Palladium-catalyzed oxirane-opening reaction with arenes via C-H bond activation

Zhen Wang, Yoichiro Kuninobu, Motomu Kanai

Research output: Contribution to journalArticle

56 Citations (Scopus)

Abstract

We achieved a palladium-catalyzed C-H activation/C-C coupling reaction between arenes with a pyridyl, aminoquinolinyl, imino, or amide directing group, and oxiranes. The reaction proceeded at room temperature without any additives and tolerated a wide variety of functional groups, and the products were obtained in good to excellent yields, even on gram scale. This is the first example of a transition-metal-catalyzed intermolecular direct coupling reaction between a C-H bond of aromatic compounds and a carbon atom of oxiranes via C-H bond activation. By using N-methoxybenzamide as a substrate, we obtained 3-substituted isochroman-1-ones in one pot. The coupling reaction proceeded with stereoretention. Kinetic isotope effect experiments suggested that C-H bond activation is the rate-determining step.

Original languageEnglish
Pages (from-to)6140-6143
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number19
DOIs
Publication statusPublished - May 20 2015
Externally publishedYes

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Ethylene Oxide
Epoxy Compounds
Palladium
Chemical activation
Amides
Isotopes
Carbon
Aromatic compounds
Metals
Functional groups
Temperature
Transition metals
Atoms
Kinetics
Substrates
Experiments

All Science Journal Classification (ASJC) codes

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

Cite this

Palladium-catalyzed oxirane-opening reaction with arenes via C-H bond activation. / Wang, Zhen; Kuninobu, Yoichiro; Kanai, Motomu.

In: Journal of the American Chemical Society, Vol. 137, No. 19, 20.05.2015, p. 6140-6143.

Research output: Contribution to journalArticle

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