Version 2 2016-09-30, 19:30Version 2 2016-09-30, 19:30
Version 1 2016-09-27, 16:20Version 1 2016-09-27, 16:20
journal contribution
posted on 2016-09-27, 00:00authored byBrian
J. Groendyke, Deyaa I. AbuSalim, Silas P. Cook
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.