772-67-8

Upstream product

• 3277-89-2 phenethylmagnesium bromide 
• 459-72-3 ethyl 2-fluoroacetate 
• 503-20-8 fluoroacetonitrile 
• 103-63-9 1-phenyl-2-bromoethane 
• 1035814-78-8 1-fluoro-4-phenylbutan-2-ol 
• 373-53-5 fluoroiodomethane 
• 170646-96-5 N-methoxy-N-methyl-3-phenylpropionamide 
• 645-45-4 hydrocinnamic acid chloride 
• 100-39-0 benzyl bromide 
• 114156-08-0 fluoroacetone cyclohexylimine 
• 99687-73-7 fluoroacetone cyclohexylimine 

Downstream Products

• 1541177-56-3 1-fluoro-4-phenyl-2-((trimethylsilyl)methyl)butan-2-ol 
• 1415314-84-9 C₁₄H₁₇FO₂ 
• 1415314-89-4 C₁₂H₁₅FO 
• 1415315-19-3 C₁₄H₁₉F 
• 110229-72-6 Acetic acid 1-fluoromethyl-3-phenyl-propyl ester 
• 1035814-78-8 1-fluoro-4-phenylbutan-2-ol 

Relevant academic research and scientific papers

Fluoro-Substituted Methyllithium Chemistry: External Quenching Method Using Flow Microreactors

The external quenching method based on flow microreactors allows the generation and use of short-lived fluoro-substituted methyllithium reagents, such as fluoromethyllithium, fluoroiodomethyllithium, and fluoroiodostannylmethyllithium. Highly chemoselective reactions have been developed, opening new opportunities in the synthesis of fluorinated molecules using fluorinated organometallics.

Exploiting a beast in carbenoid chemistry: Development of a straightforward direct nucleophilic fluoromethylation strategy

The first direct and straightforward nucleophilic fluoromethylation of organic compounds is reported. The tactic employs a fleeting lithium fluorocarbenoid (LiCH2F) generated from commercially available fluoroiodomethane. Precise reaction conditions were developed for the generation and synthetic exploitation of such a labile species. The versatility of the strategy is showcased in ca. 50 examples involving a plethora of electrophiles. Highly valuable chemicals such as fluoroalcohols, fluoroamines, and fluoromethylated oxygenated heterocycles could be prepared in very good yields through a single synthetic operation. The scalability of the reaction and its application to complex molecular architectures (e.g., steroids) are documented.

Toward a Unified Mechanism for Oxoammonium Salt-Mediated Oxidation Reactions: A Theoretical and Experimental Study Using a Hydride Transfer Model

A range of oxoammonium salt-based oxidation reactions have been explored computationally using density functional theory (DFT), and the results have been correlated with experimentally derived trends in reactivity. Mechanistically, most reactions involve a formal hydride transfer from an activated C-H bond to the oxygen atom of the oxoammonium cation. Several new potential modes of reactivity have been uncovered and validated experimentally.

Formation of chiral fluoroalkyl products through copper-free enantioselective allylic alkylation catalyzed by an NHC ligand

A valuable Cu-free protocol is reported where an NHC ligand has been employed to form quaternary carbon centers bearing fluoroalkyl units. The results obtained, from this allylic substitution, are better in terms of enantioselectivity and regioselectivity compared to the copper catalyzed system.

Fluoro-substituted ketones from nitriles using acidic and basic reaction conditions

Fluoro-substituted aliphatic nitriles are shown to undergo the Houben-Hoesch reactions with arenes in CF3SO3H to give fluoro-substituted ketones in good yields. The fluorine substituents appear to enhance the reactivities of the nitriles (and the nitrilium ion intermediates) compared to similar aliphatic nitriles. Fluoro-substituted ketones are also shown to be accessible through the reactions of organometallic reagents and fluoro-substituted nitriles.

Homochiral α-Fluoroketones from Racemic α-Fluorocarboxylic esters and Enantiomerically Pure Sulphoxides

The α-fluoroalkyl ketones (3-7) carrying an alkyl, alkenyl, hydroxymethyl, or formyl residue were obtained in enantiomerically pure form by removing, by various methods, the auxiliary sulphinyl group from the α-fluoro α'-sulphinyl ketones (1) and (2) deri

Synthesis, Regioselective Deprotonation, and Stereoselective Alkylation of Fluoro Ketimines

Fluoroacetone imines of cyclohexylamine, valinol O-methyl ether, and phenylalaninol O-methyl ether and 2-fluorocyclohexanone imines of cyclohexylamine and phenylalaninol O-methyl ether were prepared.The temperature-dependent, regioselective deprotonation of these imines was employed in highly regioselective alkylation reactions.The deprotonation of fluoroacetone cyclohexylimine on the carbon bearing fluorine yielded only a single stereoisomer as determined by low temperature 19F NMR.In contrast, deprotonation of fluoroacetone O-benzyloximes was not regiospecific under any of the conditions examined.

The Temperature-Dependent Regioselective Deprotonation of Fluoroacetone Cyclohexylimine

The temperature-dependent regioselective deprotonation of fluoroacetone cyclohexylimine was developed as a procedure for the regioselective alkylation of fluoroacetone.