N-Directed fluorination of unactivated Csp3-H bonds
Emily N Pinter1, Jenna E Bingham1, Deyaa I AbuSalim1
1Department of Chemistry, Indiana University 800 East Kirkwood Avenue Bloomington IN 47405-7102 USA sicook@indiana.edu.
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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