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Published on: March 24, 2018
Fluorinations of unsymmetrical diaryliodonium salts containing ortho-sidearms; influence of sidearm on selectivity
Ahmed M H Abudken1, Eric G Hope2, Kuldip Singh2
1School of Chemistry, University of Leicester, Leicester, LE1 7RH, UK. Alison.Stuart@le.ac.uk and College of Pharmacy, Al-Qadisiyah University, Al-Qadisiyah, Iraq.
Abstract:
Activated aromatics were reacted with two different fluoroidoane reagents 1 and 2 in the presence of triflic acid to prepare only the para-substituted diaryliodonium salts. With fluoroiodane 1 the unsymmetrical diaryliodonium salts contained an ortho-propan-2-ol sidearm, whereas the alcohol sidearm was eliminated to form an ortho-styrene sidearm in the reaction with fluoroiodane 2. Only the diaryliodonium salts containing a styrene sidearm were fluorinated successfully to deliver para-fluorinated aromatics in good yields.
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