28078-83-3

Upstream product

• 771-60-8 2,3,4,5,6-pentafluoroaniline 
• 98-88-4 benzoyl chloride 
• 64317-34-6 N-(pentafluorophenyl)carbonimidoyl dichloride 
• 65-85-0 benzoic acid 
• 1423-15-0 perfluorophenyl azide 
• 100-52-7 benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 104-87-0 4-methyl-benzaldehyde 
• 555-16-8 4-nitrobenzaldehdye 
• 104-88-1 4-chlorobenzaldehyde 
• 100-42-5 styrene 
• 344-04-7 bromopentafluorobenzene 
• 55-21-0 benzamide 
• 93-58-3 benzoic acid methyl ester 

Downstream Products

• 31478-75-8 N-phenyltetrafluorobenzoxazole 
• 70016-02-3 2-Phenyl-4,5,6,7-tetrafluorobenzothiazole 
• 1355020-35-7 ethyl 2-{3-oxo-2-(perfluorophenyl)isoindolin-1-yl}acetate 
• 87228-28-2 N-(pentafluorophenyl)-benzimidoyl chloride 
• 3002-30-0 methyl 9H-fluorene-9-carboxylate 
• 555-21-5 4-Nitrophenylacetonitrile 
• 413613-58-8 C₁₃H₅F₆NO 

Relevant academic research and scientific papers

Ligand-Promoted RhIII-Catalyzed Thiolation of Benzamides with a Broad Disulfide Scope

A ligand-promoted RhIII-catalyzed C(sp2)?H activation/thiolation of benzamides has been developed. Using bidentate mono-N-protected amino acid ligands led to the first example of RhIII-catalyzed aryl thiolation reactions directed by weakly coordinating directing amide groups. The reaction tolerates a broad range of amides and disulfide reagents.

Highly Chemoselective, Transition-Metal-Free Transamidation of Unactivated Amides and Direct Amidation of Alkyl Esters by N-C/O-C Cleavage

The amide bond is one of the most fundamental functional groups in chemistry and biology and plays a central role in numerous processes harnessed to streamline the synthesis of key pharmaceutical and industrial molecules. Although the synthesis of amides is one of the most frequently performed reactions by academic and industrial scientists, the direct transamidation of tertiary amides is challenging due to unfavorable kinetic and thermodynamic contributions of the process. Herein, we report the first general, mild, and highly chemoselective method for transamidation of unactivated tertiary amides by a direct acyl N-C bond cleavage with non-nucleophilic amines. This operationally simple method is performed in the absence of transition metals and operates under unusually mild reaction conditions. In this context, we further describe the direct amidation of abundant alkyl esters to afford amide bonds with exquisite selectivity by acyl C-O bond cleavage. The utility of this process is showcased by a broad scope of the method, including various sensitive functional groups, late-stage modification, and the synthesis of drug molecules (>80 examples). Remarkable selectivity toward different functional groups and within different amide and ester electrophiles that is not feasible using existing methods was observed. Extensive experimental and computational studies were conducted to provide insight into the mechanism and the origins of high selectivity. We further present a series of guidelines to predict the reactivity of amides and esters in the synthesis of valuable amide bonds by this user-friendly process. In light of the importance of the amide bond in organic synthesis and major practical advantages of this method, the study opens up new opportunities in the synthesis of pivotal amide bonds in a broad range of chemical contexts.

Synthesis of nanomagnetic supported thiourea–copper(I) catalyst and its application in the synthesis of triazoles and benzamides

A novel nanomagnetic supported thiourea–copper(I) complex and inorganic–organic Takemoto-like hybrid nanomagnetic catalyst was designed, and synthesized. The prepared naomagnetic catalyst was characterized using Fourier transform infrared spectroscopy, X-ray diffraction, energy-dispersive X-ray analysis, transmission and scanning electron microscopies, thermogravimetry, nitrogen adsorption/desorption, zeta potential and vibrating sample magnetometry. Furthermore, the fabricated dual-role inorganic–organic hybrid catalyst shows a striking and robust catalytic activity for the synthesis of triazoles and benzamides through click and coupling reactions, respectively, under mild and eco-friendly reaction conditions.

Ligand-Promoted Rhodium(III)-Catalyzed ortho-C?H Amination with Free Amines

Ligand development for rhodium(III)-catalyzed C?H activation reactions has largely been limited to cyclopentadienyl (Cp) based scaffolds. 2-Methylquinoline has now been identified as a feasible ligand that can coordinate to the metal center of Cp*RhCl to accelerate the cleavage of the C?H bond of N-pentafluorophenylbenzamides, providing a new structural lead for ligand design. The compatibility of this reaction with secondary free amines and anilines also overcomes the limitations of palladium(II)-catalyzed C?H amination reactions.

Ligand-Promoted Rh(III)-Catalyzed Coupling of Aryl C-H Bonds with Arylboron Reagents

Rhodium(III)-catalyzed C-H arylation of arenes with phenylboronic acid pinacol esters has been achieved using a readily removable N-pentafluorophenylbenzamide directing group for the first time. The use of a bidentate phosphine ligand (Binap) significantly increased the yield of the cross-coupling of C-H bonds with organoboron reagents.

Selective radical amination of aldehydic C(sp2)-H bonds with fluoroaryl azides via Co(ii)-based metalloradical catalysis: Synthesis of N-fluoroaryl amides from aldehydes under neutral and nonoxidative conditions

The Co(ii) complex of the D2h-symmetric amidoporphyrin 3,5-DitBu-IbuPhyrin, [Co(P1)], has proven to be an effective metalloradical catalyst for intermolecular amination of C(sp2)-H bonds of aldehydes with fluoroaryl azides. The [Co(P1)]-catalyzed process can employ aldehydes as the limiting reagents and operate under neutral and nonoxidative conditions, generating nitrogen gas as the only byproduct. The metalloradical aldehydic C-H amination is suitable for different combinations of aldehydes and fluoroaryl azides, producing the corresponding N-fluoroaryl amides in good to excellent yields. A series of mechanistic studies support a stepwise radical mechanism for the Co(ii)-catalyzed intermolecular C-H amination. This journal is the Partner Organisations 2014.

Copper-mediated direct aryloxylation of benzamides assisted by an N, O -bidentate directing group

Copper-mediated selective mono- or diaryloxylation of benzamides has been achieved by using 2-aminopyridine 1-oxide as a new and removable N,O-bidentate directing group. The reaction system shows a broad substrate scope and provides a straightforward way for the synthesis of mono- and diaryloxylated benzoic acids.

[18F]/19F exchange in fluorine containing compounds for potential use in 18F-labelling strategies

Exchange of [18F]fluoride with 19F in various organofluorine compounds in concentrations ranging from 0.06 to 56 mM was explored. We aimed to explore whether exchange reactions can be a potential useful labelling strategy, when there are no requirement of high specific radioactivity. Parameters such as solvents, temperature, conventional vs microwave heating, and the degree of fluorine load in some aromatic and alkyl compounds were investigated with regard to radiochemical yield and specific radioactivity. A series of fluorobenzophenones (1-6), 1-(4-fluorophenyl)ethanone (7), various activated and deactivated fluoro benzenes (8-16), N-(pentafluorophenyl)benzamide (17), (pentafluorophenyl)formamide (18), (tridecafluorohexyl)benzene (19) and tetradecafluorohexane (20) were subjected to [18F]/19F exchange. To test this strategy to label biologically active molecules containing fluorine atoms in an aryl group, two analogues of WAY-100635 (21-22), Lapatinib (23), 2,5,6,7,8-pentafluoro-3- methylnaphthoquinone (24) and 1-(2,4-difluorophenyl)-3-(4-fluorophenyl)-propan- 1-one (25) were investigated. The multi-fluorinated molecules containing an electron-withdrawing group were successfully labelled at room temperature, whereas the monofluorinated, as well as those containing an electron-donating group, required heating for the exchange reaction to take place. Copyright

Reactions of N-(perfluorophenyl)carbonimidoyl dichloride with aromatic acids and their derivatives in the presence of AlCl3. Formation of 2-(perfluorophenyl)isoindoline-1,3-dione and its derivatives

Reactions of N-(perfluorophenyl)carbonimidoyl dichloride with benzoic acid, benzoyl chloride, ethyl benzoate, and also with phthalic acid, phthaloyl dichloride, and phthalic anhydride in the presence of AlCl3 at 170°C afford2-(perfluorophenyl)isoindoline-1,3-dione. With benzoic acid and benzoyl chloride form also 2-(perfluorophenyl)-3-[(perfluorophenyl)imino] isoindolin-1-one. In reactions with compounds of the benzene series arise also derivatives of arylimidoyl chlorides and amide type compounds containing a CONHC6F5 moiety. 2005 Pleiades Publishing, Inc.

Quantitative determination of intermolecular interactions with fluorinated aromatic rings

The chemical double mutant cycle approach has been used to investigate substituent effects on intermolecular interactions between aromatic rings and pentafluorophenyl π-systems. The complexes have been characterised using 1H and 19F