Direct photocatalytic fluorination of benzylic C-H bonds with N-fluorobenzenesulfonimide

The late-stage fluorination of common synthetic building blocks and drug leads is an appealing reaction for medicinal chemistry. In particular, fluorination of benzylic C-H bonds provides a means to attenuate drug metabolism at this metabolically labile position. Here we report two complimentary str...

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Bibliographic Details
Published in:	Chemical communications (Cambridge, England) Vol. 51; no. 59; p. 11783
Main Authors:	Nodwell, Matthew B, Bagai, Abhimanyu, Halperin, Shira D, Martin, Rainer E, Knust, Henner, Britton, Robert
Format:	Journal Article
Language:	English
Published:	England 28-07-2015
Subjects:	Benzyl Compounds - chemistry Catalysis Hydrocarbons, Fluorinated - chemical synthesis Hydrocarbons, Fluorinated - chemistry Molecular Structure Photochemical Processes Sulfonamides - chemistry
Online Access:	Get more information
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Summary:	The late-stage fluorination of common synthetic building blocks and drug leads is an appealing reaction for medicinal chemistry. In particular, fluorination of benzylic C-H bonds provides a means to attenuate drug metabolism at this metabolically labile position. Here we report two complimentary strategies for the direct fluorination of benzylic C-H bonds using N-fluorobenzenesulfonimide and either a decatungstate photocatalyst or AIBN-initiation.
ISSN:	1364-548X
DOI:	10.1039/c5cc04058b