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N-Directed fluorination of unactivated Csp3–H bonds

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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.

Graphical abstract: N-Directed fluorination of unactivated Csp3–H bonds

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Article information


Submitted
14 Aug 2019
Accepted
27 Nov 2019
First published
16 Dec 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

N-Directed fluorination of unactivated Csp3–H bonds

E. N. Pinter, J. E. Bingham, D. I. AbuSalim and S. P. Cook, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC04055B

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