Palladium-catalyzed coupling reactions of paramagnetic vinyl halides

T. Kalai, Mária Balog, J. Jekó́, Wayne L. Hubbell, K. Hideg

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

Suzuki, Heck and Sonogishira coupling reactions of paramagnetic vinyl bromides 1-6 gave monofunctional (7a,b), homobifunctional (8a,b, 24), and heterobifunctional pyrroline nitroxides (9-19, 31) under mild conditions in a one-step reaction. From these compounds thiol-specific spin labels 26 and 28 and pyrroline nitroxide annulated heterocycles 30 and 32 were synthesized. The ethynyl derivative of pyrroline nitroxide 33 also can be used as an acetylene reactant in Larock indole synthesis to give the paramagnetic indole derivative 36.

Original languageEnglish
Pages (from-to)2365-2372
Number of pages8
JournalSynthesis
Issue number16
Publication statusPublished - 2002

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Palladium
Derivatives
Acetylene
Spin Labels
Labels
Sulfhydryl Compounds
pyrroline
indole

Keywords

  • Alkynes
  • Free radical
  • Heterocycles
  • Palladium
  • Suzuki reaction

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Palladium-catalyzed coupling reactions of paramagnetic vinyl halides. / Kalai, T.; Balog, Mária; Jekó́, J.; Hubbell, Wayne L.; Hideg, K.

In: Synthesis, No. 16, 2002, p. 2365-2372.

Research output: Contribution to journalArticle

Kalai, T. ; Balog, Mária ; Jekó́, J. ; Hubbell, Wayne L. ; Hideg, K. / Palladium-catalyzed coupling reactions of paramagnetic vinyl halides. In: Synthesis. 2002 ; No. 16. pp. 2365-2372.
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