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Title: N-Directed fluorination of unactivated Csp 3 –H bonds
Site-selective fluorination of aliphatic C–H bonds remains synthetically challenging. While directed C–H fluorination represents the most promising approach, the limited work conducted to date has enabled just a few functional groups as the arbiters of direction. Leveraging insights gained from both computations and experimentation, we enabled the use of the ubiquitous amine functional group as a handle for the directed C–H fluorination of Csp 3 –H bonds. By converting primary amines to adamantoyl-based fluoroamides, site-selective C–H fluorination proceeds under the influence of a simple iron catalyst in 20 minutes. Computational studies revealed a unique reaction coordinate for the catalytic process and offer an explanation for the high site selectivity.  more » « less
Award ID(s):
1726633
NSF-PAR ID:
10183006
Author(s) / Creator(s):
; ; ;
Date Published:
Journal Name:
Chemical Science
Volume:
11
Issue:
4
ISSN:
2041-6520
Page Range / eLocation ID:
1102 to 1106
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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