined values of formation constants for monocomplex species lie in the region from 5.5 to 6.9 logarithmic units. Using DFT procedures, the optimal computational protocol for describing the studied equilibria has been found.

show abstract

Section: Resultsmentioning

confidence: 64%

“…1,3-Diketones were synthesized through the Claisen-type condensation of 2-acetylthiophene with corresponding esters of perfluorinated carboxylic acids according to previously published procedures. − The additional purification of products was performed by vacuum distillation. The purity of the ligands (≥96%) has been estimated using NMR.…”

Section: Methodsmentioning

confidence: 99%

Behavior of Some Perfluorinated Analogs of Thenoyltrifluoroacetone in Aqueous Solution

2019

View full text Add to dashboard Cite

show abstract

“…The Claisen condensation is known as the main synthetic method for the preparation of fluorinated β-diketones. The most frequently used condensing agents are NaH [31][32][33][34][35] and MeONa [36][37][38][39][40][41][42][43], while LiH [44][45][46][47][48], LDA [49] and Na [50] are less demanded. Ethers (DME, Et2O, THF) are more pre ferred solvents rather than benzene or alcohols.…”

Section: The Synthesis Of Fluorinated Ligands Containing the β-Dicarb...mentioning

confidence: 99%

Heterometallic Molecular Architectures Based on Fluorinated β-Diketone Ligands

et al. 2022

View full text Add to dashboard Cite

This review summarizes the data on the synthesis of coordination compounds containing two or more different metal ions based on fluorinated β-diketonates. Heterometallic systems are of high interest in terms of their potential use in catalysis, medicine and diagnostics, as well as in the development of effective sensor devices and functional materials. Having a rich history in coordination chemistry, fluorinated β-diketones are well-known ligands generating a wide variety of heterometallic complexes. In this context, we focused on both the synthetic approaches to β-dicarbonyl ligands with additional coordination centers and their possible transformations in complexation reactions. The review describes bi- and polynuclear structures in which β-diketones are the key building blocks in the formation of a heterometallic framework, including the examples of both homo- and heteroleptic complexes.

show abstract

“…These compounds were further employed for the synthesis of trifluoromethyl pyrazoles, compounds that present biological activity, as commented before. In 2018, a method for the preparation of a set of 2-thienyl diketones 64 with different lengths of a perfluorinated side has been described, as shown in Scheme 9b [80]. Initial studies were carried out by the Claisen condensation between 2-acetylthiophene 62 and fluorinated esters 63 in the presence of different bases employing anhydrous Et 2 O as a solvent in the presence of highly active alkoxides as NaOMe or NaOEt.…”

Section: Preparation Of Halogenated Diketonesmentioning

confidence: 99%

Recent Developments in the Synthesis of β-Diketones

Gonzalo

Alcántara

2021

Pharmaceuticals

View full text Add to dashboard Cite

Apart from being one of the most important intermediates in chemical synthesis, broadly used in the formation of C–C bonds among other processes, the β-dicarbonyl structure is present in a huge number of biologically and pharmaceutically active compounds. In fact, mainly derived from the well-known antioxidant capability associated with the corresponding enol tautomer, β-diketones are valuable compounds in the treatment of many pathological disorders, such as cardiovascular and liver diseases, hypertension, obesity, diabetes, neurological disorders, inflammation, skin diseases, fibrosis, or arthritis; therefore, the synthesis of these structures is an area of overwhelming interest for organic chemists. This paper is devoted to the advances achieved in the last ten years for the preparation of 1,3-diketones, using different chemical (Claisen, hydration of alkynones, decarboxylative coupling) or catalytic (biocatalysis, organocatalytic, metal-based catalysis) methodologies: Additionally, the preparation of branched β-dicarbonyl compounds by means of α-functionalization of non-substituted 1,3-diketones are also discussed.

show abstract

A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety

Cited by 13 publications

References 31 publications

Behavior of Some Perfluorinated Analogs of Thenoyltrifluoroacetone in Aqueous Solution

Behavior of Some Perfluorinated Analogs of Thenoyltrifluoroacetone in Aqueous Solution

Heterometallic Molecular Architectures Based on Fluorinated β-Diketone Ligands

Recent Developments in the Synthesis of β-Diketones

Contact Info

Product

Resources

About