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Relevant academic research and scientific papers

Mild and efficient palladium-catalyzed direct trifluoroethylation of aromatic systems by C-H activation

The introduction of trifluoroalkyl groups into aromatic molecules is an important transformation in the field of organic and medicinal chemistry. However, the direct installation of fluoroalkyl groups onto aromatic molecules still represents a challenging and highly demanding synthetic task. Herein, a simple trifluoroethylation process that relies on the palladium-catalyzed C-H activation of aromatic compounds is described. With the utilization of a highly active trifluoroethyl(mesityl)iodonium salt, the developed catalytic method enables the first highly efficient and selective trifluoroethylation of aromatic compounds. The robust catalytic procedure provides the desired products in up to 95 % yield at 25 °C in 1.5 to 3 hours and tolerates a broad range of functional groups. The utilization of hypervalent reagents opens new synthetic possibilities for direct alkylations and fluoroalkylations in the field of transition-metal-catalyzed C-H activation.

Synthesis, characterization and density functional theory investigations of monoacyl aniline derivatives

We synthesized a number of aniline derivatives containing acyl groups to compare their barriers of rotation around the N-CO groups. Geometry optimization for all the rotamers have been performed using density functional theory (DFT) at the B3LYP/6-31G** level of theory. For each stationary point we carried out vibrational frequency calculations at the same level to characterize their nature as minima or transition states. The methoxy group substituent on the benzene ring causes some changes in the C-C bond distances. We carried out potential energy surface scanning to find out all possible low-energy conformations, which would be used as the initial structure for further molecular calculations. There were only three kinds of conformations with local minimum potential energy and two transition states. The optimized bond lengths and bond angles are in better agreement with the experimental values.

Transformation of thioamide compounds to corresponding amides using 12-Tungstosilicic acid

12-Tungstosilicic acid (H4SiW12O40) is applied for the conversion of a series of thioamides to their corresponding oxo analogues in excellent yields in acetonitrile. In the case of thioketones, no reaction is observed under these conditions. The reusability of the catalyst also is investigated.

Acidified, wet, silica-supported tetrabutylammonium periodate: A convenient and mild reagent for conversion of thioamides to their corresponding amides under solvent-free conditions

A series of thioamides are transformed to their corresponding oxo analogues in good to excellent yields with acidified, wet, silica-supported tetrabutylammonium periodate under solvent-free conditions.

A mild and convenient method for conversion of thioamides to their corresponding amides using acidified wet silica-supported permanganate under solvent-free conditions

A mild and efficient method for conversion of thioamides to their corresponding amides is reported. A series of thioamides are transformed to their corresponding carbonyl compounds in good to excellent yields by acidified wet silica-supported permanganate under solid phase conditions.

Efficient and convenient deprotection of thiocarbonyl to carbonyl compounds using 3-carboxypyridinium and 2,2′-bipyridinium chlorochromates in solution, dry media, and under microwave irradiation

A synthetic utility of 3-carboxypyridinium (CPCC) and 2,2′- bipyridinium (BPCC) chlorochromates in deprotection reactions is reported. Different types of thioamides, thioureas, thiono esters, and thioketones are deprotected to their corresponding carbonyl compounds with these reagents in good to excellent yields. The reactions were carried out in solution, under solvent-free conditions, and under microwave irradiation. The results show that with both reagents the rates of the reactions and the yields are usually highest under microwave irradiation. Springer-Verlag 2003.

Intramolecular charge transfer with N-benzoylaminonaphthalenes. 1-Aminonaphthalene versus 2-aminonaphthalene as electron donors

N-(substituted-benzoyl)-1-aminonaphthalenes and N-(substituted-benzoyl)-2-aminonaphthalenes (1-NBAs and 2-NBAs) with varied substituents at the para- or meta-position of benzoylphenyl ring were prepared to probe the difference between 1-aminonaphthalene (1-AN) and 2-aminonaphthalene (2-AN) as electron donors, using benzanilide-like charge transfer as a probe reaction. An abnormal long-wavelength emission was found for all of the prepared aminonaphthalene derivatives in cyclohexane and was assigned to the CT state by the observation of a substantial red shift with increasing solvent polarity or with increasing electron-withdrawing ability of the substituent. The CT emission energies were found to follow a linear relationship with the Hammett constant of the substituent and the value of the linear slope for 1-NBAs (-0.45 eV) was higher than that of 2-NBAs(-0.35 eV), the latter being close to that of the aniline derivatives (BAs, -0.345 eV). This pointed to a higher extent of charge separation in the CT state of 1-NBAs in which a full charge separation was established by the reduction potential dependence of the CT emission energy with a linear slope of -1.00. The possible contribution of the difference in the steric effect and the electron donating ability of the donors in 1-NBAs and 2-NBAs was ruled out by the observation that the corresponding linear slopes of benzoyl-substituted BAs remained unchanged when para-, meta-, ortho-, or ortho, ortho-methyls were introduced into the aniline moiety. It was therefore concluded that 1-AN enhanced the charge transfer in 1-NBAs and the proximity of its 1La and 1Lb states was suggested to be responsible. Results showed that the charge transfers in 1-NBAs and 2-NBAs were not the same and 1-AN and 2-AN as electron donors were different not only in electron donating ability but in shaping the charge transfer pathways as well.

Bismuth(III) nitrate pentahydrate: A convenient and selective reagent for conversion of thiocarbonyls to their carbonyl compounds

A variety of thioamides and thioureas are rapidly transformed to their oxo derivatives with Bi(NO3)3·5H2O in excellent yields. However, thiono esters and thioketones are converted to their corresponding carbonyl compounds in only poor yields. Bi(NO3)3·5H2O is relatively non-toxic, insensitive to air and inexpensive. These features coupled with the selective deprotection of thioamides and thioureas in the presence of thiono esters and thioketones make this method an attractive alternative to the existing routes for deprotection of thiocarbonyl compounds.

A facile and convenient method for deprotection of thiocarbonyls to their carbonyl compounds using oxone under aprotic and nonaqueous conditions

The reaction of oxone as an inexpensive, stable, and commercially available reagent with thiocarbonyl compounds in refluxing acetonitrile has been studied. Primary, secondary, and tertiary thioamides and thioureas are converted to their oxo analogues efficiently. Thiono esters also are transformed to their corresponding esters, while thioketones remained intact under these conditions.

A convenient and inexpensive method for conversion of thiocarbonyl compounds to their oxo derivatives using oxone under solvent-free conditions

A series of thioamides, thioureas and thioesters are transformed to their corresponding carbonyl compounds in good to excellent yields with oxone under solid phase conditions, while thioketones remained unchanged under these conditions.