N-Directed fluorination of unactivated Csp3–H bonds
Literature Information
Publication Date
2019-12-16
DOI
10.1039/C9SC04055B
Impact Factor
9.825
Authors
Emily N. Pinter, Jenna E. Bingham, Deyaa I. AbuSalim, Silas P. Cook
View Original
Abstract
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.
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