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Iron-Catalyzed, Fluoroamide-Directed C–H Fluorination

Author:
Groendyke, Brian J., AbuSalim, Deyaa I., Cook, Silas P.
Source:
Journal of the American Chemical Society 2016 v.138 no.39 pp. 12771-12774
ISSN:
1520-5126
Subject:
additives, chemical bonding, fluorides, fluorine, iron
Abstract:
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.
Agid:
5560556