135359-29-4

Upstream product

• 135359-37-4 (Z)-2-Fluoro-4-phenyl-but-2-enoic acid ethyl ester 
• 100420-10-8 4-phenyl-1-(pyrrolidin-1-yl)butan-1-one 
• 93921-85-8 ethyl 2-hydroxy-4-phenylbutanoate 
• 100-42-5 styrene 
• 401-55-8 ethyl bromofluoroacetate 
• 6628-68-8 ethyl 2-(ethoxycarbonyl)-4-phenylbutanoate 

Downstream Products

• 1616365-93-5 (3-bromo-3-fluoropropyl)benzene 
• 587853-65-4 4-fluoro-1-tetralone 

Relevant academic research and scientific papers

α-Fluorination of carbonyls with nucleophilic fluorine

Given the unique properties of fluorine, and the ability of fluorination to change the properties of organic molecules, there is significant interest from medicinal chemists in innovative methodologies that enable the synthesis of new fluorinated motifs. State-of-the-art syntheses of α-fluorinated carbonyl compounds invariably rely on electrophilic fluorinating agents, which can be strongly oxidizing and difficult to handle. Here we show that reversing the polarity of the enolate partner to that of an enolonium enables nucleophilic fluorinating agents to be used for direct chemoselective α-C–H-fluorination of amides. Reduction of these products enables facile access to β-fluorinated amines and the value of this methodology is shown by the easy preparation of a number of fluorinated analogues of drugs and agrochemicals. A fluorinated analogue of citalopram, a marketed antidepressant drug, is presented as an example of the preserved biological activity after fluorination.

Irradiation-Induced Cobaloxime-Catalyzed C-H Monofluoroalkylation of Styrenes at Room Temperature

A cobaloxime-catalyzed photochemical synthesis of allyl monofluorides from styrenes is described herein. This method is characterized by mild reaction conditions, low-cost catalyst, and broad substrate scope. Furthermore, this convenient method will provide a facile synthesis toward novel monofluoroalkylated natural product and pharmaceutical derivatives. Mechanistic investigations indicate that a monofluoroalkyl radical is involved in the catalytic cycle.

Deoxyfluorination of alcohols with aryl fluorosulfonates

Aryl fluorosulfonates are developed as a deoxyfluorinating reagent in the transformation of primary and secondary alcohols into the corresponding alkyl fluorides. These reagents feature easy availability, low-cost, high stability and high efficiency. Diverse functionalities including aldehyde, ketone, ester, halogen, nitro, alkene, and alkyne are well tolerated under mild reaction conditions.

A diastereoselective Mannich-type reaction of α-fluorinated carboxylate esters: Synthesis of β-amino acids containing α-quaternary fluorinated carbon centers

We report a diastereoselective Mannich-type reaction of α-alkyl, α-aryl, and α-vinyl fluoroacetates with N-tert-butylsulfinyl imines. This method provides a powerful means to access a broad range of highly functionalized β-amino acids containing α-fluorinated quaternary stereogenic carbon centers. We also show that the stereochemical outcome of the present reaction is highly dependent on the steric and electronic properties of the fluorocarbon nucleophiles. This protocol uses readily available starting materials, tolerates a variety of functional groups, and is operationally simple.

Enantioselective Suzuki cross-couplings of unactivated 1-fluoro-1-haloalkanes: Synthesis of chiral β-, γ-, δ-, and ε-fluoroalkanes

The incorporation of fluorine atom into a stereogenic center is a highly challenging transformation with current methodologies offering access mainly to chiral α- and β-fluoroalkanes. In this article, the development of a novel general approach to constru

The hydrogenation of fluoroolefins

Palladium catalysts are found to selectively hydrogenate fluoroolefins without hydrogenolytic cleavage of the carbon-fluorine bond. Since a large number of methods are available for the preparation of unsaturated organofluoro compounds this constitutes a general synthetic route to sp3-fluorinated molecules.