Published Research - Department of Chemistry


Date of this Version



Published in Organic Letters 13:12 (2011), pp. 3158–3161; doi: 10.1021/ol201080c Copyright © 2011 American Chemical Society. Used by permission.


For the first time it is shown that exceptionally electron-rich arene rings can be fluorinated exclusively during the reductive elimination reactions of diaryliodonium fluorides. The 5-methoxy[2.2]paracyclophan-4-yl directing group simultaneously reduces unproductive aryne chemistry and eliminates ligand exchange reactions by a combination of steric and electronic effects. Use of the cyclophane directing group permits an unprecedented degree of control in fluorination reactions of diaryliodonium salts.

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