Journal
ORGANIC LETTERS
Volume 13, Issue 12, Pages 3158-3161Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol201080c
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Funding
- National Science Foundation [CHE 0717562]
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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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