a-Fluorobis(phenylsulfonyl)methane  (FBSM) has been developed as a useful monofluoromethylating reagent in recent years. Conventional synthetic approaches toward FBSM, such as the electrophilic fluorination of bis(phenylsulfonyl)methide anion using Selectfluor�, significantly suffer from unsatisfactory chemoselectivity. Column chromatographic technique is thus inevitable and impedes large-scale preparation (usually <5 g scale). To address this synthetic challenge, our laboratory has developed a practical and scalable synthetic protocol utilizing readily available starting materials. The novel preparative method can be feasibly performed on up to 100 g scales to afford the product in almost quantitative yield. In particular, efficiently purified by simple extraction and crystallization technique, the product can be obtained in high purity without chromatography. 

Practical and scalable synthesis of α-fluorobis(phenylsulfonyl)methane as a versatile nucleophilic monofluoromethylating reagent

243rd National Meeting (2012)

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