Unprecedented Directing Group Ability of Cyclophanes in Arene Fluorinations with Diaryliodonium Salts

Authors

Joseph W. Graskemper, University of Nebraska-LincolnFollow
Bijia Wang, University of Nebraska - Lincoln
Linlin Qin, University of Nebraska - Lincoln
Kiel D. Neumann, University of Nebraska - Lincoln
Stephen G. DiMagno, University of Nebraska-LincolnFollow

Date of this Version

5-2011

Comments

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

Abstract

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.

Includes Supporting Information (50 pp.)