N-Directed fluorination of unactivated Csp3–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...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2020-01, Vol.11 (4), p.1102-1106
Main Authors: Pinter, Emily N, Bingham, Jenna E, AbuSalim, Deyaa I, Cook, Silas P
Format: Article
Language:English
Subjects:
Aliphatic compounds
Amines
Bonding
Chemistry
Experimentation
Fluorination
Functional groups
Selectivity
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Summary: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 Csp3–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.
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc04055b