Double-fold C-H oxygenation of arenes using PyrDipSi: A general and efficient traceless/modifiable silicon-tethered directing group

Anton V. Gulevich, Ferdinand S. Melkonyan, Dhruba Sarkar, Vladimir Gevorgyan

Research output: Contribution to journalArticle

100 Scopus citations

Abstract

The efficient Pd-catalyzed double-fold C-H oxygenation of arenes into resorcinols using the newly developed 2-pyrimidyldiisopropylsilyl (PyrDipSi) directing group is described. Its use allows for the sequential introduction of OAc and OPiv groups in a one-pot manner to produce orthogonally protected resorcinol derivatives. The PyrDipSi group is superior to the previously developed 2-pyridyldiisopropylsilyl (PyDipSi) group, as it is efficient for monooxygenation of ortho-substituted arenes. Notably, the PyrDipSi group can be easily installed into arene molecules and can be easily removed or modified after the oxygenation reaction.

Original languageEnglish (US)
Pages (from-to)5528-5531
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number12
DOIs
StatePublished - Mar 28 2012

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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