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A Convenient Photocatalytic Fluorination of Unactivated C[BOND]H Bonds

Authors


  • This work was supported by an NSERC Discovery Grant to R.B., a MSFHR Career Investigator Award to R.B., and NSERC Postgraduate Scholarships for S.D.H., H.F., S.C.

Abstract

Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site-selective metabolic degradation of drugs and access radiotracers for positron emission tomography imaging. Despite current sophistication in fluorination reagents and processes, the fluorination of unactivated C[BOND]H bonds remains a significant challenge. Reported herein is a convenient and economic process for direct fluorination of unactivated C[BOND]H bonds that exploits the hydrogen abstracting ability of a decatungstate photocatalyst in combination with the mild fluorine atom transfer reagent N-fluorobenzenesulfonimide. This operationally straightforward reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acid derivatives.

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