Selectfluor: mechanistic insight and applications.
The replacement of hydrogen atoms with fluorine substituents in organic substrates is of great interest in synthetic chemistry because of the strong electronegativity of fluorine and relatively small steric footprint of fluorine atoms. Many sources of nucleophilic fluorine are available for the derivatization of organic molecules under acidic, basic, and neutral conditions. However, electrophilic fluorination has historically required molecular fluorine, whose notorious toxicity and explosive tendencies limit its application in research. The necessity for an electrophilic fluorination reagent that is safe, stable, highly reactive, and amenable to industrial production as an alternative to very hazardous molecular fluorine was the inspiration for the discovery of selectfluor. This reagent is not only one of the most reactive electrophilic fluorinating reagents available, but it is also safe, nontoxic, and easy to handle. In this Review we document the many applications of selectfluor and discuss possible mechanistic pathways for its reaction.
Nyffeler
Paul T
PT
Department of Chemistry and Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, BCC 357, La Jolla, California 92037, USA.
Durón
Sergio Gonzalez
SG
Burkart
Michael D
MD
Vincent
Stéphane P
SP
Wong
Chi-Huey
CH
D003979:Diazonium Compounds / Q000737:chemistry*; D004583:Electrons; D005461:Fluorine / Q000737:chemistry*; D013237:Stereoisomerism
D003979:Diazonium Compounds; D005461:Fluorine; C408750:selectfluor