Ruthenium-Catalyzed Oxidant-Free Allylation of Aromatic Ketoximes with Allylic Acetates at Room Temperature

Rajendran Manikandan, Padmaja Madasamy, Masilamani Jeganmohan

Research output: Contribution to journalArticlepeer-review

58 Scopus citations

Abstract

Substituted aromatic ketoximes reacted efficiently with allylic acetates in the presence of {[RuCl2(p-cymene)]2} and AgSbF6 in 1,2-dichloroethane at ambient temperature, providing ortho-allyl aromatic ketoximes in a highly regioselective manner without an oxidant. In the reaction, the acetate group of allyl acetate acts as a base to activate the C-H bond of aromatics. Later, ortho-allyl aromatic ketoximes were converted into ortho-allyl aromatic ketones in the presence of HCl. Substituted aromatic ketoximes reacted efficiently with allylic acetates in the presence of [{RuCl2(p-cymene)}2] and AgSbF6 in 1,2-dichloroethane at ambient temperature, providing ortho-allyl aromatic ketoximes in a highly regioselective manner without an oxidant. In the reaction, the acetate group of allyl acetate acts as a base to activate the C-H bond of aromatics. Later, ortho-allyl aromatic ketoximes were converted into ortho-allyl aromatic ketones in the presence of HCl.

Original languageEnglish
Pages (from-to)13934-13938
Number of pages5
JournalChemistry - A European Journal
Volume21
Issue number40
DOIs
StatePublished - 1 Sep 2015
Externally publishedYes

Keywords

  • C-H activation
  • allylation
  • allylic compounds
  • ketoximes
  • ruthenium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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