Fluorobis(phenylsulfonyl)methane (FBSM)

Introduction

Given the growing importance of fluorinated molecules in medicinal chemistry and chemical biology, several researchers are investigating the methods for the incorporation of fluorine into drug candidates since fluorine-containing compounds can have positive effects on the pharmacological properties of a drug. One of the most convenient ways to construct fluorine-containing organic molecules asymmetrically is the utilization of fluorobis(phenylsulfonyl)methane (FBSM), which has recently been introduced by Shibata and Hu, independently.[1] FBSM is a colorless solid, stable in air, and easily handled. It can readily be synthesized from fluoromethyl phenyl sulfone and benzenesulfonyl fluoride (Scheme [1]).[2]

Recently, FBSM has widely been used as a potential monofluoromethide equivalent in synthetic organic transformations. For example, structurally diverse monofluorobis(phenylsulfonyl)methylated chiral adducts containing a hydroxyl-/or amino group are synthesized by means of asymmetric enamine, iminium, phase-transfer, and cooperative catalysis concepts. In particular, further reductive desulfonylation of the previous adducts can be accompanied by treatment with Mg-MeOH to give monofluoromethylated products in high yield, while keeping their enantioselectivity.

Scheme 1 Preparation of FBSM.

• References

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