1295-38-1

Upstream product

• 226882-93-5 ferrocene carboxylic acid fluoride 
• 108-95-2 phenol 
• 403819-33-0 1-ferrocenoyl-1H-imidazole 
• 139-02-6 sodium phenoxide 
• 1163726-65-5 1-(ferrocenylcarbonyl)-1H-benzotriazole 
• 1293-79-4 ferrocenoyl chloride 
• 12093-10-6 ferrocenecarboxaldehyde 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters

The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]

Functionalized ferrocenes: The role of the para substituent on the phenoxy pendant group

Six ferrocenecarboxylates with phenyl, 4-(1H-pyrrol-1-yl)phenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl as pendant groups were synthesized and fully characterized by spectroscopic, electrochemical and X-ray diffraction methods. The anti-proliferative activity of these complexes were investigated in hormone dependent MCF-7 breast cancer and MCF-10A normal breast cell lines, to determine the role of the para substituent on the phenoxy pendant group. The 4-fluorophenyl ferrocenecarboxylate is inactive in both cell lines while 4-(1H-pyrrol-1-yl)phenyl ferrocenecarboxylate is highly cytotoxic in both cell lines. 4-chlorophenyl and 4-bromophenyl ferrocenecarboxylates have moderate to good anti-proliferative activity in MCF-7 and low anti-proliferative activity on normal breast cell line, MCF-10A whereas the 4-iodophenyl analog is highly toxic on normal breast cell line. The phenyl ferrocenecarboxylate has proliferative effects on MCF-7 and is inactive in MCF-10A. Docking studies between the complexes and the alpha-estrogen receptor (ERα) were performed to search for key interactions which may explain the anti-proliferative activity of 4-bromophenyl ferrocenecarboxylate. Docking studies suggest the anti-proliferative activity of these ferrocenecarboxylates is attributed to the cytotoxic effects of the ferrocene group and not to anti-estrogenic effects.

N-Heterocyclic carbene catalysed aerobic oxidation of aromatic aldehydes to aryl esters using boronic acids

The organocatalytic behavior of N-heterocyclic carbenes in the aerobic oxidation of aromatic aldehydes to esters with boronic acids has been explored. This transition metal-free protocol allows access to a wide variety of aromatic esters in good to excellent yields under mild reaction conditions.

N-ferrocenoyl benzotriazole: A convenient tool for the synthesis of ferrocenoyl esters

A new synthesis methodology has been presented for the preparation of the ferrocenoyl esters. Ferrocene carboxylic acid was derivatized using direct 1H-benzotriazole/SOCl2 methodology to prepare N-ferrocenoyl benzotriazole as a convenient tool for the functionalization of ferrocene ring. N-ferrocenoyl benzotriazole was reacted with alcohols in mild conditions to prepare ferrocenoyl esters in high purity and in good yield. The solid state structure of benzyl-1-ferrocenoate, 2f, has also been determined by X-ray crystallography. In the crystal structure, intermolecular C-H···O hydrogen bonds link the molecules into a two-dimensional network. The π···π contacts between the cyclopentadiene rings and cyclopentadiene and phenyl rings, [centroid-centroid distances = 3.296(1) and 3.750(1) A?] may further stabilize the structure. Two weak C-H···π interactions are also found.

Synthesis of ferrocenoate esters, amides and other ferrocenoyl derivatives using ferrocenoyl fluoride. A comparison of the reactions of ferrocenoyl fluoride in [bmim][BF4] with the microwave-promoted solvent-free reactions of ferrocenoyl fluoride

Simple, efficient and convenient routes for the synthesis of ferrocenoyl derivatives are described. They involve either the reaction of nucleophilic compounds and DMAP with ferrocenoyl fluoride in [bmim][BF4] or the solvent-free reactions of nucleophilic compounds with ferrocenoyl fluoride promoted by microwaves.

An investigation of the chemistry of ferrocenoyl derivatives. The synthesis and reactions of ferrocenoyl imidazolide and its derivatives

Ferrocenoyl imidazolide is synthesized readily from ferrocenecarboxylic acid in one step. It is a red crystalline compound that is stable at 5°C in the dark and it acts as an efficient ferrocenoyl equivalent. It reacts rapidly with alkoxides to give esters and with thiolates to give thioesters. Its reaction with Lawesson's reagent gave diferrocenoyl disulfide. Attempts to make diferrocenoyl peroxide by reacting ferrocenoyl imidazolide with hydrogen peroxide were unsuccessful. Ferrocenoyl imidazolide is converted into triferrocenylmethanol and diferrocenyl ketone in one step by reacting it with ferrocenyl-lithium. The X-ray crystal structures of ferrocenoyl phenyl sulfide and diferrocenoyl disulfide are described.