1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (C15-1214-404)

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product is a fluorine donor also called Selectfluor and has been enhanced for catalysis. Find details here.

Application

1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) is an electrophilic fluorinating reagent used for greener fluorination of acetoacetamides in PEG-400.
Catalyst-free and highly selective electrophilic mono-fluorination of acetoacetamides: facile and efficient preparation of 2-fluoroacetoacetamides in PEG-400

It can be used:

• As a highly effective and versatile source of electrophilic fluorine.
• As a fluorinating reagent that effects oxidative ring opening of 2,5-diarylfurans to cis-1,4-enediones.
• For direct fluorination of silyl ketene acetals leading to the formation of α-fluoro-α-arylcarboxylic acids.
• As an electrophilic fluorinating reagent used. e.g. in the preparation of fluorinated acylsilanes.

Other Notes

First application of ionic liquids in electrophilic fluorination of arenes; Selectfluor (F-TEDA-BF4) for “green” fluorination.

Citation

A review.