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 language | English |
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Pages (from-to) | 6140-6143 |
Number of pages | 4 |
Journal | Journal of the American Chemical Society |
Volume | 137 |
Issue number | 19 |
DOIs | |
Publication status | Published - May 20 2015 |
Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry