156335-24-9

Upstream product

• 403-30-5 1-(4-bromophenyl)-2-fluoroethan-1-one 
• 99-73-0 para-bromophenacyl bromide 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 32017-76-8 (+/-)-2-(4-bromophenyl)oxirane 

Downstream Products

• 1073056-16-2 (S)-1-(4-bromophenyl)-2-fluoroethyl benzoate 

Relevant academic research and scientific papers

Enantioselective radiosynthesis of positron emission tomography (PET) tracers containing [18F]fluorohydrins

Herein, we describe an operationally straightforward radiosynthesis of a chiral transition metal fluoride catalyst, [18F](salen)CoF, and its use for late-stage enantioselective aliphatic radiofluorination. We demonstrate the utility of the method by preparing single enantiomer experimental and clinically validated PET tracers that contain base-sensitive functional groups, epimerizable stereocenters, and nitrogen-rich motifs. Unlike the conventional radiosyntheses of these targets with [18F]KF, labeling with (salen)CoF is possible in the last step and under exceptionally mild conditions. These results constitute a rare example of a nucleophilic radiofluorination using a transition metal fluoride and highlight the potential of such reagents to enhance traditional methods for labeling aliphatic hydrocarbons.

Synthesis of enantiopure fluorohydrins using alcohol dehydrogenases at high substrate concentrations

The use of purified and overexpressed alcohol dehydrogenases to synthesize enantiopure fluorinated alcohols is shown. When the bioreductions were performed with ADH-A from Rhodococcus ruber overexpressed in E. coli, no external cofactor was necessary to obtain the enantiopure (R)-derivatives. Employing Lactobacillus brevis ADH, it was possible to achieve the synthesis of enantiopure (S)-fluorohydrins at a 0.5 M substrate concentration. Furthermore, due to the activated character of these substrates, a huge excess of the hydrogen donor was not necessary.

Palladium-catalyzed intermolecular fluoroesterification of styrenes: Exploration and mechanistic insight

A novel palladium-catalyzed intermolecular oxidative fluoroesterification of vinylarenes has been developed using NFSI, one of the mildest electrophilic fluorinating reagents. The reaction presents an efficient synthetic pathway to afford a series of α-monofluoromethylbenzyl carboxylates in good to excellent yields. Rather than following an electrophilic fluorination pathway, the reaction is initiated through oxidation of Pd(0) to a Pd(ii) fluoride complex by NFSI, followed by fluoropalladation of a styrene to generate an α-monofluoromethylbenzyl-Pd intermediate. Generally, reductive elimination of benzyl-PdII complexes is favored with relatively strong oxy-nucleophiles to afford C-O bonds. This reaction, however, exhibited the opposite reactivity: strong acids with weak nucleophilicity, such as CF 3CO2H and CCl3CO2H, were prone to afford the fluoroesterification product, while weak acids with strong nucleophilicity, such as HOAc and BzOH, did not deliver the C-O bond product. Further mechanistic studies determined that Csp3-Pd(O2CR), a key intermediate, was generated through ionic ligand exchange between benzyl-Pd(NZ2) and CF3CO2H, and the final C-O bond was possibly formed through reductive elimination of a high-valent Csp 3-Pd(O2CR) complex via an SN2-type nucleophilic attack pathway.

Asymmetric reduction using (R)-MeCBS and determination of absolute configuration of para-substituted 2-fluoroarylethanols

The asymmetric reduction of eight α-fluoroacetophenones has been investigated using (R)-MeCBS as a catalyst in various media. Based on a solvent screen, 1,2-dimethoxyethane, diethyl ether and dichloromethane were used in reductions of the α-fluoroacetophe

Conformational Analysis. Part 22. An NMR and Theoretical Investigation of the gauche Effect in Fluoroethanols

The ABCX NMR spectrum of the C*CH(OH)*CH2F fragment of 1-(4-bromophenyl)-2-fluoroethanol (BPFE) in eight solvents of different polarities was recorded and fully analysed. 13C and NOE measurements confirmed the assignment of the prochiral methylene protons