Unprecedented directing group ability of cyclophanes in arene fluorinations with diaryliodonium salts

Joseph W. Graskemper, Bijia Wang, Linlin Qin, Kiel D. Neumann, Stephen G. Dimagno

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39 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)3158-3161
Number of pages4
JournalOrganic Letters
Volume13
Issue number12
DOIs
Publication statusPublished - Jun 17 2011

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Graskemper, J. W., Wang, B., Qin, L., Neumann, K. D., & Dimagno, S. G. (2011). Unprecedented directing group ability of cyclophanes in arene fluorinations with diaryliodonium salts. Organic Letters, 13(12), 3158-3161. https://doi.org/10.1021/ol201080c