5157-58-4

Upstream product

• 321-36-8 2,2,2-trichloro-1-(4-fluorophenyl)ethan-1-one 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 64-19-7 acetic acid 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 671188-82-2 3-(4-fluorophenyl)-3-oxopropanamide 
• 4640-67-9 3-(4-fluorophenyl)-3-oxopropionitrile 
• 451-46-7 4-fluorobenzoic acid ethyl ester 
• 456-22-4 4-Fluorobenzoic acid 
• 79-36-7 dichloroacethyl chloride 
• 462-06-6 fluorobenzene 
• 75175-77-8 3-(dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-one 
• 582-65-0 1-(4-fluorophenyl)-4,4,4-trifluoro-1,3-butanedione 

Downstream Products

• 108791-65-7 1,4‐bis(4‐fluorophenyl)butane‐1,4‐dione 
• 725-38-2 N-benzyl-4-fluorobenzamide 
• 16664-09-8 4-fluorobenzoyl azide 
• 1613145-24-6 (4-fluorophenyl)carbamoyl azide 

Relevant academic research and scientific papers

Access to α,α-dihaloacetophenones through anodic C[dbnd]C bond cleavage in enaminones

We have developed a method to synthesize α,α-dihaloketones under electrochemical conditions. In this reaction, the Cl- or Br- is oxidized to Cl2 or Br2 at the anode, which undergoes two-step addition reactions with the N,N-dimethyl enaminone, and finally breaks C[dbnd]C of the N,N-dimethyl enaminone to generate α,α-dihaloketones. The electrosynthesis reaction can be conveniently carried out in an undivided electrolytic cell at room temperature. In addition, various functional groups are compatible with this green protocol which can be applied simultaneously to the gram scale without significantly lower yield.

Electrochemical Oxidative Oxydihalogenation of Alkynes for the Synthesis of α,α-Dihaloketones

An electrochemical oxydihalogenation of alkynes has been developed for the first time. Using this sustainable protocol, a variety of α,α-dihaloketones can be prepared with readily available CHCl3, CH2Cl2, ClCH2CH2Cl, and CH2Br2 as the halogen source under electrochemical conditions at room temperature.

Electrochemical synthesis of α,α-dihaloacetophenones from terminal alkyne derivatives

By virtue of electrochemistry, a series of α,α-dihaloacetophenones were easily obtained with good to excellent yields. This electrochemical procedure was taken in a divided cell with constant current in aqueous media. The reaction can be carried out smoothly at room temperature under metal and oxidant free condition, which provides an eco-friendly synthesis for the α,α-dihaloacetophenone derivatives.

Iodine-DMSO-promoted divergent reactivities of arylacetylenes

An unprecedented set of efficient, economical, atom-economic and exceedingly selective I2-DMSO-promoted methods is described for the generation of different structures. The reaction represents the first of its kind, involving the use of different iodine concentrations, temperatures, acids and salt to adjust the selectivity for the synthesis of different alkenes, α-functionalized ketones and α-ketomethylthioesters.

Micelle-Enabled Photoassisted Selective Oxyhalogenation of Alkynes in Water under Mild Conditions

Using micelles of FI-750-M, visible light, photocatalysts, and inexpensive halogenating reagents, such as N-bromosuccinimide and N-chlorosuccinimde, selective oxyhalogenations of alkynes were achieved in water under very mild conditions. No halogenation at the aromatic rings was detected, and control experiments revealed the radical pathway. The easily conducted protocol exhibited high reproducibility, was readily adjusted to gram scale, and allowed for recycling of reaction medium and catalyst.

Dichloroacetophenones targeting at pyruvate dehydrogenase kinase 1 with improved selectivity and antiproliferative activity: Synthesis and structure-activity relationships

Dichloroacetophenone is a pyruvate dehydrogenase kinase 1 (PDK1) inhibitor with suboptimal kinase selectivity. Herein, we report the synthesis and biological evaluation of a series of novel dichloroacetophenones. Structure-activity relationship analyses (SARs) enabled us to identify three potent compounds, namely 54, 55, and 64, which inhibited PDK1 function, activated pyruvate dehydrogenase complex, and reduced the proliferation of NCI-H1975 cells. Mitochondrial bioenergetics assay suggested that 54, 55, and 64 enhanced the oxidative phosphorylation in cancer cells, which might contribute to the observed anti-proliferation effects. Collectively, these results suggested that 54, 55, and 64 could be promising compounds for the development of potent PDK1 inhibitors.

Pathways in the Degradation of Geminal Diazides

The degradation of geminal diazides is described. We show that diazido acetates are converted into tetrazoles through the treatment with bases. The reaction of dichloro ketones with azide anions provides acyl azides, through in situ formation of diazido ketones. We present experimental and theoretical evidence that both fragmentations may involve the generation of acyl cyanide intermediates. The controlled degradation of terminal alkynes into amides (by loss of one carbon) or ureas (by loss of two carbons) is also shown.

Ultrasound-assisted tandem reaction of alkynes and trihaloisocyanuric acids by thiourea as catalyst in water

With water as the sole solvent, a green and efficient method has been developed for the synthesis of various α,α-dihaloketones via ultrasound assisted p-tolylthiourea catalyzed tandem reaction of alkynes with trihaloisocyanuric acids. This synthetic route

Method for removal of methanamide by dichlorination

A method for removal of methanamide by dichlorination is disclosed, according to the method, a finished product is obtained by removal of methanamide by dichlorination by one-step-reaction of various beta-carbonyl amide derivatives as raw materials, 2,2,6,6-Tetramethylpiperidinooxy (TEMPO) and an alkali as additives and N-chlorosuccinimide as a reagent in a reaction solvent, and then concentration and purification. According to the method, synthesis of an alpha-dichloroacetophenone derivative can be realized for the first time by a method of removal of methanamide by fracturation of carbon-carbon single bond. The method is novel and unique, has certain universality, is mild in reaction conditions, low in requirement of production equipment, and simple in technology, has the advantages of high efficiency, simple operation, high safety, economy and environmentally-friendliness; high-quality diverse alpha-dichloroacetophenone derivative products can be prepared by the method, and the products prepared by the method are important drug synthesis intermediates and material intermediates, can be widely used in the synthesis of heterocycles, unsaturated acids, acetylene alcohols and other compounds and cyclopropanation, and have wide market prospects.

One-pot dichlorinative deamidation of primary β-ketoamides

An approach to the dichlorinative deamidation of primary β-ketoamides through ketonic cleavage is described, and a series of α,α-dichloroketones were furnished mostly in the presence of TEMPO. Based on control experiments, a mechanism involving tandem dichlorination and deamidation is proposed to interpret the observed reactivity.