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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Unprecedented directing group ability of cyclophanes in arene fluorinations with diaryliodonium salts
Joseph W Graskemper1, Bijia Wang, Linlin Qin
1Department of Chemistry and Nebraska Center for Materials and Nanoscience, University of Nebraska, Lincoln, Nebraska 68588-0304, USA.
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.
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