The introduction of fluoromethyl group(-CH2F) into organic molecules has recently attracted much attention in organic synthesis, owing to the increasingly important applications of selectively fluorinated compounds in life science. For instance,the fluorinated functional group with α-fluorinated carbanions have been used as oxygen mimics in molecules such as nucleotides, phosphate esters and sulphate esters. Compounds with a monofluoromethyl group are of great importance with regard to isostere-based drug design. As a result, some structurally diverse CH2F-containing drugs have already been developed. One representative example is the drug named Fluoticasone propionate,which is widely used against inflammatory diseases and to alleviate pains associated with certain cancers.
Selective fluoromethylation are generally accomplished by two strategies: one is the direct transfer of a "CH2F" moiety into organic molecules; the other is the transfer of a functionalized moiety( such as "CFR2"), followed by removal of the functional or auxiliary group(s) to give a CH2F group. Both these above-mentioned two strategies can be further realised in nucleophilic, electrophilic and radical methods as followed:
1. Electrophilic Fluoromethylation: Reactive nucleophiles and fluoromethylating reagents with good leaving groups are normally required for electrophilic fluoromethylation.The S-(monofluoromethyl)diarylsulfonium tetrafluoroborate (kumi5F05) has been reported to be effective for the introduction of an electrophilic monofluoromethyl group into C,S,O,N,and P nucleophiles; Further more, this fluoromethylsulfonium reagent was expanded for the synthesis of various biologically important compounds.
2. Nucleophilic Fluoromethylation: The electrophiles for nucleophilic fluoromethylation relies on the use of fluoromethide equivalents, typically containing mesomeric stabilizing groups such as sulfones. A general approach to nucleophilic fluoromethylation involves electrophiles bearing electron-withdrawing group-stablized fluoromethide equivalents generated by deprotonation of pronucleophiles. In 2006, Hu and coworkers reported the efficient monofluoromethylation of imines using fluoromethyl phenyl sulfone (PhSO2CH2F,kumi1F08) and the reactions resulted in high stereoselectivity. Another reagent, fluorobis(phenylsulfonyl)methane (FBSM,kumi1F09), was synthesized independently by Hu and Shibata it the same year, which can transfer CH2F group to epoxides and α,β- unsaturated ketones, respectively.
3. Radical Fluoromethylation: The free radical of CH2F group is much less stable than its analogous CF3 and CF2H group. Although few, some examples of radical fluoromethylation have been reported. Hu and his group recently demonstrated the utility of Sodium fluoromethanesulfinate(kumi1F03) as efficient radical fluoroalkylating reagents able to react with conjugated N-arylsulfonated amides to yield the desired fluoroalkylamides.
Fluoromethylating Reagents Overview
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