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 |
|---|---|
| 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 |
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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 journal › Article
}
TY - JOUR
T1 - Palladium-catalyzed oxirane-opening reaction with arenes via C-H bond activation
AU - Wang, Zhen
AU - Kuninobu, Yoichiro
AU - Kanai, Motomu
PY - 2015/5/20
Y1 - 2015/5/20
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84930207984&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84930207984&partnerID=8YFLogxK
U2 - 10.1021/jacs.5b02435
DO - 10.1021/jacs.5b02435
M3 - Article
C2 - 25924012
AN - SCOPUS:84930207984
VL - 137
SP - 6140
EP - 6143
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 19
ER -