Iron-Catalyzed, Fluoroamide-Directed C-H Fluorination.
This communication describes a mild, amide-directed fluorination of benzylic, allylic, and unactivated C-H bonds mediated by iron. Upon exposure to a catalytic amount of iron(II) triflate (Fe(OTf)2), N-fluoro-2-methylbenzamides undergo chemoselective fluorine transfer to provide the corresponding fluorides in high yield. The reaction demonstrates broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic and computational experiments suggest that the reaction proceeds through short-lived radical intermediates with F-transfer mediated directly by iron.
Department of Chemistry, Indiana University , 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, United States.
Brian J
BJ
Groendyke
Department of Chemistry, Indiana University , 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, United States.
Deyaa I
DI
AbuSalim
Department of Chemistry, Indiana University , 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, United States.
Silas P
SP
Cook