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

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

Research output: Contribution to journalArticle

38 Citations (Scopus)

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
StatePublished - Jun 17 2011

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Fluorination
fluorination
Halogenation
Fluorides
Salts
Electrons
Ligands
salts
fluorides
elimination
chemistry
ligands
rings
electronics
electrons

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Unprecedented directing group ability of cyclophanes in arene fluorinations with diaryliodonium salts. / Graskemper, Joseph W.; Wang, Bijia; Qin, Linlin; Neumann, Kiel D.; DiMagno, Stephen.

In: Organic Letters, Vol. 13, No. 12, 17.06.2011, p. 3158-3161.

Research output: Contribution to journalArticle

Graskemper, JW, Wang, B, Qin, L, Neumann, KD & DiMagno, S 2011, 'Unprecedented directing group ability of cyclophanes in arene fluorinations with diaryliodonium salts', Organic Letters, vol. 13, no. 12, pp. 3158-3161. https://doi.org/10.1021/ol201080c
Graskemper, Joseph W. ; Wang, Bijia ; Qin, Linlin ; Neumann, Kiel D. ; DiMagno, Stephen. / Unprecedented directing group ability of cyclophanes in arene fluorinations with diaryliodonium salts. In: Organic Letters. 2011 ; Vol. 13, No. 12. pp. 3158-3161.
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