A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts

Linlin Qin, Bao Hu, Kiel D. Neumann, Ethan J. Linstad, Katelyenn McCauley, Jordan Veness, Jayson J. Kempinger, Stephen G. DiMagno

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Diaryliodonium salts are powerful and widely used arylating agents in organic chemistry. Here we report a scalable synthesis of densely functionalized diaryliodonium salts from aryl iodides under mild conditions. This two-step, one-pot process has remarkable functional group tolerance, is compatible with commonly employed acid-labile protective group strategies, avoids heavy metal and transition metal reagents, and provides a direct route to stable precursors to PET imaging agents.

Original languageEnglish (US)
Pages (from-to)5919-5924
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number27
DOIs
StatePublished - Sep 1 2015

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Salts
salts
organic chemistry
Iodides
synthesis
heavy metals
Heavy Metals
iodides
Functional groups
Transition metals
reagents
transition metals
routes
Imaging techniques
acids
Acids
metals
Organic Chemistry

Keywords

  • Aryl iodides
  • Iodane synthesis
  • Iodine
  • Iodonium salts
  • Oxidation
  • Synthetic methods

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Qin, L., Hu, B., Neumann, K. D., Linstad, E. J., McCauley, K., Veness, J., ... DiMagno, S. G. (2015). A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts. European Journal of Organic Chemistry, 2015(27), 5919-5924. https://doi.org/10.1002/ejoc.201500986

A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts. / Qin, Linlin; Hu, Bao; Neumann, Kiel D.; Linstad, Ethan J.; McCauley, Katelyenn; Veness, Jordan; Kempinger, Jayson J.; DiMagno, Stephen G.

In: European Journal of Organic Chemistry, Vol. 2015, No. 27, 01.09.2015, p. 5919-5924.

Research output: Contribution to journalArticle

Qin, L, Hu, B, Neumann, KD, Linstad, EJ, McCauley, K, Veness, J, Kempinger, JJ & DiMagno, SG 2015, 'A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts', European Journal of Organic Chemistry, vol. 2015, no. 27, pp. 5919-5924. https://doi.org/10.1002/ejoc.201500986
Qin, Linlin ; Hu, Bao ; Neumann, Kiel D. ; Linstad, Ethan J. ; McCauley, Katelyenn ; Veness, Jordan ; Kempinger, Jayson J. ; DiMagno, Stephen G. / A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts. In: European Journal of Organic Chemistry. 2015 ; Vol. 2015, No. 27. pp. 5919-5924.
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