N-Directed fluorination of unactivated Csp3–H bonds

文献情報

出版日 2019-12-16

DOI 10.1039/C9SC04055B

インパクトファクター 9.825

著者

Emily N. Pinter, Jenna E. Bingham, Deyaa I. AbuSalim, Silas P. Cook

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要旨

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.

掲載誌

Chemical Science

CiteScore: 14.4

自己引用率: 3.9%

年間論文数: 1413

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N-Directed fluorination of unactivated Csp3–H bonds

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