16473-39-5

Upstream product

• 104-93-8 p-methylanizole 
• 1415115-16-0 C₁₃H₁₂FNO₃S 
• 1365765-67-8 2-fluoro-1-(4-methoxyphenyl)-2-(pyridin-2-ylsulfonyl)ethanone 
• 696-62-8 para-iodoanisole 
• 824-94-2 p-methoxybenzyl chloride 
• 2746-25-0 p-Methoxybenzyl bromide 
• 373-53-5 fluoroiodomethane 
• 171364-79-7 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 5720-07-0 4-methoxyphenylboronic acid 
• 29180-19-6 4-methoxybenzyl carbocation 
• 105-13-5 4-Methoxybenzyl alcohol 
• 2393-23-9 4-methoxy-benzylamine 
• 101803-60-5 tert-butyl((4-methoxybenzyl)oxy)dimethylsilane 
• 14629-56-2 trimethyl(4-methoxybenzyloxy)silane 

Downstream Products

• 105-13-5 4-Methoxybenzyl alcohol 

Relevant academic research and scientific papers

Metal-free reduction of the greenhouse gas sulfur hexafluoride, formation of SF5 containing ion pairs and the application in fluorinations

A protocol for the fast and selective two-electron reduction of the potent greenhouse gas sulfur hexafluoride (SF6) by organic electron donors at ambient temperature has been developed. The reaction yields solid ion pairs consisting of donor di

Solvent free nucleophilic introduction of fluorine with [bmim][F]

1-n-Butyl-3-methylimidazolium fluoride ([bmim][F]) proved very efficient fluorinated reagent for nucleophilic substitution over sulfonate esters and alkyl halides. Preparation of the ionic liquid as well as its use as the reagent has been performed to be the more eco-friendly as possible. No organic solvent is needed for the fluoride introduction, reaction times are reduced by using microwave as the heating source, and the ionic liquids carefully recycled. Furthermore, no special care has to be taken as the presence of water in [bmim][F] was not deleterious to the transformation yield.

METHOD AND REAGENT FOR DEOXYFLUORINATION

A safe, simple, and selective method and reagent for deoxyfluorination is disclosed. With the method and reagent disclosed herein, organic compounds such as carboxylic acids, carboxylates, carboxylic acid anhydrides, aldehydes, and alcohols can be fluorinated by using the most common nucleophilic fluorinating reagents and electron deficient fluoroarenes as mediators under mild conditions, giving corresponding fluoroorganic compounds in excellent yield with a wide range of functional group compatibility and easy product purification. For example, directly utilizing KF for deoxyfluorination of carboxylic acids provides the most economical and the safest pathway to access acyl fluorides, key intermediates for syntheses of peptide, amide, ester, and dry fluoride salts.

A Series of Deoxyfluorination Reagents Featuring OCF2Functional Groups

Research on perfluoroalkyl ether carboxylic acids (PFECAs) as alternatives for perfluoroalkyl substances continues with the goal of protecting the environment. However, very little is known about the utilization of decomposition products of PFECAs. We report herein a new series of deoxyfluorination reagents featuring OCF2 functional groups derived from certain PFECAs. Alkyl fluorides were generated from various alcohols in ≤97% yield by these novel reagents. The mechanistic experiment verified in situ generation of carbonic difluoride (COF2).

Fluorination reagent and deoxygenation fluorination method

In order to overcome the problems of high cost and poor stability of the existing deoxidation fluorination reagent, the invention provides a fluorination reagent. The fluorination reagent comprises acation M and an anion, and the anion is selected from one or more of the following perfluoropolyether chain carboxylic acid anions: CF3 (OCF2) nCO2, and n is selected from 1-10. Meanwhile, the invention further discloses a deoxidation fluorination method. The fluorination reagent provided by the invention has the advantages that the materials are easy to obtain, the fluorination products can beobtained at higher yield for various alcohol substrates, and the universality for different alcohol substrates is better.

Palladium-Catalyzed Monofluoromethylation of Arylboronic Esters with Fluoromethyl Iodide

The first palladium-catalyzed direct monofluoromethylation of arylboronic esters to produce monofluoromethyl arenes is reported. The reaction is typically carried out at room temperature within 4 h and has a good functional group tolerance. The monofluoromethylating agent, CH2FI, was readily prepared via a halogen-exchange process.

Nickel-catalyzed monofluoromethylation of aryl boronic acids

Aryl boronic acids can be monofluoromethylated under nickel catalysis. The utility of this method is demonstrated by the monofluoromethylation of a borylated and acyl-protected derivative of the statin drug ezetimibe. Mechanistic investigations indicate that a fluoromethyl radical is involved in the NiI/NiIII catalytic cycle.

Friedel-crafts reaction of benzyl fluorides: Selective activation of C-f bonds as enabled by hydrogen bonding

A Friedel-Crafts benzylation of arenes with benzyl fluorides has been developed. The reaction produces 1,1-diaryl alkanes in good yield under mild conditions without the need for a transition metal or a strong Lewis acid. A mechanism involving activation of the C-F bond through hydrogen bonding is proposed. This mode of activation enables the selective reaction of benzylic C-F bonds in the presence of other benzylic leaving groups.

Copper-catalyzed debenzoylative monofluoromethylation of aryl iodides assisted by the removable (2-Pyridyl)sulfonyl group

A new method for aromatic monofluoromethylation was developed. Aryl iodides can be efficiently transformed into the corresponding monofluoromethylated products by a copper-catalyzed debenzoylative fluoroalkylation with 2-PySO 2CHFCOR and subsequent reductive desulfonylation. The (2-pyridyl)sulfonyl moiety plays an important role in the copper-catalyzed cross-coupling, and it can be removed easily through Bu3SnH-mediated desulfonylation.

Fluorination reactions in microreactors

The DAST-mediated conversion of a range of alcohols to the corresponding fluorides in a microstructured device is described. This safe, practical fluorination method will facilitate reactions currently challenging on large scale. The Royal Society of Chem