Selectfluor (F-TEDA-BF₄) C₇H₁₄B₂ClF₉N₂

Introduction

Selectfluor [1] is one of the most reactive electrophilic ­fluorinating reagents. It is a white, free-flowing, virtually non-hygroscopic, high-melting solid (mp 170 °C) [2] and is soluble in few polar solvents, e.g. MeCN, DMF, H₂O, MeNO₂, ionic liquids. It is a safe, stable, non-toxic, easy-to-handle reagent that is amenable to industrial production. It provides an alternative to molecular fluorine which is a hazardous, highly toxic, strong oxidant, with little or no specificity. [1] Selectfluor helps in the fluorination of steroidal enol acetates, [3] monofluoro ketomethylene dipeptide isosterase, [4] carbanions, and Grignard reagents, and in the α-fluorination of sulfides, [2] aldehydes and ketones. [5] Besides these properties (in two-electron processes), it also shows oxidative characteristics, and forms potent ­indium sources with molecular iodine, although it decomposes in the presence of iodide ion. It is also useful in the conversion of common anions into electrophiles. [6]

References

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